Reaction Attempts

Reaction Attempts Nature Precedings : doi:10.1038/npre.2010.4416.1 : Posted 4 May 2010

The UsefulChem Project

Compiled and Performed by: Jean-Claude Bradley, Khalid Mirza, and Andrew Lang with Tim Bohinski, David Bulger, Alicia Merchant, Emily Messner, Marshall Moritz, Shannon Oseback, Rikesh Parikh, Mitesh Shah

Version: April 28, 2010 Licensed under a Creative Commons Attribution 2.5 License Data is available as CC0

1

Preface Reaction Attempts First Edition Data Source: the UsefulChem project Introduction Open Notebook Science (ONS) refers to the practice of making the full contents of a laboratory notebook and all associated raw data files available in near real time.[1] This represents an opportunity for everyone to benefit from work in progress in an open research group. However, in order to make use of the information, it must be easily discoverable. A simple strategy to increase discoverability is redundancy over multiple communication platforms. In another project - the Open Notebook Science Solubility Challenge[2] - we published non-aqueous solubility data in the form of physical and downloadable (PDF) books.[3] Although it is possible to search the solubility database using web query interfaces, exploration of a Google Spreadsheet, an XML feed, etc.[4], having a physical copy in the laboratory has proved to be very convenient in several instances. A similar format for reactions will also be useful.

The UsefulChem Project

Nature Precedings : doi:10.1038/npre.2010.4416.1 : Posted 4 May 2010

UsefulChem started in 2005 as an organic chemistry Open Notebook Science project with a main goal of discovering new anti-malarial agents that can be prepared by simple and cheap syntheses.[5] Most of the reactions on UsefuChem are Ugi reactions, which involve the mixing of an amine, aldehyde, carboxylic acid and isonitrile in a solvent at room temperature generally for a few hours to days.[6] The multicomponent design of the Ugi reaction and the simple reaction conditions make it ideal for exploring large virtual libraries and selecting compounds of interest to make.[7] Isolation of the Ugi products can be immensely simpler, cheaper and readily scalable if they precipitate in pure form from the reaction mixture. To this end, much of the research in the UsefulChem project focuses on reaction conditions that lead to this outcome.[8] This is in fact the origin of the ONS Solubility Challenge discussed above.[9]

The Reaction Attempts Database In order to look for patterns in the reaction conditions which led to Ugi product precipitation, the CombiUgiResults Google Spreadsheet was set up.[10] Reactions indexed there can be sorted by precipitation outcome, solvent, reactant, concentration, etc. and links to the laboratory notebook pages can be followed for full details. However, this sheet is designed specifically for Ugi reactions and contains columns specifically for the aldehyde, amine, carboxylic acid and isonitrile. In order to enable the tracking of other types of reactions, the information in the CombiUgiResults sheet was reformatted into two other sheets: ReactionAttempts[11] (containing reagents and reactants) and RXIDsReactionAttempts[12] (containing reaction conditions and results, such as solvent, concentration of limiting reactant, appearance of a precipitate, yield, etc.). The two sheets are connected via the use of a common ReactionID. This format permits the representation of any type of reaction, with an unlimited number of reactants and products.[13] By definition, any Open Notebook Science project in a work in progress. The listing of a reaction in this database only means that the researcher attempted or is in the process of attempting it. Whatever the situation, a link to the laboratory notebook page is provided, where the most recent information is available. The philosophy used here is that partial information is always better than no information at all. Thus a researcher investigating the prior use a particular reactant in a Ugi reaction might find the report that a precipitate was obtained in methanol helpful for designing their own reactions, even if the characterization of the precipitate is still pending. At the very least, knowing that a certain researcher has at least attempted a similar reaction is enough information for initiating a discussion, which may lead to valuable insights.

Reaction Attempts on Chemspider Although SMILES[14] are provided in the spreadsheets, the primary key to identify compounds is the ChemSpider ID (CSID)[15]. This allows us to render molecule images in the book automatically. In the case of the ONS Solubility Challenge book[3], use of the CSID enables a convenient way to calculate various descriptors for displaying values in the book. In addition, the compounds in the Reaction Attempts database are indexed on ChemSpider as two Data Sources: ReactantsAttemptedReactions and ProductsAttemptedReactions[13]. In this way a substructure search for either reactants or products will identify indexed molecules. Clicking on the Syntheses tab in the ChemSpider record for a selected molecule will then reveal a list of hyperlinks to the relevant laboratory notebook pages.

Organization of the Book In keeping with the layout of the ONS Solubility Challenge Book, the reactants are listed in alphabetical order. Each entry displays the list of reactions where the reactant was used. This includes a scheme with all reactants and product as well as key metadata: the researcher, reaction type, solvent, limiting reactant concentration, observation of a precipitate, comments and a reference (links to the laboratory notebook page). In this edition, only Ugi reactions are included. The reaction schemes are laid out in the following order: carboxylic acid, amine, aldehyde and isonitrile. This should allow for easy comparison between schemes within a given record. Reactions where the Ugi product was isolated and characterized are marked with a green check and the percent yield is noted. Since the Ugi products do not have simple common names, they are not included as separate entries. However, all reactions where the synthesis of a specific Ugi product was attempted can be found by looking up the entries for any of the four reactants. Although this compilation is not exhaustive, it does cover the vast majority of reactions in the UsefulChem project to date. Future editions will include other reactions from UsefulChem and other sources.

Archive This edition is linked to the UsefulChem interactive data archive (ZIP)[16], (DVD)[17], ReactionAttempts (XLS)[18] and RXIDsReactionAttempts(XLS)[19] taken on 2010-04-27.

References 1. Open Notebook Science Wikipedia Entry http://en.wikipedia.org/wiki/Open_Notebook_Science 2. Open Notebook Science Solubility Challenge Wiki http://onschallenge.wikispaces.com 3. Bradley, J.-C. First Edition of ONS Solubility Challenge Book UsefulChem Blog (2009)

2


http://usefulchem.blogspot.com/2009/12/first-edition-of-ons-solubility.html 4. Open Notebook Science Solubility Challenge List of Experiments page http://onschallenge.wikispaces.com/list+of+experiments 5. UsefulChem Wiki http://usefulchem.wikispaces.com 6. Ugi Reaction Wikipedia Entry http://en.wikipedia.org/wiki/Ugi_reaction 7. Dömling, A., & Ugi, I. (2000). Multicomponent Reactions with Isocyanides. Angewandte Chemie International English Edition, 39(18), 3168-3210. doi: 10.1002/1521-3773(20000915)39:183.0.CO;2-U. 8. UsefulChem List of Experiments http://usefulchem.wikispaces.com/All+Reactions 9. Bradley, J.-C. Open Notebook Science Challenge UsefulChem Blog (2008) http://usefulchem.blogspot.com/2008/09/open-notebook-science-challenge.html 10. CombiUgiResults Google Spreadsheet http://spreadsheets.google.com/ccc?key=plwwufp30hfpUERhse9y5Kw 11. ReactionAttempts Google Spreadsheet http://spreadsheets.google.com/ccc?key=0Ak1R8T6wt4YQdG9NejNLcDNUMkVBVURGM01TR0NxdXc 12. RXIDsReactionAttempts Google Spreadsheet http://spreadsheets.google.com/ccc?key=0Ak1R8T6wt4YQdGVENVFMWjdzaGd2REJTTnA4RG5vblE 13. Bradley, J.-C. Reaction Attempts on ChemSpider UsefulChem Blog (2010) http://usefulchem.blogspot.com/2010/03/reaction-attempts-on-chemspider.html 14. SMILES Wikipedia Entry http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification 15. ChemSpider Web Site http://www.chemspider.com/ 16. UC archive Drexel server (ZIP) http://showme.physics.drexel.edu/usefulchem/archives/usefulchem2010-04-27.zip 17. UC archive on lulu.com (DVD) http://www.lulu.com/product/dvd/usefulchem-archive/10791847 18. Bradley, J.-C.; Lang, A.. Reaction Attempts Reactants and Products. UsefulChem. 2010-04-27. URL:http://spreadsheets.google.com/pub?key=toMz3Kp3T2EAUDF3MSGCquw&output=xls. Accessed: 2010-04-27. (Archived by WebCite® at http://www.webcitation.org/5pIsFEbT9) 19. Bradley, J.-C.; Lang, A.. Reaction Attempts RXIDs. UsefulChem. 2010-04-27. URL:http://spreadsheets.google.com/pub?key=teD5QLZ7shgvDBSNp8DnonQ&output=xls. Accessed: 2010-04-27. (Archived by WebCite® at http://www.webcitation.org/5pIs2eh62)

Reactions 1-aminocyclohexane-1-carboxylic acid Reaction ID UCEXP233-1 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 0.921 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp233

+

1-aminocyclohexane-1carboxylic acid

+

benzylamine

+

3,5-dimethoxybenzaldehyde

→

t-butyl isocyanide

24534439

Reaction ID UCEXP233-2 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 0.92 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp233

+


+

benzylamine

+


Reaction ID UCEXP233-7 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 1.02 M Precipitate No Comments -

3

→

cyclohexylisocyanide

24534440

Reference

http://usefulchem.wikispaces.com/Exp233

+


+

benzylamine

+


→

t-butyl isocyanide

24534439

Reaction ID UCEXP233-8


Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 1.018 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp233

+


+

benzylamine

+


→


24534440

1-heptylamine Reaction ID UCEXP131-4 Researcher Rikesh Parikh Reaction Type Ugi Solvent methanol Limiting Reactant 0.612 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp131

+

Boc-Trp-OH

+

1-heptylamine

+

o-vanillin

→

benzyl isocyanide

21106061

Reaction ID UCEXP131-8 Researcher Rikesh Parikh Reaction Type Ugi Solvent methanol Limiting Reactant 0.618 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp131

+

Boc-Trp-OH

+

1-heptylamine

+

o-vanillin

Reaction ID UCEXP131-9 Researcher Reaction Type Solvent

Rikesh Parikh Ugi methanol

4

→

n-butyl isocyanide

21106065

Limiting Reactant 0.61 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp131

+

Boc-Trp-OH

+

+

1-heptylamine

o-vanillin

→

1-pentyl isocyanide

21106066

Reaction ID UCEXP148A-V1B153


Researcher Khalid Mirza/ Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.398 M Precipitate Yes but the aldehyde alone is not soluble in methanol Yield 50.1 % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp148

+

crotonic acid

+

1-heptylamine

+

phenanthrene-9-carboxaldehyde

→

t-butyl isocyanide

21106058

Reaction ID UCEXP180 Researcher Shannon Oseback Reaction Type Ugi Solvent methanol Limiting Reactant 0.403 M Precipitate no and aldehyde alone not solube Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp180

+

acetic acid

+

1-heptylamine

+


→

n-butyl isocyanide

21105834

Reaction ID UCEXP182 Researcher Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.398 M Precipitate Reactants Insoluble Comments Reference http://usefulchem.wikispaces.com/Exp182

+

furoic acid

+

1-heptylamine

+


Reaction ID UCEXP215A Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.661 M

5

→

n-butyl isocyanide

21168529

Precipitate Comments Reference

No http://usefulchem.wikispaces.com/Exp215

+

crotonic acid

+

1-heptylamine

+


→

t-butyl isocyanide

21106058



Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.833 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp231

+

glycolic acid

+

1-heptylamine

+

2-methoxy-1-naphthaldehyde

→

tosylmethyl isocyanide

24528188

Reaction ID UCExp236-15 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.614 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp236

+

3,3'-dichloropivalic acid

+

1-heptylamine

+

4-(trifluoromethyl)benzaldehyde

→

t-butyl isocyanide

24528288

Reaction ID UCExp238-08 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.74 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp238

+

crotonic acid

+

1-heptylamine

+


Reaction ID UCExp238-20 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.775 M Precipitate No Comments -

6

→


24528310

Reference


+

crotonic acid

+

1-heptylamine

+


→

t-butyl isocyanide

21106058

Reaction ID UCExp238-32


Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.572 M Precipitate Yes Product Awaiting Characterization Comments Reference http://usefulchem.wikispaces.com/Exp238

+

Boc-Gly-OH

+

1-heptylamine

+


→


24528332

Reaction ID UCExp238-44 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.6 M Precipitate Yes Product Awaiting Characterization Comments Reference http://usefulchem.wikispaces.com/Exp238

+

Boc-Gly-OH

+

1-heptylamine

+


→

t-butyl isocyanide

24528344


+

3,4methylenedioxyphenylacetic acid

+

1-heptylamine

+


Reaction ID UCExp241-47 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.715 M

7

→

n-butyl isocyanide

24528377



+


+

1-heptylamine

+


→

t-butyl isocyanide

24528380

1-hexylamine



+

formic acid

+

1-hexylamine

+

2-naphthaldehyde

→

1-pentyl isocyanide

21106078


+

Boc-Trp-OH

+

1-hexylamine

+

o-vanillin

→

n-butyl isocyanide

21106063


+

Boc-Trp-OH

+

1-hexylamine

+

o-vanillin

Reaction ID UCEXP181-064V2 Researcher

Khalid Mirza

8

→

1-pentyl isocyanide

21106064

Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+

3-methylbut-2-enoic acid

+

1-hexylamine

+

3,4-dihydroxybenzaldehyde

→


24528103


Reaction ID UCEXP181-078V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.219 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+

1-pyrenebutyric acid

+

1-hexylamine

+

2-hydroxybenzaldehyde

→

t-butyl isocyanide

24528114

Reaction ID UCEXP181-109V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.22 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+

4-hydroxybenzoic acid

+

1-hexylamine

+

3-methoxybenzaldehyde

→


24528139

Reaction ID UCEXP229-2 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 0.667 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp229

+

Boc-Trp-OH

+

1-hexylamine

+

benzaldehyde

Reaction ID UCExp236-07 Researcher Reaction Type Solvent

Khalid Mirza Ugi methanol

9

→

n-butyl isocyanide

24528183

Limiting Reactant 0.614 M Precipitate Yes Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp236

+


+

1-hexylamine

+


→

t-butyl isocyanide

24528280



+

methacrylic acid

+

1-hexylamine

+


→

t-butyl isocyanide

24528301


+

crotonic acid

+

1-hexylamine

+


→


24528311


+

crotonic acid

+

1-hexylamine

+


Reaction ID UCExp238-33 Researcher

Khalid Mirza

10

→

t-butyl isocyanide

24528321

Reaction Type Ugi Solvent THF Limiting Reactant 1.616 M Precipitate Yes Product Awaiting Characterization Comments Reference http://usefulchem.wikispaces.com/Exp238

+

Boc-Gly-OH

+

1-hexylamine

+


→


24528333



+


+

1-hexylamine

+


→

n-butyl isocyanide

24528366

1-octylamine Reaction ID UCEXP131-5 Researcher Rikesh Parikh Reaction Type Ugi Solvent methanol Limiting Reactant 0.605 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp131

+

Boc-Trp-OH

+

1-octylamine

+

o-vanillin

→

benzyl isocyanide

21106062


+

Boc-Trp-OH

+

1-octylamine

+

o-vanillin

11

→

n-butyl isocyanide

21106072


+

Boc-Trp-OH

+

1-octylamine

+

o-vanillin

→

1-pentyl isocyanide

21106073


1-pentyl isocyanide Reaction ID UCEXP130-2 Researcher Rikesh Parikh Reaction Type Ugi Solvent methanol Limiting Reactant 0.728 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp130

+

formic acid

+

1-hexylamine

+

2-naphthaldehyde

→

1-pentyl isocyanide

21106078


+

Boc-Trp-OH

+

furfurylamine

+

veratraldehyde

→

1-pentyl isocyanide

21106068


+

+

+

12

→

Boc-Trp-OH

5-methylfurfurylamine

veratraldehyde

1-pentyl isocyanide

21106069



+

Boc-Trp-OH

+

1-hexylamine

+

o-vanillin

→

1-pentyl isocyanide

21106064


+

Boc-Trp-OH

+

1-heptylamine

+

o-vanillin

→

1-pentyl isocyanide

21106066


+

Boc-Trp-OH

+

1-propylamine

+

o-vanillin


13

→

1-pentyl isocyanide

21106071

+

Boc-Trp-OH

+

1-octylamine

+

o-vanillin

→

1-pentyl isocyanide

21106073

Reaction ID UCEXP225-3 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.888 M Precipitate Yes Product Pending Comments 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid Reference http://usefulchem.wikispaces.com/Exp225


+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

1-pentyl isocyanide

24528159

Reaction ID UCEXP226-3 Researcher David Bulger Reaction Type Ugi Solvent THF Limiting Reactant 0.519 M Precipitate No Comments 0.5 mmol of isocyanide was added to 900uL of a 0.55M solution of aldehyde; amine and acid Reference http://usefulchem.wikispaces.com/Exp226

+


+


+

benzaldehyde

→

1-pentyl isocyanide

24528167

Reaction ID UCEXP227-3 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.444 M Precipitate No Comments 0.5 mmol of isocyanide was added to 500uL of a 0.5M solution of aldehyde; amine and acid Reference http://usefulchem.wikispaces.com/Exp227

+


+

furfurylamine

+

piperonal

Reaction ID UCEXP232-03 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.099 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp232

14

→

1-pentyl isocyanide

24528175

+

Boc-Gly-OH

+

+

furfurylamine

benzaldehyde

→

1-pentyl isocyanide

24528190



+

Boc-Gly-OH

+

+

furfurylamine

4-methylbenzaldehyde

→

1-pentyl isocyanide

24528195

Reaction ID UCEXP232-13 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.029 M Precipitate Yes Product Pending Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528200


+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde


15

→

1-pentyl isocyanide

24528204

+

Boc-Gly-OH

+

+

furfurylamine

diphenylacetaldehyde

→

1-pentyl isocyanide

24528209



+

Boc-Gly-OH

+

furfurylamine

+

cyclohexancarboxaldehyde

→

1-pentyl isocyanide

24528214


+

Boc-Gly-OH

+

+

furfurylamine

2-furaldehyde

→

1-pentyl isocyanide

24528219


+

Boc-Gly-OH

+

furfurylamine

+



16

→

1-pentyl isocyanide

24528224

+

Boc-Gly-OH

+

+

furfurylamine

o-tolualdehyde

→

1-pentyl isocyanide

24528229



+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528234


+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

→

1-pentyl isocyanide

24528239


+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal


17

→

1-pentyl isocyanide

24528243

+

Boc-Gly-OH

+

furfurylamine

+

2-phenylpropionaldehyde

→

1-pentyl isocyanide

24534418



+

Boc-Gly-OH

+

+

furfurylamine

m-anisaldehyde

→

1-pentyl isocyanide

24528253


+

Boc-Gly-OH

+

+

furfurylamine

2-ethylbutyraldehyde

→

1-pentyl isocyanide

24528258

Reaction ID UCExp240-06 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.559 M Precipitate Yes Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp240

+

phenylacetic acid

+

furfurylamine

+


Reaction ID UCExp240-12 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.776 M Precipitate Yes but 48h Comments Reference http://usefulchem.wikispaces.com/Exp240

18

→

1-pentyl isocyanide

24528347

+

phenylacetic acid

+


+


→

1-pentyl isocyanide

24528351



+

+


+

methylamine

veratraldehyde

→

1-pentyl isocyanide

24528358


+

+


+

methylamine

veratraldehyde

→

1-pentyl isocyanide

24528358

Reaction ID UCExp242-10 Researcher Marshall Moritz Reaction Type Ugi Solvent benzene Limiting Reactant 0.424 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp242

+

phenylacetic acid

+


+


Reaction ID UCExp242-5 Researcher Marshall Moritz Reaction Type Ugi Solvent benzene Limiting Reactant 0.432 M Precipitate No Comments -

19

→

1-pentyl isocyanide

24528382

Reference


+

phenylacetic acid

+

furfurylamine

+


→

1-pentyl isocyanide

24528386

1-propylamine Reaction ID UCEXP134-1


Researcher Rikesh Parikh Reaction Type Ugi Solvent methanol Limiting Reactant 0.645 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp134

+

Boc-Trp-OH

+

+

1-propylamine

o-vanillin

→

n-butyl isocyanide

21106070


+

Boc-Trp-OH

+

+

1-propylamine

o-vanillin

→

1-pentyl isocyanide

21106071

Reaction ID UCEXP167A-V1B12 Researcher Tim Bohinsky Reaction Type Ugi Solvent methanol Limiting Reactant 0.403 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp167

+


+

1-propylamine

+


Reaction ID UCEXP174G/V2B39 Researcher Reaction Type Solvent


20

→

n-butyl isocyanide

21105597


+

3,4-dihydroxyphenylacetic acid

+

+

1-propylamine


→


21106199

Reaction ID UCEXP177


Researcher Shannon Oseback Reaction Type Ugi Solvent methanol Limiting Reactant 0.224 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp177

+

phenylacetic acid

+

1-propylamine

+


→

n-butyl isocyanide

21105831


+


+

1-propylamine

+


→


24528102


+

diphenylacetic acid

+

1-propylamine

+




21

→

n-butyl isocyanide

24528112

Limiting Reactant 0.614 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp236

+


+

1-propylamine

+


→

n-butyl isocyanide

24528286



Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.965 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp238

+

crotonic acid

+

1-propylamine

+


→


24528313


+

crotonic acid

+

1-propylamine

+


→

t-butyl isocyanide

24528323


+

Boc-Gly-OH

+

1-propylamine

+



22

→


24528335



+


+

1-propylamine

+

2,4-dimethylbenzaldehyde

→

t-butyl isocyanide

24528375



Reaction ID UCEXP147-3V2B6 Researcher Mitesh Shah Reaction Type Ugi Solvent methanol Limiting Reactant 0.662 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp+147

+


+

methylamine

+

2-naphthaldehyde

→

t-butyl isocyanide

21105841

Reaction ID UCEXP171B/V2B2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.219 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+


+

o-vanillin

→

t-butyl isocyanide

21106056

Reaction ID UCEXP171D/V2B4 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.219 M Precipitate Yes Product No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

benzylamine

+

o-vanillin

Reaction ID UCEXP171FV2B6

23

→

t-butyl isocyanide

21105846

Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate Yes but reactants initially insoluble Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

+

methylamine

2-naphthaldehyde

→

t-butyl isocyanide

21105841


Reaction ID UCEXP171KV2B11 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate Yes Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

methylamine

+

4-(dimethylamino)benzaldehyde

→

t-butyl isocyanide

21105842

Reaction ID UCEXP171LV2B-12 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.22 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

methylamine

+


→

t-butyl isocyanide

21106039

Reaction ID UCEXP173B/V2B14 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes but reactants initially insoluble Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

methylamine

+


24

→

t-butyl isocyanide

21105844

Reaction ID UCEXP173C/V2B15 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

methylamine

+


→

t-butyl isocyanide

21106044


Reaction ID UCEXP173D/V2B16 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.224 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

methylamine

+


→

n-butyl isocyanide

21106048

Reaction ID UCEXP173J/V2B22 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.224 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

methylamine

+


→

t-butyl isocyanide

21106038

Reaction ID UCEXP173P/V2B28 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

methylamine

+


Reaction ID UCEXP181-070V2

25

→

t-butyl isocyanide

21106050

Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.22 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+


+

+

3-chloroaniline


→

n-butyl isocyanide

24528530



+


+

1-hexylamine

+


→

t-butyl isocyanide

24528114


+


+

+

aniline

benzaldehyde

→

n-butyl isocyanide

21106208


+


+

methylamine

+


Reaction ID UCEXP215C Researcher Reaction Type

Khalid Mirza Ugi

26

→

t-butyl isocyanide

21106206

Solvent THF Limiting Reactant 0.662 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp215

+


+

+

methylamine

2-naphthaldehyde

→

t-butyl isocyanide

21105841

Reaction ID UCEXP215D



+


+

methylamine

+


→

t-butyl isocyanide

21105842

Reaction ID UCEXP222-5 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.898 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp222

+


+

methylamine

+


→

t-butyl isocyanide

21105842


+


+

methylamine

+


Reaction ID UCEXP226-1 Researcher David Bulger Reaction Type Ugi Solvent THF Limiting Reactant 0.523 M

27

→

t-butyl isocyanide

21105844


No 0.5 mmol of isocyanide was added to 900uL of a 0.55M solution of aldehyde; amine and acid http://usefulchem.wikispaces.com/Exp226

+


+


+

benzaldehyde

→

t-butyl isocyanide

24528165



Researcher David Bulger Reaction Type Ugi Solvent THF Limiting Reactant 0.525 M Precipitate No Comments 0.5 mmol of isocyanide was added to 900uL of a 0.55M solution of aldehyde; amine and acid Reference http://usefulchem.wikispaces.com/Exp226

+


+


+

benzaldehyde

→

n-butyl isocyanide

24528166


+


+


+

benzaldehyde

→

1-pentyl isocyanide

24528167


+


+


+

benzaldehyde

→


Reaction ID UCEXP226-5 Researcher David Bulger Reaction Type Ugi Solvent THF Limiting Reactant 0.52 M Precipitate No Comments 0.5 mmol of isocyanide was added to 900uL of a 0.55M solution of aldehyde; amine and acid

28

24528168

Reference


+


+


+

benzaldehyde

→

benzyl isocyanide

24528169



+


+


+

benzaldehyde

→


24528170


+


+


+

→

2-morpholinoethyl isocyanide

benzaldehyde

24528171


+


+


+

benzaldehyde

Reaction ID UCEXP227-1 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.261 M Precipitate No

29

→

2-chloro-6methylphenyl isocyanide

24528172

Comments Reference

0.5 mmol of isocyanide was added to 500uL of a 0.5M solution of aldehyde; amine and acid http://usefulchem.wikispaces.com/Exp227

+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528173



Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.453 M Precipitate No Comments 0.5 mmol of isocyanide was added to 500uL of a 0.5M solution of aldehyde; amine and acid Reference http://usefulchem.wikispaces.com/Exp227

+


+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528174


+


+

furfurylamine

+

piperonal

→

1-pentyl isocyanide

24528175


+


+

furfurylamine

+

piperonal

→



30

24528176

+


+

furfurylamine

+

piperonal

→

benzyl isocyanide

24528177



+


+

furfurylamine

+

piperonal

→


24528178


+


+

furfurylamine

+

→


piperonal

24528179


+


+

furfurylamine

+

piperonal

Reaction ID UCEXP228-7 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.67 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp228

31

→


24528180

+


+

methylamine

+


→

t-butyl isocyanide

21105844



+


+

methylamine

+

2-naphthaldehyde

→

t-butyl isocyanide

21105841

Reaction ID UCEXP231-7 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.667 M Precipitate Yes Product Pending Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp231

+


+

furfurylamine

+

2-furaldehyde

→

n-butyl isocyanide

24528187

1,1,3,3-tetramethylbutyl isocyanide Reaction ID UCEXP232-05 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.098 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde



32

→

1,1,3,3tetramethylbutyl isocyanide

24528192


+

Boc-Gly-OH

+

+

furfurylamine

→



24528197



+

Boc-Gly-OH

+

furfurylamine

+

→



24528201


+

Boc-Gly-OH

+

furfurylamine

+

→


crotonaldehyde

24528206


+

Boc-Gly-OH

+

furfurylamine

+


33

→


24528211


+

Boc-Gly-OH

+

furfurylamine

+

→



24528216



+

Boc-Gly-OH

+

+

furfurylamine

→


2-furaldehyde

24528221


+

Boc-Gly-OH

+

furfurylamine

+

→



24528226


+

+

+

34

→

Boc-Gly-OH

furfurylamine


o-tolualdehyde

24528231



Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.066 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+

→



24528236


+

Boc-Gly-OH

+

furfurylamine

+

→


hexanaldehyde

24528241


+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal

Reaction ID UCEXP232-65 Researcher Reaction Type

Khalid Mirza Ugi

35

→


24528245

Solvent methanol Limiting Reactant 1.069 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+

→



24534420



+

Boc-Gly-OH

+

+

furfurylamine

→


m-anisaldehyde

24528255


+

Boc-Gly-OH

+

+

furfurylamine

→



24528260


+

phenylacetic acid

+

furfurylamine

+


36

→


21782583


+

phenylacetic acid

+


+

→



24528349



+


+

methylamine

+

→


veratraldehyde

24528357


+


+

methylamine

+

→


veratraldehyde

24528357

Reaction ID UCExp242-4 Researcher Marshall Moritz Reaction Type Ugi Solvent benzene Limiting Reactant 0.414 M Precipitate Yes Product No Comments Reference http://usefulchem.wikispaces.com/Exp242

+

+

+

37

→

phenylacetic acid

furfurylamine



24528385



Researcher Marshall Moritz Reaction Type Ugi Solvent benzene Limiting Reactant 0.406 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp242

+

phenylacetic acid

+


+

→



24528390


+


+

furfurylamine

+

→


piperonal

24528395


+


+

furfurylamine

+

piperonal

Reaction ID UCExp245-15 Researcher Reaction Type

Khalid Mirza Ugi

38

→


24528395


+


+


+

→


piperonal

24528398



+


+


+

→


piperonal

24528398


+

cbz-proline

+

furfurylamine

+

→


piperonal

24528403


+

cbz-proline

+

furfurylamine

+

piperonal

39

→


24528403


+

cbz-proline

+


+

→


piperonal

24528405



+

cbz-proline

+


+

→


piperonal

24528405


+


+

furfurylamine

+

→


piperonal

24528408


+

+

+

40

→


furfurylamine


piperonal

24528408

2-chloro-6-methylphenyl isocyanide Reaction ID UCEXP225-8


Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.868 M Precipitate No Comments 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid Reference http://usefulchem.wikispaces.com/Exp225

+

Boc-Gly-OH

+

furfurylamine

+

→


piperonal

24528164


+


+


+

→


benzaldehyde

24528172


+


+

furfurylamine

+

piperonal

41

→


24528180

2-chloroaniline Reaction ID UCEXP173N/V2B26 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.217 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+

decanoic acid

+

+

2-chloroaniline

o-vanillin

→


21105847



+


+

+

2-chloroaniline

2-naphthaldehyde

→

t-butyl isocyanide

24528117


+

decanoic acid

+

2-chloroaniline

+


→


24528124


+

+

+

42

→


2-chloroaniline



24528130


+


+

+

2-chloroaniline

veratraldehyde

→


24534443



+


+

2-chloroaniline

+


→

t-butyl isocyanide

24528282


+

crotonic acid

+

2-chloroaniline

+


→


24528303


+

crotonic acid

+

2-chloroaniline

+


43

→

t-butyl isocyanide

24528315


+

Boc-Gly-OH

+

2-chloroaniline

+


→


24528325


Reaction ID UCExp238-37 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.718 M Precipitate Yes but solvent evaporated Comments Reference http://usefulchem.wikispaces.com/Exp238

+

Boc-Gly-OH

+

2-chloroaniline

+


→

t-butyl isocyanide

24528337


+


+

2-chloroaniline

+


→

n-butyl isocyanide

24528368

2-ethylbutyraldehyde Reaction ID UCEXP232-71 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.106 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp232

+

+

+

44

→

Boc-Gly-OH

furfurylamine


t-butyl isocyanide

24528256



+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528257


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528258


+

Boc-Gly-OH

+

furfurylamine

+



45

→


24528259

+

Boc-Gly-OH

+

furfurylamine

+

→



24528260

2-furaldehyde



+


+

furfurylamine

+

2-furaldehyde

→

n-butyl isocyanide

24528187


+

Boc-Gly-OH

+

furfurylamine

+

2-furaldehyde

→

t-butyl isocyanide

24528217


+

Boc-Gly-OH

+

furfurylamine

+

2-furaldehyde


Khalid Mirza Ugi

46

→

n-butyl isocyanide

24528218


+

Boc-Gly-OH

+

furfurylamine

+

2-furaldehyde

→

1-pentyl isocyanide

24528219




+

Boc-Gly-OH

+

furfurylamine

+

2-furaldehyde

→


24528220


+

Boc-Gly-OH

+

furfurylamine

+

→


2-furaldehyde

24528221


+


+

methylamine

+

2-furaldehyde

47

→

benzyl isocyanide

24534403

2-hydroxybenzaldehyde Reaction ID UCEXP171IV2B9 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

aniline

+


→


21106055



+


+

methylamine

+


→

n-butyl isocyanide

21106048

Reaction ID UCEXP174D/V2B35 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+

benzoic acid

+

furfurylamine

+


→


21106202

Reaction ID UCEXP174E/V2B36 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+

Boc-Trp-OH

+

methylamine

+


48

→

n-butyl isocyanide

21106201

Reaction ID UCEXP174Q/V2B50 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+

butyric acid

+

3-chloroaniline

+


→


21106191


Reaction ID UCEXP174R/V2B51 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+

mandelic acid

+

3-chloroaniline

+


→


21106190

Reaction ID UCEXP174T/V2B53 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.219 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+

2,5-dimethoxyphenylacetic acid

+

aniline

+


→


21106185


+


+

1-propylamine

+


49

→


24528102


+


+

1-hexylamine

+


→

t-butyl isocyanide

24528114



+


+

3-chloroaniline

+


→


24528120


+

hexanoic acid

+

3-chloroaniline

+


→


24528122


+

hexanoic acid

+

aniline

+


50

→


24528125


+


+

furfurylamine

+


→


24528128



+

phenylpropynoic acid

+

aniline

+


→


24528137


+


+

aniline

+


→


24528140


+

3-(4methoxyphenyl)propionic acid

+

benzylamine

+


51

→


24528152


+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528222



+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528223


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528224


+

Boc-Gly-OH

+

furfurylamine


+


52

→


24528225


+

Boc-Gly-OH

+

furfurylamine

+

→



24528226

2-hydroxybenzaldehyde Nature Precedings : doi:10.1038/npre.2010.4416.1 : Posted 4 May 2010

Reaction ID UCEXP171EV2B5 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.22 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

3-chloroaniline

+


→


21106047

Reaction ID UCEXP173A/V2B13 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+

4-chlorophenylacetic acid

+

aniline

+


→


21106046


+

+

+

53

→


methylamine



24528098



+


+

furfurylamine

+


→


24528100

2-methoxy-1-naphthaldehyde Reaction ID UCEXP231-8 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.833 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp231

+

glycolic acid

+

1-heptylamine

+


→


24528188

2-methylbenzaldehyde Reaction ID UCEXP181-059V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.225 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+


+

methylamine

+


Reaction ID UCEXP181-070V2 Researcher Reaction Type Solvent


54

→


24528099

Limiting Reactant 0.22 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+


+

3-chloroaniline

+


→

n-butyl isocyanide

24528530



Reaction ID UCEXP225-7 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.879 M Precipitate No Comments 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid Reference http://usefulchem.wikispaces.com/Exp225

+

Boc-Gly-OH

+

furfurylamine

+

→


piperonal

24528163


+


+


+

→


benzaldehyde

24528171


+


+

furfurylamine

+

piperonal

55

→


24528179

2-naphthaldehyde Reaction ID UCEXP130-1 Researcher Rikesh Parikh Reaction Type Ugi Solvent methanol Limiting Reactant 0.751 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp130

+

formic acid

+


+

2-naphthaldehyde

→

n-butyl isocyanide

21106081



+

formic acid

+

1-hexylamine

+

2-naphthaldehyde

→

1-pentyl isocyanide

21106078

Reaction ID UCEXP130-4 Researcher Rikesh Parikh Reaction Type Ugi Solvent methanol Limiting Reactant 0.725 M Precipitate Yes Product Not Determined Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp130

+

formic acid

+

furfurylamine

+

2-naphthaldehyde

→

benzyl isocyanide

21106080


+

+

+

56

→

formic acid

furfurylamine

2-naphthaldehyde

n-butyl isocyanide

21106079


+


+

methylamine

+

2-naphthaldehyde

→

t-butyl isocyanide

21105841


Reaction ID UCEXP171FV2B6 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate Yes but reactants initially insoluble Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

methylamine

+

2-naphthaldehyde

→

t-butyl isocyanide

21105841

Reaction ID UCEXP171GV2B7 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.218 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

furfurylamine

+

2-naphthaldehyde

→


21106054

Reaction ID UCEXP173H/V2B20 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.22 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+

+

+

57

→



2-naphthaldehyde


21106053


+

2,4,6-trihydroxybenzoic acid

+

methylamine

+

2-naphthaldehyde

→


21106188



+


+

aniline

+

2-naphthaldehyde

→


24528108


+


+

2-chloroaniline

+

2-naphthaldehyde

→

t-butyl isocyanide

24528117


+

+

+

58

→


methylamine

2-naphthaldehyde


24528136

Reaction ID UCEXP181-108V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes Product No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181


+

+

D-(−)-Quinic acid

methylamine

+

2-naphthaldehyde

→


24528138


+


+

3-chloroaniline

+

2-naphthaldehyde

→

t-butyl isocyanide

24528144

Reaction ID UCEXP215C Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.662 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp215

+


+

methylamine

+

2-naphthaldehyde


59

→

t-butyl isocyanide

21105841

+

+


+

methylamine

2-naphthaldehyde

→

t-butyl isocyanide

21105841

2-phenylbutyric acid Reaction ID UCEXP174M/V2B45


Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.22 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+

2-phenylbutyric acid

+

3-chloroaniline

+


→


21106194

2-phenylpropionaldehyde Reaction ID UCEXP232-61 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.069 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24534409


+

Boc-Gly-OH

+

furfurylamine

+




60

→

n-butyl isocyanide

24534417


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24534418




+

Boc-Gly-OH

+

furfurylamine

+


→


24534419


+

Boc-Gly-OH

+

furfurylamine

+

→



24534420

2,3-dihydroxybenzoic acid Reaction ID UCEXP147-1V2B1 Researcher Mitesh Shah Reaction Type Ugi Solvent methanol Limiting Reactant 0.659 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp147

+

2,3-dihydroxybenzoic acid

+

methylamine

+

4,7-dimethoxy-1-naphthaldehyde

Reaction ID UCEXP171A/V2B1

61

→


21105839

Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate Yes Product Impurities found Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

methylamine

+


→


21105839


Reaction ID UCEXP173F/V2B18 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.219 M Precipitate no and aldehyde alone not solube Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

furfurylamine

+


→

t-butyl isocyanide

21106041


+


+

methylamine

+


→


24528129


+


+

methylamine

+



Khalid Mirza

62

→


24528141


+


+

+

methylamine

4-chlorobenzaldehyde

→


24528145




+


+

methylamine

+


→

t-butyl isocyanide

21106206


+


+

methylamine

+


→

t-butyl isocyanide

24528291


+


+

t-butylamine

+



63

→

t-butyl isocyanide

24528300


+


+

methylamine

+


→

t-butyl isocyanide

24528361



+


+

methylamine

+


→

n-butyl isocyanide

24528365


+


+

t-butylamine

+


→

t-butyl isocyanide

24528371


+

+

+

64

→


1-propylamine


t-butyl isocyanide

24528375


+



+

3-chloroaniline

+


→

t-butyl isocyanide

24528379


+


+

benzylamine

+


→

t-butyl isocyanide

24528381

2,4-dimethylbenzaldehyde Reaction ID UCEXP228-3 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.551 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp228

+

Boc-Trp-OH

+

octadecylamine

+


2,4,6-trihydroxybenzoic acid Reaction ID UCEXP151-1V2B10 Researcher Mitesh Shah Reaction Type Ugi Solvent methanol Limiting Reactant 0.694 M Precipitate No

65

→

n-butyl isocyanide

24534188

Comments Reference

Protocol from Explan005 followed http://usefulchem.wikispaces.com/Exp151

+


+

methylamine

+


→


21106049

Reaction ID UCEXP171C/V2B3



+


+

methylamine

+


→


21106040

Reaction ID UCEXP171HV2B8 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes Product No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

methylamine

+


→


21105832

Reaction ID UCEXP171JV2B10 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.225 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

methylamine

+


Reaction ID UCEXP174H/V2B40 Researcher Reaction Type Solvent


66

→


21106049


+


+

+

methylamine

2-naphthaldehyde

→


21106188

Reaction ID UCEXP174L/V2B44



+


+

methylamine

+


→


21106195


+


+

furfurylamine

+


→

n-butyl isocyanide

24528097


+


+

methylamine

+


Reaction ID UCEXP181-069V2 Researcher Reaction Type

Khalid Mirza Ugi

67

→


24528105

Solvent methanol Limiting Reactant 0.221 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+


+

+

aniline

2-naphthaldehyde

→


24528108



+


+


+


→

n-butyl isocyanide

24528113


+


+

furfurylamine

+


→

t-butyl isocyanide

24528115

Reaction ID UCEXP181-080V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate Yes Product Not determined Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+


+

aniline


+


68

→


24528116


+


+

methylamine

+


→


24528132



+


+

methylamine

+


→

t-butyl isocyanide

24528534


+


+


+


→

n-butyl isocyanide

24528143

Reaction ID UCEXP181-117V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.22 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed; hydrate of acid used Reference http://usefulchem.wikispaces.com/Exp181

+


+

furfurylamine

+

veratraldehyde

69

→


24534442


+


+

+

3,5Bis(trifluoromethyl)benzaldehyde

methylamine

→


24528149

2,5-dimethoxyphenylacetic acid Nature Precedings : doi:10.1038/npre.2010.4416.1 : Posted 4 May 2010


+


+

aniline

+


→


21106185


+


+

3-chloroaniline

+


2,6-dihydroxybenzoic acid Reaction ID UCEXP181-055V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate no and aldehyde alone not solube Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

70

→


24528120

+


+


+


→

n-butyl isocyanide

24528096



+


+

methylamine

+


→


21106207

3-(4-methoxyphenyl)propionic acid Reaction ID UCEXP155B-V1B159 Researcher Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.674 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp155

+


+

+


benzaldehyde

→

t-butyl isocyanide

21106074


+


+

benzylamine

+


3-chloroaniline 71

→


24528152


+


+

3-chloroaniline

+


→


21106047


Reaction ID UCEXP174M/V2B45 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.22 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+


+

3-chloroaniline

+


→


21106194


+

butyric acid

+

3-chloroaniline

+


→


21106191


+

mandelic acid

+

3-chloroaniline

+


72

→


21106190


+


+

+

3-chloroaniline


→

n-butyl isocyanide

24528530



+


+

3-chloroaniline

+


→


24528120


+

hexanoic acid

+

3-chloroaniline

+


→


24528122


+


+

3-chloroaniline

+

veratraldehyde

73

→


24528142


+


+

+

3-chloroaniline

2-naphthaldehyde

→

t-butyl isocyanide

24528144



+


+

3-chloroaniline

+


→


24528150

Reaction ID UCEXP215G Researcher Khalid Mirza Reaction Type Ugi Solvent THF + methanol Limiting Reactant 0.291 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp215

+

chloroacetic acid

+

+

5-bromo-2thiophenecarboxaldehyde

3-chloroaniline

→

benzyl isocyanide

24528156


+


+

3-chloroaniline

+


74

→

n-butyl isocyanide

24528276


+

formic acid

+

3-chloroaniline

+


→

t-butyl isocyanide

24528281



+

methacrylic acid

+

3-chloroaniline

+


→

n-butyl isocyanide

24528296


+


+

+


3-chloroaniline

→

t-butyl isocyanide

24528298


+

crotonic acid

+

3-chloroaniline

+



75

→


24528304


+

crotonic acid

+

3-chloroaniline

+


→

t-butyl isocyanide

24528316



+

Boc-Gly-OH

+

3-chloroaniline

+


→


24528326


+

Boc-Gly-OH

+

3-chloroaniline

+


→

t-butyl isocyanide

24528338


+


+

3-chloroaniline

+



76

→

t-butyl isocyanide

24528370


+


+

3-chloroaniline

+


→

t-butyl isocyanide

24528379

3-hydroxybenzaldehyde Nature Precedings : doi:10.1038/npre.2010.4416.1 : Posted 4 May 2010

Reaction ID UCEXP173I/V3B21 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.225 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

methylamine

+


→


21106052

Reaction ID UCEXP173L/V2B24 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

furfurylamine

+


→


21106051

Reaction ID UCEXP174N/V2B46 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+

+

+

77

→

Boc-Trp-OH

methylamine


n-butyl isocyanide

21106193



+

+


methylamine

+


→


24528105


+

+


methylamine

+


→


24528121


+


+


+


3-hydroxybenzaldehyde Reaction ID UCEXP228-2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.265 M

78

→


24528533


No Protocol from Explan005 followed http://usefulchem.wikispaces.com/Exp228

+

+

Boc-Trp-OH

octadecylamine

+


→

n-butyl isocyanide

24528182




+

+


methylamine

+


→

t-butyl isocyanide

21106050


+

+


furfurylamine

+


→


21106204

Reaction ID UCEXP174P/V2B49 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.22 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+


+


+



Khalid Mirza

79

→


21106192

Reaction Type Ugi Solvent methanol Limiting Reactant 0.225 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+


+


+


→

n-butyl isocyanide

24528113



+


+

aniline

+


→


24528116


+

mandelic acid

+

benzylamine

+


→

n-butyl isocyanide

24528119


+

decanoic acid

+

2-chloroaniline

+



80

→


24528124


+


+

methylamine

+


→


24528127



+


+

1-hexylamine

+


→


24528139

3-methylbut-2-enoic acid Reaction ID UCEXP181-064V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+


+

1-hexylamine

+


→


24528103

3,3'-dichloropivalic acid Reaction ID UCExp236-01 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.614 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp236

+

+

+

81

→


t-butylamine


n-butyl isocyanide

24528275



+


+

3-chloroaniline

+


→

n-butyl isocyanide

24528276


+


+

benzylamine

+


→

n-butyl isocyanide

24528277

Reaction ID UCExp236-07 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.614 M Precipitate Yes Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp236

+


+

1-hexylamine

+



82

→

t-butyl isocyanide

24528280

+


+

2-chloroaniline

+


→

t-butyl isocyanide

24528282



+


+

1-propylamine

+


→

n-butyl isocyanide

24528286


+


+

+


methylamine

→

t-butyl isocyanide

24528287


+


+

1-heptylamine

+



83

→

t-butyl isocyanide

24528288

+

+


aniline

+


→

n-butyl isocyanide

24528290



+


+

methylamine

+


→

t-butyl isocyanide

24528291


+


+

+


t-butylamine

→

t-butyl isocyanide

24528295


+


+

3-chloroaniline

+



84

→

t-butyl isocyanide

24528298

+


+

+


benzylamine

→

t-butyl isocyanide

24528299



+


+

t-butylamine

+


→

t-butyl isocyanide

24528300


+


+

cyclohexylamine

+


→

t-butyl isocyanide

24528302

3,4-dihydroxybenzaldehyde Reaction ID UCEXP151-1V2B10 Researcher Mitesh Shah Reaction Type Ugi Solvent methanol Limiting Reactant 0.694 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp151

+


+

methylamine

+


Reaction ID UCEXP171JV2B10 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.225 M

85

→


21106049



+


+

methylamine

+


→


21106049

Reaction ID UCEXP173E/V2B17



+

Boc-Trp-OH

+

methylamine

+


→

t-butyl isocyanide

21106045


+


+

methylamine

+


→

t-butyl isocyanide

21106038


+

methacrylic acid

+

aniline

+


Reaction ID UCEXP174M/V2B45 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.22 M Precipitate No

86

→


21106198

Comments Reference


+


+

3-chloroaniline

+


→


21106194




+


+

1-hexylamine

+


→


24528103


+


+

aniline

+


→

t-butyl isocyanide

24528110


+

diphenylacetic acid

+

1-propylamine

+


Reaction ID UCEXP181-082V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed

87

→

n-butyl isocyanide

24528112

Reference


+


+

furfurylamine

+


→


24528118




+

diphenylacetic acid

+


+


→

n-butyl isocyanide

24528532


+

4-nitrobenzoic acid

+

methylamine

+


→


24528123


+


+

t-butylamine

+



88

→


24528135

+

+

diphenylacetic acid

methylamine

+


→

n-butyl isocyanide

24528148



+

+


3-chloroaniline

+


→


24528150

3,4-dihydroxyphenyl acetic acid Reaction ID UCEXP174J/V2B42 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+

3,4-dihydroxyphenyl acetic acid

+

+



→


21106197

3,4-dihydroxyphenylacetic acid Reaction ID UCEXP160C-V1B19 Researcher Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.388 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp160

+


+

furfurylamine

+


Reaction ID UCEXP171GV2B7 Researcher

Khalid Mirza

89

→

n-butyl isocyanide

21105579


+


+

+

furfurylamine

2-naphthaldehyde

→


21106054



+


+

+


2-naphthaldehyde

→


21106053


+


+

methylamine

+


→


21106052


+


+

furfurylamine

+


Reaction ID UCEXP173M/V2B25

90

→


21106051


+


+

furfurylamine

+


→


21106043


Reaction ID UCEXP173O/V2B27 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate Yes Product pending Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

furfurylamine

+

benzaldehyde

→


21105843


+


+

furfurylamine

+


→


21106042


+


+


+

benzaldehyde

91

→


21106189


+


+

furfurylamine

+


→


21106204


Reaction ID UCEXP174F/V2B38 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+


+

methylamine

+

veratraldehyde

→


21106200

Reaction ID UCEXP174G/V2B39 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+


+

1-propylamine

+


→


21106199


+

+

+

3,4-dihydroxyphenylacetic

92

→


acid



21106192

Reaction ID UCEXP174U/V2B54 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.22 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+


+

furfurylamine

+


→


21106187



+


+

1-propylamine

+


→


24528102


+


+

furfurylamine

+


→


24528106


+

+

+

93

→


methylamine

o-vanillin


24528107



+


+

aniline

+


→

t-butyl isocyanide

24528110


+


+

+

2-chloroaniline

2-naphthaldehyde

→

t-butyl isocyanide

24528117


+


+

furfurylamine

+



94

→


24528118

Reference


+

+


furfurylamine

+


→


24528126




+

+


furfurylamine

+


→


24528128


+


+


+


→


24528533


+


+

aniline

+


Reaction ID UCEXP181-113V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.219 M Precipitate No

95

→


24528140

Comments Reference


+


+

+

3-chloroaniline

veratraldehyde

→


24528142




+


+

+

3-chloroaniline

2-naphthaldehyde

→

t-butyl isocyanide

24528144


+


+

+


methylamine

→


24528147

Reaction ID UCEXP181-123V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.214 M Precipitate no and aldehyde alone not solube Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+


+

furfurylamine

+


3,4-methylenedioxyphenylacetic acid Reaction ID UCEXP167A-V1B12

96

→


24528151

Researcher Tim Bohinsky Reaction Type Ugi Solvent methanol Limiting Reactant 0.403 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp167

+


+

1-propylamine

+


→

n-butyl isocyanide

21105597



+


+

3-chloroaniline

+


→


21106047

Reaction ID UCEXP171IV2B9 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

aniline

+


→


21106055


+

+

+

97

→


methylamine


benzyl isocyanide

24534407


+



+

methylamine

+

m-anisaldehyde

→

benzyl isocyanide

24534408


+


+

methylamine

+

2-furaldehyde

→

benzyl isocyanide

24534403


+


+

methylamine

+

veratraldehyde


98

→

n-butyl isocyanide

24528355

+


+

methylamine

+

veratraldehyde

→

n-butyl isocyanide

24528355




+


+

methylamine

+

veratraldehyde

→

t-butyl isocyanide

24528356


+


+

methylamine

+

veratraldehyde

→

t-butyl isocyanide

24528356

Reaction ID UCExp241-08 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.52 M Precipitate YES Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp241

+


+

methylamine

+

veratraldehyde


Khalid Mirza

99

→


21782465

Reaction Type Ugi Solvent methanol Limiting Reactant 0.564 M Precipitate YES Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp241

+


+

methylamine

+

veratraldehyde

→


21782465



+


+

methylamine

+

→


veratraldehyde

24528357


+


+

methylamine

+

→


veratraldehyde

24528357


+

+

+

100

→


methylamine

veratraldehyde

1-pentyl isocyanide

24528358




+


+

methylamine

+

veratraldehyde

→

1-pentyl isocyanide

24528358


+


+

methylamine

+

veratraldehyde

→

benzyl isocyanide

24528359


+


+

methylamine

+

veratraldehyde


Khalid Mirza Ugi

101

→

benzyl isocyanide

24528359


+


+

+

methylamine

veratraldehyde

→

benzyl isocyanide

24528359



+


+

+


methylamine

→

t-butyl isocyanide

24528360


+


+

methylamine

+


→

t-butyl isocyanide

24528361


+


+

methylamine

+


102

→

t-butyl isocyanide

24528362


+


+

+

methylamine

o-tolualdehyde

→

t-butyl isocyanide

24528363



+


+

+


methylamine

→

n-butyl isocyanide

24528364


+


+

methylamine

+


→

n-butyl isocyanide

24528365


+

+

+

103

→


1-hexylamine


n-butyl isocyanide

24528366




+


+

+


butylamine

→

t-butyl isocyanide

24528367


+


+

2-chloroaniline

+


→

n-butyl isocyanide

24528368


+


+

aniline

+



Khalid Mirza Ugi

104

→

n-butyl isocyanide

24528369


+


+

+


3-chloroaniline

→

t-butyl isocyanide

24528370



+


+

t-butylamine

+


→

t-butyl isocyanide

24528371


+


+

cyclohexylamine

+


→

t-butyl isocyanide

24528373


+


+

aniline

+


105

→

t-butyl isocyanide

24528374


+


+

1-propylamine

+


→

t-butyl isocyanide

24528375



+


+

furfurylamine

+


→

t-butyl isocyanide

24528376


+


+

1-heptylamine

+


→

n-butyl isocyanide

24528377


+

+

+

106

→



t-butylamine

t-butyl isocyanide

24528378




+


+

3-chloroaniline

+


→

t-butyl isocyanide

24528379


+


+

1-heptylamine

+


→

t-butyl isocyanide

24528380


+


+

benzylamine

+



Khalid Mirza Ugi

107

→

t-butyl isocyanide

24528381


+


+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528391



+


+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528391


+


+


+

piperonal

→

n-butyl isocyanide

24528392


+


+


+

piperonal

108

→

n-butyl isocyanide

24528392


+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528393



+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528393


+


+

furfurylamine

+

piperonal

→


24528394


+

+

+

109

→


furfurylamine

piperonal


24528394




+

+


furfurylamine

+

→


piperonal

24528395


+

+


furfurylamine

+

→


piperonal

24528395


+


+


+

piperonal


Khalid Mirza Ugi

110

→

t-butyl isocyanide

24528396


+


+


+

piperonal

→

t-butyl isocyanide

24528396



+


+


+

piperonal

→


24528397


+


+


+

piperonal

→


24528397


+


+


+

piperonal

111

→


24528398


+


+


+

→


piperonal

24528398



+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528407


+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528407


+

+

+

112

→


furfurylamine


piperonal

24528408




+


+

furfurylamine

+

→


piperonal

24528408


+


+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528409


+


+

furfurylamine

+

piperonal


Khalid Mirza Ugi

113

→

n-butyl isocyanide

24528409


+


+

+


piperonal

→

n-butyl isocyanide

24528410



+


+

+


piperonal

→

n-butyl isocyanide

24528410

3,5-Bis(trifluoromethyl)benzaldehyde Reaction ID UCEXP181-120V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+


+

+


methylamine

→


24528149


+

+

+

114

→



benzylamine

t-butyl isocyanide

24528266

Reaction ID UCEXP234-2 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 1.002 M Precipitate Yes Product Pending Comments Reference http://usefulchem.wikispaces.com/Exp234

+



+

+


benzylamine

→


23078614


+


+

+


benzylamine

→

t-butyl isocyanide

24528266


+


+

benzylamine

+


3,5-dimethoxybenzaldehyde Reaction ID UCEXP171HV2B8 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes Product No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

115

→


23078614

+


+

methylamine

+


→


21105832

Reaction ID UCEXP173G/V2B19


Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

benzylamine

+


→

n-butyl isocyanide

21105845

Reaction ID UCEXP174O/V2B47 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+

D-(−)-Quinic acid

+


+


→

t-butyl isocyanide

21106186


+


+

methylamine

+



116

→


24528101

+

D-(−)-Quinic acid

+

benzylamine

+


→

t-butyl isocyanide

24528104



+


+

furfurylamine

+


→


24528126


+


+

benzylamine

+


→

t-butyl isocyanide

24534439


+


+

benzylamine

+


Reaction ID UCEXP233-11 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 1.021 M Precipitate No Comments -

117

→


23078615

Reference


+

Boc-Pro-OH

+

benzylamine

+


→

t-butyl isocyanide

24528262



+

Boc-Pro-OH

+

benzylamine

+


→


24528263


+


+

benzylamine

+


→


24534440


+


+

benzylamine

+


Reaction ID UCEXP233-4 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 0.917 M Precipitate Yes Product Pending Comments -

118

→

t-butyl isocyanide

24528265

Reference


+


+

benzylamine

+


→


23078615



+

Boc-Pro-OH

+

benzylamine

+


→

t-butyl isocyanide

24528262


+

Boc-Pro-OH

+

benzylamine

+


→


24528263


+


+

benzylamine

+



119

→

t-butyl isocyanide

24534439

+


+

benzylamine

+


→


24534440



+


+

benzylamine

+


→

t-butyl isocyanide

24528265

Reaction ID UCEXP234-10 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 0.916 M Precipitate Reactants insoluble Comments Reference http://usefulchem.wikispaces.com/Exp234

+

Boc-L-Serine

+

benzylamine

+


→


24528267


+

Boc-L-Threonine

+

glycine methyl ester hydrochloride

+



120

→

t-butyl isocyanide

24528268

+

+


Boc-L-Threonine

+


→


24528269



+

Fmoc-Diglycine

+

benzylamine

+


→

t-butyl isocyanide

24528270


+

Fmoc-Diglycine

+

benzylamine

+


→


24528271


+

Boc-diglycine

+

benzylamine

+



121

→

t-butyl isocyanide

24528272

+

+

Boc-diglycine

benzylamine

+


→


24528273



+

+

Boc-L-Serine

benzylamine

+


→

t-butyl isocyanide

24528274

4-(dimethylamino)benzaldehyde Reaction ID UCEXP171KV2B11 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate Yes Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

methylamine

+


→

t-butyl isocyanide

21105842


+

D-(−)-Quinic acid

+

methylamine

+


Reaction ID UCEXP215D Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.66 M Precipitate No

122

→


24528134

Comments Reference


+

+


methylamine

+


→

t-butyl isocyanide

21105842




+

+


methylamine

+


→

t-butyl isocyanide

21105842

Reaction ID UCEXP228-5 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.372 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp228

+

Boc-Trp-OH

+


+


→


24534191

4-(trifluoromethyl)benzaldehyde Reaction ID UCEXP173C/V2B15 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

methylamine

+


Reaction ID UCEXP181-072V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.224 M

123

→

t-butyl isocyanide

21106044



+

+


methylamine

+


→


21106207




+

methacrylic acid

+


+


→

t-butyl isocyanide

21111670


+

+

methacrylic acid

benzylamine

+


→

t-butyl isocyanide

21111671


+

methacrylic acid

+


+


Reaction ID UCEXP187-2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.06 M Precipitate Yes Yield - %

124

→

t-butyl isocyanide

21111670

Comments Reference


+

methacrylic acid

+

benzylamine

+


→

t-butyl isocyanide

21111671




+

methacrylic acid

+

t-butylamine

+


→

t-butyl isocyanide

21143155


+

methacrylic acid

+


+


→

t-butyl isocyanide

21111670


+

methacrylic acid

+

benzylamine

+



125

→

t-butyl isocyanide

21111671

+

+

methacrylic acid

t-butylamine

+


→

t-butyl isocyanide

21143155



+

Boc-Trp-OH

+


+


→

n-butyl isocyanide

24534190

Reaction ID UCEXP231-4 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 2 M Precipitate Yes Product Pending Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp231

+

methoxy acetic ac id

+


+


→

n-butyl isocyanide

21486238


+

Boc-Gly-OH

+

furfurylamine

+


Reaction ID UCEXP232-12 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.028 M Precipitate Yes Product Pending Comments -

126

→

t-butyl isocyanide

24528198

Reference


+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528199



Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.029 M Precipitate Yes Product Pending Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528200


+

Boc-Gly-OH

+

furfurylamine

+


→


21782441


+

Boc-Gly-OH

+

furfurylamine

+


Reaction ID UCExp235-1 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1 M

127

→


24528201

Precipitate Product Comments Reference

Yes No http://usefulchem.wikispaces.com/Exp235

+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528198



Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1 M Precipitate Yes Product No Comments Reference http://usefulchem.wikispaces.com/Exp235

+

Boc-Gly-OH

+

furfurylamine

+


→


21782441


+


+

t-butylamine

+


→

n-butyl isocyanide

24528275


+


+

3-chloroaniline

+



128

→

n-butyl isocyanide

24528276



+


+

benzylamine

+


→

n-butyl isocyanide

24528277




+

methacrylic acid

+

butylamine

+


→

t-butyl isocyanide

24528278


+

formic acid

+

t-butylamine

+


→

t-butyl isocyanide

24528279


+


+

1-hexylamine

+


Reaction ID UCExp236-08 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.65 M Precipitate No

129

→

t-butyl isocyanide

24528280

Comments Reference


+

formic acid

+

3-chloroaniline

+


→

t-butyl isocyanide

24528281




+


+

2-chloroaniline

+


→

t-butyl isocyanide

24528282


+

methacrylic acid

+

methylamine

+


→

n-butyl isocyanide

24528283


+

formic acid

+

benzylamine

+



130

→

t-butyl isocyanide

24528284

+

+

methacrylic acid

aniline

+


→

t-butyl isocyanide

24528285



+


+

1-propylamine

+


→

n-butyl isocyanide

24528286


+


+

1-heptylamine

+


→

t-butyl isocyanide

24528288


+

formic acid

+

butylamine

+



131

→

t-butyl isocyanide

24528289

+

+


aniline

+


→

n-butyl isocyanide

24528290



+

formic acid

+

methylamine

+


→

n-butyl isocyanide

24528292


+

methacrylic acid

+

t-butylamine

+


→

n-butyl isocyanide

24528293


+

formic acid

+

aniline

+



132

→

t-butyl isocyanide

24528294

+

methacrylic acid

+

3-chloroaniline

+


→

n-butyl isocyanide

24528296



+

methacrylic acid

+

benzylamine

+


→

n-butyl isocyanide

24528297


+

methacrylic acid

+

1-hexylamine

+


→

t-butyl isocyanide

24528301


+


+

cyclohexylamine

+



133

→

t-butyl isocyanide

24528302

+


+

1-hexylamine

+


→

n-butyl isocyanide

24528366




+


+

2-chloroaniline

+


→

n-butyl isocyanide

24528368


+

+


aniline

+


→

n-butyl isocyanide

24528369


+


+

cyclohexylamine

+



Khalid Mirza Ugi

134

→

t-butyl isocyanide

24528373


+


+

furfurylamine

+


→

t-butyl isocyanide

24528376



+


+

1-heptylamine

+


→

n-butyl isocyanide

24528377


+


+

1-heptylamine

+


→

t-butyl isocyanide

24528380

4-chlorobenzaldehyde Reaction ID UCEXP158B-V1B16 Researcher Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.658 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp158

+

+

+

135

→

salicylic acid




21106076



+


+

furfurylamine

+


→


21106043

Reaction ID UCEXP174J/V2B42 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+


+


+


→


21106197


+

D-(−)-Quinic acid

+

methylamine

+



136

→


24528131

+


+

+

methylamine


→


24528145

4-chlorophenylacetic acid Reaction ID UCEXP159C-V1B18


Researcher Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.661 M Precipitate Yes but the aldehyde alone is not soluble in methanol Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp159

+


+

benzylamine

+


→

n-butyl isocyanide

21106077


+


+

aniline

+


→


21106046

Reaction ID UCEXP175D Researcher Khalid Mirza/ Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.398 M Precipitate Yes but the aldehyde alone is not soluble in methanol Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp175

+


+

benzylamine

+


Reaction ID UCEXP179 Researcher Shannon Oseback Reaction Type Ugi Solvent methanol Limiting Reactant 0.286 M Precipitate Reactants Insoluble

137

→

n-butyl isocyanide

21106077

Comments Reference


+

+


aniline

+


→

t-butyl isocyanide

21105833




+

+


t-butylamine

+


→


24528135


+


+

3-chloroaniline

+


→


24528150

Reaction ID UCEXP215E Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.715 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp215

+


+

methylamine

+


Reaction ID UCEXP215F Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.661 M Precipitate Yes but not at room temperature Yield - % Comments -

138

→

t-butyl isocyanide

24528155

Reference


+


+

benzylamine

+


→

n-butyl isocyanide

21106077



+


+

benzylamine

+


→

n-butyl isocyanide

21106077

4-hydroxybenzaldehyde Reaction ID UCEXP181-067V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+


+

furfurylamine

+


→


24528106


+


+

methylamine

+


4-hydroxybenzoic acid Reaction ID UCEXP181-059V2 Researcher

Khalid Mirza

139

→


24528129


+


+

+

methylamine


→


24528099



+


+

methylamine

+


→


24528101


+


+

methylamine

+


→


24528121


+


+

methylamine

+


Reaction ID UCEXP181-099V2 Researcher Reaction Type Solvent


140

→


24528127


+


+

2-chloroaniline

+


→


24528130




+


+

+

methylamine

2-naphthaldehyde

→


24528136


+


+

1-hexylamine

+


→


24528139


+


+

2-chloroaniline

+

veratraldehyde

4-methoxybenzaldehyde Reaction ID UCEXP174L/V2B44 Researcher Reaction Type

Khalid Mirza Ugi

141

→


24534443

Solvent methanol Limiting Reactant 0.224 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+


+

methylamine

+


→


21106195



+


+

furfurylamine

+


→


21106187


+


+

2-chloroaniline

+


→


24528130


+


+

methylamine

+



Khalid Mirza Ugi

142

→


24528141

Solvent methanol Limiting Reactant 1.066 M Precipitate Yes Product Pending Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528232



+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528233


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528234


+

Boc-Gly-OH

+

furfurylamine

+



Khalid Mirza Ugi

143

→


24528235


+

Boc-Gly-OH

+

furfurylamine

+

→



24528236



+


+

methylamine

+


→

benzyl isocyanide

24534407

4-methylbenzaldehyde Reaction ID UCEXP173B/V2B14 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes but reactants initially insoluble Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

methylamine

+


→

t-butyl isocyanide

21105844


+

+

+

144

→


furfurylamine



21106042


+


+

1-propylamine

+


→


21106199



+


+

methylamine

+


→

t-butyl isocyanide

24528155


+


+

methylamine

+


→

t-butyl isocyanide

21105844


+

+

+

145

→


methylamine


t-butyl isocyanide

21105844


+

Boc-Trp-OH

+

octadecylamine

+


→

t-butyl isocyanide

24534189


Reaction ID UCEXP231-1 Researcher Khalid Mirza Reaction Type Ugi Solvent acetonitrile Limiting Reactant 1.538 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp231

+

formic acid

+

benzylamine

+


→


24528186


+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528193


+

Boc-Gly-OH

+

furfurylamine

+


146

→

n-butyl isocyanide

24528194


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528195



+

Boc-Gly-OH

+

furfurylamine

+


→


24528196


+

Boc-Gly-OH

+

furfurylamine

+

→



24528197


+

+

+

147

→


methylamine


t-butyl isocyanide

24528362

4-nitrobenzoic acid Reaction ID UCEXP181-090V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.226 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181


+

4-nitrobenzoic acid

+

+

methylamine


→


24528123

4,7-dimethoxy-1-naphthaldehyde Reaction ID UCEXP147-1V2B1 Researcher Mitesh Shah Reaction Type Ugi Solvent methanol Limiting Reactant 0.659 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp147

+


+

methylamine

+


→


21105839

Reaction ID UCEXP171A/V2B1 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate Yes Product Impurities found Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

methylamine

+


Reaction ID UCEXP174S/V2B52 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.225 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

148

→


21105839

+

+

5-nitrosalicylic acid

methylamine

+


→

n-butyl isocyanide

21106203



+

+


methylamine

+


→


24528132


+

Boc-Trp-OH

+

octadecylamine

+


→


24528181

5-(trifluoromethyl)-2-furylmethylamine Reaction ID UCEXP109C Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate Yes Product Pending Comments Imine was preformed Reference http://usefulchem.wikispaces.com/Exp109

+

Boc-Gly-OH

+

5-(trifluoromethyl)-2furylmethylamine

+

benzaldehyde

5-bromo-2-thiophenecarboxaldehyde Reaction ID UCEXP181-118V2

149

→

benzyl isocyanide

21105565


+


+

+


methylamine

→


24528147



+

chloroacetic acid

+

+


3-chloroaniline

→

benzyl isocyanide

24528156


+


+

+


methylamine

→

t-butyl isocyanide

24528287


+


+

t-butylamine

+


150

→

t-butyl isocyanide

24528295


+


+

+


3-chloroaniline

→

t-butyl isocyanide

24528298



+


+

+


benzylamine

→

t-butyl isocyanide

24528299


+


+

+


methylamine

→

t-butyl isocyanide

24528360


+

3,4-

+

+

151

→

methylenedioxyphenylacetic acid


methylamine

n-butyl isocyanide

24528364


+



+

+


butylamine

→

t-butyl isocyanide

24528367


+


+

+


3-chloroaniline

→

t-butyl isocyanide

24528370


+


+

aniline

+



152

→

t-butyl isocyanide

24528374

+

+


+


t-butylamine

→

t-butyl isocyanide

24528378



Reaction ID UCEXP052E Researcher Alicia Holsey Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes Yield 32 % Comments 1M solutions of the starting materials was made Reference http://usefulchem.wikispaces.com/Exp052

+

Boc-Gly-OH

+


+

piperonal

→

t-butyl isocyanide

10481872

Reaction ID UCEXP064C Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.393 M Precipitate Yes Yield 43.8 % Comments Solution was made up to 4 mL - methanol amount probably closer to 3 mL Reference http://usefulchem.wikispaces.com/Exp064

+

Boc-Gly-OH

+


+

veratraldehyde

→

benzyl isocyanide

10481870

Reaction ID UCEXP086B Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.402 M Precipitate Yes Yield 38 % Comments Solution was made up to 4 mL - methanol amount probably closer to 3 mL Reference http://usefulchem.wikispaces.com/Exp086

+

Boc-Gly-OH

+


+

benzaldehyde

153

→

t-butyl isocyanide

10481766


+

formic acid

+


+

2-naphthaldehyde

→

n-butyl isocyanide

21106081



+

formic acid

+


+

benzaldehyde

→


21106060


+

Boc-Trp-OH

+


+

veratraldehyde

→

1-pentyl isocyanide

21106069

Reaction ID UCEXP155B-V1B159 Researcher Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.674 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp155

+


+


+

benzaldehyde

154

→

t-butyl isocyanide

21106074


+

salicylic acid

+


+


→


21106076



+


+


+

o-vanillin

→

t-butyl isocyanide

21106056


+


+


+

2-naphthaldehyde

→


21106053


+


+


+

benzaldehyde

155

→


21106189


+


+

+



→


21106197



+

D-(−)-Quinic acid

+


+


→

t-butyl isocyanide

21106186


+


+


+


→


21106192


+


+


+


156

→

n-butyl isocyanide

24528096


+


+


+


→

n-butyl isocyanide

24528113



+

diphenylacetic acid

+


+


→

n-butyl isocyanide

24528532


+


+


+


→


24528533


+


+


+


157

→

n-butyl isocyanide

24528143


+

methacrylic acid

+


+


→

t-butyl isocyanide

21111670



+

methacrylic acid

+


+


→

t-butyl isocyanide

21111670


+

methacrylic acid

+


+


→

t-butyl isocyanide

21111670


+


+


+

benzaldehyde


158

→

t-butyl isocyanide

24528165


+


+


+

benzaldehyde

→

n-butyl isocyanide

24528166



+


+


+

benzaldehyde

→

1-pentyl isocyanide

24528167


+


+


+

benzaldehyde

→


24528168


+


+


+

benzaldehyde


David Bulger Ugi

159

→

benzyl isocyanide

24528169

Solvent THF Limiting Reactant 0.501 M Precipitate No Comments 0.5 mmol of isocyanide was added to 900uL of a 0.55M solution of aldehyde; amine and acid Reference http://usefulchem.wikispaces.com/Exp226

+


+

+


benzaldehyde

→


24528170




+


+

+


→


benzaldehyde

24528171


+


+

+


→


benzaldehyde

24528172


+

Boc-Trp-OH

+


+


Reaction ID UCEXP228-6 Researcher

Khalid Mirza

160

→


24534191


+

Boc-Trp-OH

+


+


→

n-butyl isocyanide

24534190



+


+


+


→

n-butyl isocyanide

21486238


+

phenylacetic acid

+


+


→

n-butyl isocyanide

21782451


+

phenylacetic acid

+


+



Khalid Mirza

161

→

t-butyl isocyanide

24528348

Reaction Type Ugi Solvent THF Limiting Reactant 1.78 M Precipitate Yes Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp240

+

phenylacetic acid

+


+


→


21782450



+

phenylacetic acid

+


+

→



24528349


+

phenylacetic acid

+


+


→

benzyl isocyanide

24528350


+

phenylacetic acid

+


+


162

→

1-pentyl isocyanide

24528351


+

phenylacetic acid

+


+


→

1-pentyl isocyanide

24528382



+

phenylacetic acid

+


+


→

n-butyl isocyanide

24528387


+

phenylacetic acid

+


+


→

t-butyl isocyanide

24528388


+

phenylacetic acid

+


+



163

→


24528389


+

phenylacetic acid

+


+

→



24528390



+


+


+

piperonal

→

n-butyl isocyanide

24528392


+


+


+

piperonal

→

n-butyl isocyanide

24528392


+

3,4-

+

+

164

→

methylenedioxyphenylacetic acid


piperonal

t-butyl isocyanide

24528396


+



+


+

piperonal

→

t-butyl isocyanide

24528396


+


+


+

piperonal

→


24528397


+


+


+

piperonal


165

→


24528397

+


+


+

→


piperonal

24528398




+


+


+

→


piperonal

24528398


+

cbz-proline

+


+

piperonal

→

n-butyl isocyanide

24528400


+

cbz-proline

+


+

piperonal

Reaction ID UCExp245-27 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.494 M Precipitate No Comments -

166

→

n-butyl isocyanide

24528400

Reference


+

cbz-proline

+


+

piperonal

→

t-butyl isocyanide

24528404



+

cbz-proline

+


+

piperonal

→

t-butyl isocyanide

24528404


+

cbz-proline

+


+

→


piperonal

24528405


+

cbz-proline

+


+

piperonal


167

→


24528405

Comments Reference


+

cbz-proline

+


+

piperonal

→


24528406




+

cbz-proline

+


+

piperonal

→


24528406


+


+


+

piperonal

→

n-butyl isocyanide

24528410


+


+


+

piperonal

5-nitrosalicylic acid Reaction ID UCEXP174C/V2B34

168

→

n-butyl isocyanide

24528410

Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.226 M Precipitate Yes but the aldehyde alone is not soluble in methanol Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+


+

methylamine

+


→

n-butyl isocyanide

21106205



+


+

methylamine

+


→

n-butyl isocyanide

21106203

acetic acid Reaction ID UCEXP180 Researcher Shannon Oseback Reaction Type Ugi Solvent methanol Limiting Reactant 0.403 M Precipitate no and aldehyde alone not solube Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp180

+

acetic acid

+

1-heptylamine

+


→

n-butyl isocyanide

21105834

aniline Reaction ID UCEXP164 Researcher Emily Messner/Shannon Oseback Reaction Type Ugi Solvent methanol Limiting Reactant 0.287 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp164

+

+

+

169

→

phenylacetic acid

aniline


n-butyl isocyanide

21106183



+


+

aniline

+


→


21106055


+


+

aniline

+


→


21106046


+

methacrylic acid

+

aniline

+



170

→


21106198

+


+

aniline

+


→


21106185

Reaction ID UCEXP179 Researcher Shannon Oseback Reaction Type Ugi Solvent methanol Limiting Reactant 0.286 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp179


+


+

aniline

+


→

t-butyl isocyanide

21105833


+


+

+

aniline

2-naphthaldehyde

→


24528108


+


+

aniline

+


Reaction ID UCEXP181-080V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate Yes Product Not determined Comments Protocol from Explan005 followed

171

→

t-butyl isocyanide

24528110

Reference


+


+

aniline

+


→


24528116




+


+

+

aniline

benzaldehyde

→

n-butyl isocyanide

21106208


+

hexanoic acid

+

aniline

+


→


24528125


+


+

aniline

+



172

→


24528137

+


+

aniline

+


→


24528140



+

methacrylic acid

+

aniline

+


→

t-butyl isocyanide

24528285


+


+

aniline

+


→

n-butyl isocyanide

24528290


+

formic acid

+

aniline

+



173

→

t-butyl isocyanide

24528294

+

crotonic acid

+

aniline

+


→


24528305



+

crotonic acid

+

aniline

+


→

t-butyl isocyanide

24528317


+

Boc-Gly-OH

+

aniline

+


→


24528327


+

Boc-Gly-OH

+

aniline

+



174

→

t-butyl isocyanide

24528339

+

+


aniline

+


→

n-butyl isocyanide

24528369




+

+


+


aniline

→

t-butyl isocyanide

24528374

benzaldehyde Reaction ID UCEXP086B Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.402 M Precipitate Yes Yield 38 % Comments Solution was made up to 4 mL - methanol amount probably closer to 3 mL Reference http://usefulchem.wikispaces.com/Exp086

+

Boc-Gly-OH

+


+

benzaldehyde

→

t-butyl isocyanide

10481766


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP108C Researcher

Khalid Mirza

175

→

t-butyl isocyanide

21106059

Reaction Type Ugi Solvent methanol Limiting Reactant 0.393 M Precipitate Yes Yield 20.4 % Comments Imine was preformed Reference http://usefulchem.wikispaces.com/Exp108

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

benzyl isocyanide

21106009


Reaction ID UCEXP109C Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate Yes Product Pending Comments Imine was preformed Reference http://usefulchem.wikispaces.com/Exp109

+

+


Boc-Gly-OH

+

benzaldehyde

→

benzyl isocyanide

21105565


+

formic acid

+


+

benzaldehyde

→


21106060


+


+


+

benzaldehyde

176

→

t-butyl isocyanide

21106074


+


+

furfurylamine

+

benzaldehyde

→


21105843



+


+


+

benzaldehyde

→


21106189


+

mandelic acid

+

benzylamine

+

benzaldehyde

→


24528531


+

+

+

177

→

Boc-Trp-OH

methylamine

benzaldehyde

t-butyl isocyanide

24528109



+

+


aniline

+

benzaldehyde

→

n-butyl isocyanide

21106208

Reaction ID UCEXP201-01 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.039 M Precipitate Yes Yield 50.73 % Comments Automated liquid handling Reference http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP201-03 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.018 M Precipitate Yes Yield 61.55 % Comments Automated liquid handling

178

→

t-butyl isocyanide

21106059

Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.007 M Precipitate Yes Yield 60.31 % Comments Automated liquid handling Reference http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP201-07 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.289 M Precipitate Yes

179

→

t-butyl isocyanide

21106059

Yield Comments Reference

52.42 % Automated liquid handling http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059




+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde



180

→

t-butyl isocyanide

21106059

Limiting Reactant 0.287 M Precipitate Yes Yield 53.43 % Comments Automated liquid handling Reference http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

181

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

182

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059

Reaction ID UCEXP201-19 Researcher Khalid Mirza Reaction Type Ugi Solvent ethanol Limiting Reactant 0.289 M Precipitate Yes Yield 51.52 % Comments Automated liquid handling Reference http://usefulchem.wikispaces.com/Exp201


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP201-22 Researcher Khalid Mirza Reaction Type Ugi Solvent ethanol Limiting Reactant 0.286 M Precipitate Yes Yield 54.11 %

183

→

t-butyl isocyanide

21106059

Comments Reference

Automated liquid handling http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



Researcher Khalid Mirza Reaction Type Ugi Solvent ethanol Limiting Reactant 0.287 M Precipitate Yes Yield 55.91 % Comments Automated liquid handling Reference http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP201-26 Researcher Khalid Mirza Reaction Type Ugi Solvent ethanol Limiting Reactant 0.074 M

184

→

t-butyl isocyanide

21106059

Precipitate Yield Comments Reference

Yes 2.25 % Automated liquid handling http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

185

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


Reaction ID UCEXP201-31 Researcher Khalid Mirza Reaction Type Ugi Solvent acetonitrile Limiting Reactant 0.289 M Precipitate Yes Yield 39.23 % Comments Automated liquid handling Reference http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

186

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP201-37 Researcher Khalid Mirza Reaction Type Ugi Solvent acetonitrile Limiting Reactant 0.074 M Precipitate Yes Yield 0.68 %

187

→

t-butyl isocyanide

21106059

Comments Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



Researcher Khalid Mirza Reaction Type Ugi Solvent acetonitrile Limiting Reactant 0.074 M Precipitate Yes Yield 1.8 % Comments Automated liquid handling Reference http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP201-41 Researcher Khalid Mirza Reaction Type Ugi Solvent acetonitrile Limiting Reactant 0.074 M

188

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059

Reaction ID UCEXP201-43 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.289 M Precipitate Yes Yield 6.54 % Comments Automated liquid handling Reference http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

189

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

190

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059

Reaction ID UCEXP217-3 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.383 M Precipitate Yes Product Pending Comments Reference http://usefulchem.wikispaces.com/Exp217


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059

Reaction ID UCEXP217-4 Researcher Khalid Mirza Reaction Type Ugi Solvent DMSO Limiting Reactant 0.383 M Precipitate Yes Product Pending Comments Reference http://usefulchem.wikispaces.com/Exp217

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059

Reaction ID UCEXP222-1 Researcher Khalid Mirza Reaction Type Ugi Solvent DMSO Limiting Reactant 0.898 M Precipitate Yes Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp222

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP222-2 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.898 M Precipitate Yes Yield - %

191

→

t-butyl isocyanide

21106059

Comments Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



Researcher Khalid Mirza Reaction Type Ugi Solvent DMSO Limiting Reactant 0.473 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp222

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059

Reaction ID UCEXP222-4 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.473 M Precipitate Yes Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp222

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+


+


+

benzaldehyde

→

t-butyl isocyanide

Reaction ID UCEXP226-2 Researcher David Bulger Reaction Type Ugi Solvent THF Limiting Reactant 0.525 M Precipitate No Comments 0.5 mmol of isocyanide was added to 900uL of a 0.55M solution of aldehyde; amine and acid

192

24528165

Reference


+


+


+

benzaldehyde

→

n-butyl isocyanide

24528166



+


+


+

benzaldehyde

→

1-pentyl isocyanide

24528167


+


+


+

benzaldehyde

→


24528168


+


+


+

benzaldehyde

→

benzyl isocyanide


193

24528169

+


+


+

benzaldehyde

→


24528170



+


+


+

→


benzaldehyde

24528171


+


+


+

→


benzaldehyde

24528172


+

Boc-Trp-OH

+

octadecylamine

+

benzaldehyde


194

→

n-butyl isocyanide

24534192

+

Boc-Trp-OH

+

1-hexylamine

+

benzaldehyde

→

n-butyl isocyanide

24528183



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

n-butyl isocyanide

24528189


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


195

→

1-pentyl isocyanide

24528190

+

Boc-Gly-OH

+

+

furfurylamine

benzaldehyde

→


24528191



+

Boc-Gly-OH

+

+

furfurylamine

→


benzaldehyde

24528192

benzoic acid Reaction ID UCEXP174D/V2B35 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+

benzoic acid

+

furfurylamine

+


→


21106202

benzyl isocyanide Reaction ID UCEXP064C Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.393 M Precipitate Yes Yield 43.8 % Comments Solution was made up to 4 mL - methanol amount probably closer to 3 mL Reference http://usefulchem.wikispaces.com/Exp064

+

Boc-Gly-OH

+


+

veratraldehyde

Reaction ID UCEXP108C

196

→

benzyl isocyanide

10481870

Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.393 M Precipitate Yes Yield 20.4 % Comments Imine was preformed Reference http://usefulchem.wikispaces.com/Exp108

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

benzyl isocyanide

21106009



+

+


Boc-Gly-OH

+

benzaldehyde

→

benzyl isocyanide

21105565


+

formic acid

+

furfurylamine

+

2-naphthaldehyde

→

benzyl isocyanide

21106080


+

Boc-Trp-OH

+

1-heptylamine

+

o-vanillin

197

→

benzyl isocyanide

21106061


+

Boc-Trp-OH

+

+

1-octylamine

o-vanillin

→

benzyl isocyanide

21106062



+

chloroacetic acid

+

+


3-chloroaniline

→

benzyl isocyanide

24528156


+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

benzyl isocyanide

24528161


+


+


+

benzaldehyde

198

→

benzyl isocyanide

24528169


+


+

+

furfurylamine

piperonal

→

benzyl isocyanide

24528177



+

phenylacetic acid

+

furfurylamine

+


→

benzyl isocyanide

24528346


+

phenylacetic acid

+


+


→

benzyl isocyanide

24528350


+


+

methylamine

+


199

→

benzyl isocyanide

24534407


+


+

methylamine

+

m-anisaldehyde

→

benzyl isocyanide

24534408



+


+

methylamine

+

2-furaldehyde

→

benzyl isocyanide

24534403


+


+

methylamine

+

veratraldehyde

→

benzyl isocyanide

24528359


+

+

+

200

→


methylamine

veratraldehyde

benzyl isocyanide

24528359




+


+

+

methylamine

veratraldehyde

→

benzyl isocyanide

24528359

benzylamine Reaction ID UCEXP150D-V1B155 Researcher Khalid Mirza/ Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.404 M Precipitate Yes but the aldehyde alone is not soluble in methanol Yield 59 % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp150

+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601

Reaction ID UCEXP156B-V1B155 Researcher Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.678 M Precipitate Yes but reactants initially insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp156

+

crotonic acid

+

benzylamine

+


Reaction ID UCEXP159C-V1B18 Researcher Reaction Type

Emily Messner Ugi

201

→

t-butyl isocyanide

21106075

Solvent methanol Limiting Reactant 0.661 M Precipitate Yes but the aldehyde alone is not soluble in methanol Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp159

+


+

benzylamine

+


→

n-butyl isocyanide

21106077



+


+

+

benzylamine

o-vanillin

→

t-butyl isocyanide

21105846

Reaction ID UCEXP173G/V2B19 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

benzylamine

+


→

n-butyl isocyanide

21105845


+


+

benzylamine

+



Khalid Mirza

202

→

n-butyl isocyanide

21106077


+

D-(−)-Quinic acid

+

benzylamine

+


→

t-butyl isocyanide

24528104



+

mandelic acid

+

+

benzylamine

benzaldehyde

→


24528531


+

mandelic acid

+

benzylamine

+


→

n-butyl isocyanide

24528119


+


+

benzylamine

+



203

→


24528152


+

methacrylic acid

+

benzylamine

+


→

t-butyl isocyanide

21111671


Reaction ID UCEXP187-2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.06 M Precipitate Yes Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp187

+

methacrylic acid

+

benzylamine

+


→

t-butyl isocyanide

21111671


+

methacrylic acid

+

benzylamine

+


→

t-butyl isocyanide

21111671

Reaction ID UCEXP214C Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.404 M Precipitate Yes but the aldehyde alone is not soluble in methanol Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp214

+

crotonic acid

+

benzylamine

+


Reaction ID UCEXP215B

204

→

t-butyl isocyanide

21105601


+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601


Reaction ID UCEXP215F Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.661 M Precipitate Yes but not at room temperature Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp215

+


+

benzylamine

+


→

n-butyl isocyanide

21106077


+


+

benzylamine

+


→

n-butyl isocyanide

21106077


+

crotonic acid

+

benzylamine

+



Khalid Mirza

205

→

t-butyl isocyanide

21105601

Reaction Type Ugi Solvent acetonitrile Limiting Reactant 1.538 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp231

+

formic acid

+

+

benzylamine


→


24528186


Reaction ID UCEXP231-2 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1 M Precipitate aldehyde insoluble at this concentration Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp231

+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601


+


+

benzylamine

+


→

t-butyl isocyanide

24534439


+


+

benzylamine

+



David Bulger

206

→


23078615

Reaction Type Ugi Solvent methanol Limiting Reactant 1.021 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp233

+

Boc-Pro-OH

+

benzylamine

+


→

t-butyl isocyanide

24528262



+

Boc-Pro-OH

+

benzylamine

+


→


24528263


+


+

benzylamine

+


→


24534440


+


+

benzylamine

+



David Bulger Ugi

207

→

t-butyl isocyanide

24528265


+


+

benzylamine

+


→


23078615



+

Boc-Pro-OH

+

benzylamine

+


→

t-butyl isocyanide

24528262


+

Boc-Pro-OH

+

benzylamine

+


→


24528263


+


+

benzylamine

+



David Bulger Ugi

208

→

t-butyl isocyanide

24534439


+


+

benzylamine

+


→


24534440



+


+

benzylamine

+


→

t-butyl isocyanide

24528265


+


+

+


benzylamine

→

t-butyl isocyanide

24528266


+

Boc-L-Serine

+

benzylamine

+



David Bulger Ugi

209

→


24528267


+


+

+


benzylamine

→


23078614



+


+

+


benzylamine

→

t-butyl isocyanide

24528266


+


+

+


benzylamine

→


23078614


+

Fmoc-Diglycine

+

benzylamine


+


210

→

t-butyl isocyanide

24528270

Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 0.916 M Precipitate Reactants insoluble Comments Reference http://usefulchem.wikispaces.com/Exp234

+

Fmoc-Diglycine

+

benzylamine

+


→


24528271



+

Boc-diglycine

+

benzylamine

+


→

t-butyl isocyanide

24528272


+

Boc-diglycine

+

benzylamine

+


→


24528273


+

Boc-L-Serine

+

benzylamine

+



Khalid Mirza Ugi

211

→

t-butyl isocyanide

24528274


+


+

benzylamine

+


→

n-butyl isocyanide

24528277




+

formic acid

+

benzylamine

+


→

t-butyl isocyanide

24528284


+

methacrylic acid

+

benzylamine

+


→

n-butyl isocyanide

24528297


+


+

benzylamine

+



Khalid Mirza Ugi THF

212

→

t-butyl isocyanide

24528299


+

crotonic acid

+

benzylamine

+


→


24528306




+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601


+

Boc-Gly-OH

+

benzylamine

+


→


24528328


+

Boc-Gly-OH

+

benzylamine

+




213

→

t-butyl isocyanide

24528340


+


+

benzylamine

+


→

t-butyl isocyanide

24528381

Boc-diglycine



+

Boc-diglycine

+

benzylamine

+


→

t-butyl isocyanide

24528272


+

Boc-diglycine

+

benzylamine

+


→


24528273

Boc-Gly-OH Reaction ID UCEXP052E Researcher Alicia Holsey Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes Yield 32 % Comments 1M solutions of the starting materials was made Reference http://usefulchem.wikispaces.com/Exp052

+

+

+

214

→

Boc-Gly-OH


piperonal

t-butyl isocyanide

10481872



Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.393 M Precipitate Yes Yield 43.8 % Comments Solution was made up to 4 mL - methanol amount probably closer to 3 mL Reference http://usefulchem.wikispaces.com/Exp064

+

Boc-Gly-OH

+


+

veratraldehyde

→

benzyl isocyanide

10481870


+

Boc-Gly-OH

+


+

benzaldehyde

→

t-butyl isocyanide

10481766


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP104C Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.398 M

215

→

t-butyl isocyanide

21106059


Yes 12 % Imine was preformed http://usefulchem.wikispaces.com/Exp104

+

Boc-Gly-OH

+

furfurylamine

+

veratraldehyde

→

t-butyl isocyanide

21106057


Reaction ID UCEXP108C Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.393 M Precipitate Yes Yield 20.4 % Comments Imine was preformed Reference http://usefulchem.wikispaces.com/Exp108

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

benzyl isocyanide

21106009


+

+


Boc-Gly-OH

+

benzaldehyde

→

benzyl isocyanide

21105565


+

+

+

216

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

217

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP201-09 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.287 M Precipitate Yes Yield 50.28 %

218

→

t-butyl isocyanide

21106059

Comments Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059




+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP201-13 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.074 M

219

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

220

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

221

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


222

→

t-butyl isocyanide

21106059

Comments Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059




+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


223

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

224

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

225

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


226

→

t-butyl isocyanide

21106059

Comments Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059




+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP201-43 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.289 M

227

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

228

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

229

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP222-3 Researcher Khalid Mirza Reaction Type Ugi Solvent DMSO Limiting Reactant 0.473 M Precipitate No Comments -

230

→

t-butyl isocyanide

21106059

Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.473 M Precipitate Yes Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp222

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059

Reaction ID UCEXP225-1 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.631 M Precipitate Yes Yield - % Comments 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid Reference http://usefulchem.wikispaces.com/Exp225

+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528157


+

Boc-Gly-OH

+

furfurylamine

+

piperonal


231

→

n-butyl isocyanide

24528158

Product Comments Reference

Pending 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid http://usefulchem.wikispaces.com/Exp225

+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

1-pentyl isocyanide

24528159



Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.889 M Precipitate Yes Product Pending Comments 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid Reference http://usefulchem.wikispaces.com/Exp225

+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→


24528160


+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

benzyl isocyanide

24528161


+

Boc-Gly-OH

+

furfurylamine

+

piperonal


232

→


24528162


No 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid http://usefulchem.wikispaces.com/Exp225

+

Boc-Gly-OH

+

furfurylamine

+

→


piperonal

24528163



Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.868 M Precipitate No Comments 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid Reference http://usefulchem.wikispaces.com/Exp225

+

Boc-Gly-OH

+

furfurylamine

+

→


piperonal

24528164


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


Khalid Mirza Ugi

233

→

n-butyl isocyanide

24528189


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

1-pentyl isocyanide

24528190



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→


24528191


+

Boc-Gly-OH

+

furfurylamine

+

→


benzaldehyde

24528192


+

Boc-Gly-OH

+

furfurylamine

+



234

→

t-butyl isocyanide

24528193


+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528194



+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528195


+

Boc-Gly-OH

+

furfurylamine

+


→


24528196


+

Boc-Gly-OH

+

furfurylamine

+


235

→


24528197


+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528198



+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528199


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528200


+

+

+

236

→

Boc-Gly-OH

furfurylamine



21782441


+

Boc-Gly-OH

+

furfurylamine

+

→



24528201



+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde

→

t-butyl isocyanide

24528202


+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde

→

n-butyl isocyanide

24528203


+

+

+

237

→

Boc-Gly-OH

furfurylamine

crotonaldehyde

1-pentyl isocyanide

24528204


+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde

→


24528205



+

Boc-Gly-OH

+

furfurylamine

+

→


crotonaldehyde

24528206


+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528207


+

+

+

238

→

Boc-Gly-OH

furfurylamine


n-butyl isocyanide

24528208


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528209



+

Boc-Gly-OH

+

furfurylamine

+


→


24528210


+

Boc-Gly-OH

+

furfurylamine

+

→



24528211


+

+

+

239

→

Boc-Gly-OH

furfurylamine


t-butyl isocyanide

24528212



+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528213


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528214


+

Boc-Gly-OH

+

furfurylamine

+



240

→


24528215

+

Boc-Gly-OH

+

furfurylamine

+

→



24528216




+

Boc-Gly-OH

+

furfurylamine

+

2-furaldehyde

→

t-butyl isocyanide

24528217


+

Boc-Gly-OH

+

furfurylamine

+

2-furaldehyde

→

n-butyl isocyanide

24528218


+

Boc-Gly-OH

+

furfurylamine

+

2-furaldehyde

Reaction ID UCEXP232-34 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.11 M Precipitate No Comments -

241

→

1-pentyl isocyanide

24528219

Reference


+

Boc-Gly-OH

+

+

furfurylamine

2-furaldehyde

→


24528220



+

Boc-Gly-OH

+

+

furfurylamine

→


2-furaldehyde

24528221


+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528222


+

Boc-Gly-OH

+

furfurylamine

+



242

→

n-butyl isocyanide

24528223

Reference


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528224



+

Boc-Gly-OH

+

furfurylamine

+


→


24528225


+

Boc-Gly-OH

+

furfurylamine

+

→



24528226


+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde


243

→

t-butyl isocyanide

24528227

Reference


+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde

→

n-butyl isocyanide

24528228



+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde

→

1-pentyl isocyanide

24528229


+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde

→


24528230


+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde


244

→


24528231


Yes Pending http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528232




+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528233


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528234


+

Boc-Gly-OH

+

furfurylamine

+



245

→


24528235



+

Boc-Gly-OH

+

furfurylamine

+

→



24528236




+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

→

t-butyl isocyanide

24528237


+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

→

n-butyl isocyanide

24528238


+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde


246

→

1-pentyl isocyanide

24528239



+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

→


24528240




+

Boc-Gly-OH

+

furfurylamine

+

→


hexanaldehyde

24528241


+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal

→

t-butyl isocyanide

24528242


+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal


247

→

n-butyl isocyanide

24528243



+

Boc-Gly-OH

+

+

furfurylamine

trans-2-hexenal

→

1-pentyl isocyanide

24528243




+

Boc-Gly-OH

+

+

furfurylamine

trans-2-hexenal

→


24528244


+

Boc-Gly-OH

+

+

furfurylamine

→


trans-2-hexenal

24528245


+

Boc-Gly-OH

+

furfurylamine

+



248

→

t-butyl isocyanide

24534409



+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24534417




+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24534418


+

Boc-Gly-OH

+

furfurylamine

+


→


24534419


+

Boc-Gly-OH

+

furfurylamine

+



249

→


24534420



+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde

→

t-butyl isocyanide

24528251




+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde

→

n-butyl isocyanide

24528252


+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde

→

1-pentyl isocyanide

24528253


+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde


250

→


24528254



+

Boc-Gly-OH

+

furfurylamine

+

→


m-anisaldehyde

24528255




+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528256


+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528257


+

Boc-Gly-OH

+

furfurylamine

+



251

→

1-pentyl isocyanide

24528258



+

Boc-Gly-OH

+

+

furfurylamine


→


24528259




+

Boc-Gly-OH

+

+

furfurylamine

→



24528260

Reaction ID UCExp235-1 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1 M Precipitate Yes Product No Comments Reference http://usefulchem.wikispaces.com/Exp235

+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528198


+

Boc-Gly-OH

+

furfurylamine

+



Khalid Mirza Ugi

252

→


21782441

Solvent THF Limiting Reactant 1.686 M Precipitate Yes Product Awaiting Characterization Comments Reference http://usefulchem.wikispaces.com/Exp238

+

Boc-Gly-OH

+

2-chloroaniline

+


→


24528325



+

Boc-Gly-OH

+

3-chloroaniline

+


→


24528326


+

+

Boc-Gly-OH

aniline

+


→


24528327


+

Boc-Gly-OH

+

benzylamine

+



Khalid Mirza

253

→


24528328


+

Boc-Gly-OH

+

butylamine

+


→


24528329



+

Boc-Gly-OH

+

cyclohexylamine

+


→


24528330


+

Boc-Gly-OH

+

furfurylamine

+


→


24528331


+

Boc-Gly-OH

+

1-heptylamine

+



Khalid Mirza

254

→


24528332


+

Boc-Gly-OH

+

1-hexylamine

+


→


24528333



+

Boc-Gly-OH

+

methylamine

+


→


24528334


+

Boc-Gly-OH

+

1-propylamine

+


→


24528335


+

Boc-Gly-OH

+

t-butylamine

+



255

→


24528336

Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.718 M Precipitate Yes but solvent evaporated Comments Reference http://usefulchem.wikispaces.com/Exp238

+

Boc-Gly-OH

+

2-chloroaniline

+


→

t-butyl isocyanide

24528337



+

Boc-Gly-OH

+

3-chloroaniline

+


→

t-butyl isocyanide

24528338


+

+

Boc-Gly-OH

aniline

+


→

t-butyl isocyanide

24528339


+

Boc-Gly-OH

+

benzylamine

+



256

→

t-butyl isocyanide

24528340


+

Boc-Gly-OH

+

butylamine

+


→

t-butyl isocyanide

24528341



+

Boc-Gly-OH

+

cyclohexylamine

+


→

t-butyl isocyanide

24528342


+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528343


+

Boc-Gly-OH

+

1-heptylamine

+


257

→

t-butyl isocyanide

24528344

Boc-L-Serine Reaction ID UCEXP234-10 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 0.916 M Precipitate Reactants insoluble Comments Reference http://usefulchem.wikispaces.com/Exp234

+

Boc-L-Serine

+

benzylamine

+


→


24528267



+

Boc-L-Serine

+

benzylamine

+


→

t-butyl isocyanide

24528274

Boc-L-Threonine Reaction ID UCEXP234-11 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 0.893 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp234

+

+


Boc-L-Threonine

+


→

t-butyl isocyanide

24528268


+

+

+

258

→


Boc-L-Threonine



24528269

Boc-Pro-OH Reaction ID UCEXP233-11



+

Boc-Pro-OH

+

benzylamine

+


→

t-butyl isocyanide

24528262


+

Boc-Pro-OH

+

benzylamine

+


→


24528263


+

Boc-Pro-OH

+

benzylamine

+


Reaction ID UCEXP233-6 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 0.917 M Precipitate No

259

→

t-butyl isocyanide

24528262

Comments Reference


+

+

Boc-Pro-OH

benzylamine

+


→


24528263

Boc-Trp-OH Reaction ID UCEXP131-1



+

+

Boc-Trp-OH

furfurylamine

+

veratraldehyde

→

n-butyl isocyanide

21106067


+

+

Boc-Trp-OH

furfurylamine

+

veratraldehyde

→

1-pentyl isocyanide

21106068


+

Boc-Trp-OH

+


+

veratraldehyde

Reaction ID UCEXP131-4 Researcher Rikesh Parikh Reaction Type Ugi Solvent methanol Limiting Reactant 0.612 M

260

→

1-pentyl isocyanide

21106069



+

Boc-Trp-OH

+

1-heptylamine

+

o-vanillin

→

benzyl isocyanide

21106061




+

Boc-Trp-OH

+

1-octylamine

+

o-vanillin

→

benzyl isocyanide

21106062


+

Boc-Trp-OH

+

1-hexylamine

+

o-vanillin

→

n-butyl isocyanide

21106063


+

Boc-Trp-OH

+

1-hexylamine

+

o-vanillin

Reaction ID UCEXP131-8 Researcher Rikesh Parikh Reaction Type Ugi Solvent methanol Limiting Reactant 0.618 M Precipitate No Comments Protocol from Explan005 followed

261

→

1-pentyl isocyanide

21106064

Reference


+

Boc-Trp-OH

+

1-heptylamine

+

o-vanillin

→

n-butyl isocyanide

21106065



+

Boc-Trp-OH

+

1-heptylamine

+

o-vanillin

→

1-pentyl isocyanide

21106066


+

Boc-Trp-OH

+

1-propylamine

+

o-vanillin

→

n-butyl isocyanide

21106070


+

Boc-Trp-OH

+

1-propylamine

+

o-vanillin


262

→

1-pentyl isocyanide

21106071

+

Boc-Trp-OH

+

+

1-octylamine

o-vanillin

→

n-butyl isocyanide

21106072



+

Boc-Trp-OH

+

+

1-octylamine

o-vanillin

→

1-pentyl isocyanide

21106073


+

Boc-Trp-OH

+

methylamine

+


→

t-butyl isocyanide

21106045


+

Boc-Trp-OH

+

methylamine

+



263

→

n-butyl isocyanide

21106201

+

Boc-Trp-OH

+

methylamine

+


→

n-butyl isocyanide

21106193



+

Boc-Trp-OH

+

+

methylamine

benzaldehyde

→

t-butyl isocyanide

24528109


+

Boc-Trp-OH

+

octadecylamine

+


→


24528181


+

Boc-Trp-OH

+

octadecylamine

+



264

→

n-butyl isocyanide

24528182

+

Boc-Trp-OH

+

octadecylamine

+


→

n-butyl isocyanide

24534188



+

Boc-Trp-OH

+

+

octadecylamine

benzaldehyde

→

n-butyl isocyanide

24534192


+

Boc-Trp-OH

+


+


→


24534191


+

Boc-Trp-OH

+


+



265

→

n-butyl isocyanide

24534190

+

Boc-Trp-OH

+

+

octadecylamine


→

t-butyl isocyanide

24534189



+

Boc-Trp-OH

+

+

1-hexylamine

benzaldehyde

→

n-butyl isocyanide

24528183

butylamine Reaction ID UCExp236-04 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.844 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp236

+

methacrylic acid

+

butylamine

+


→

t-butyl isocyanide

24528278


+

formic acid

+

butylamine

+



266

→

t-butyl isocyanide

24528289

Reference


+

crotonic acid

+

butylamine

+


→


24528307



+

crotonic acid

+

butylamine

+


→

t-butyl isocyanide

24528318


+

Boc-Gly-OH

+

butylamine

+


→


24528329


+

Boc-Gly-OH

+

butylamine

+



267

→

t-butyl isocyanide

24528341

+


+

+


butylamine

→

t-butyl isocyanide

24528367

butyric acid Reaction ID UCEXP174Q/V2B50



+

butyric acid

+

3-chloroaniline

+


→


21106191

cbz-proline Reaction ID UCExp245-17 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.502 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp245

+

cbz-proline

+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528399


+

cbz-proline

+

furfurylamine

+

piperonal


Khalid Mirza

268

→

n-butyl isocyanide

24528399


+

cbz-proline

+


+

piperonal

→

n-butyl isocyanide

24528400



+

cbz-proline

+


+

piperonal

→

n-butyl isocyanide

24528400


+

cbz-proline

+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528401


+

cbz-proline

+

furfurylamine

+

piperonal



269

→

t-butyl isocyanide

24528401


+

cbz-proline

+

furfurylamine

+

piperonal

→


24528402




+

cbz-proline

+

furfurylamine

+

piperonal

→


24528402


+

cbz-proline

+

furfurylamine

+

→


piperonal

24528403


+

cbz-proline

+

furfurylamine

+

piperonal


Khalid Mirza Ugi

270

→


24528403


+

cbz-proline

+


+

piperonal

→

t-butyl isocyanide

24528404




+

cbz-proline

+


+

piperonal

→

t-butyl isocyanide

24528404


+

cbz-proline

+


+

→


piperonal

24528405


+

cbz-proline

+


+

piperonal


Khalid Mirza

271

→


24528405


+

cbz-proline

+

+


piperonal

→


24528406



+

cbz-proline

+

+


piperonal

→


24528406

chloroacetic acid Reaction ID UCEXP215G Researcher Khalid Mirza Reaction Type Ugi Solvent THF + methanol Limiting Reactant 0.291 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp215

+

chloroacetic acid

+

+


3-chloroaniline

→

benzyl isocyanide

24528156

crotonaldehyde Reaction ID UCEXP232-16 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.366 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp232

+

+

+

272

→

Boc-Gly-OH

furfurylamine

crotonaldehyde

t-butyl isocyanide

24528202



+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde

→

n-butyl isocyanide

24528203


+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde

→

1-pentyl isocyanide

24528204


+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde


273

→


24528205

+

Boc-Gly-OH

+

+

furfurylamine

→


crotonaldehyde

24528206

crotonic acid


Reaction ID UCEXP148A-V1B153 Researcher Khalid Mirza/ Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.398 M Precipitate Yes but the aldehyde alone is not soluble in methanol Yield 50.1 % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp148

+

crotonic acid

+

1-heptylamine

+


→

t-butyl isocyanide

21106058

Reaction ID UCEXP150D-V1B155 Researcher Khalid Mirza/ Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.404 M Precipitate Yes but the aldehyde alone is not soluble in methanol Yield 59 % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp150

+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601


+

crotonic acid

+

benzylamine

+


Reaction ID UCEXP214C Researcher Reaction Type

Khalid Mirza Ugi

274

→

t-butyl isocyanide

21106075

Solvent methanol Limiting Reactant 0.404 M Precipitate Yes but the aldehyde alone is not soluble in methanol Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp214

+

+

crotonic acid

benzylamine

+


→

t-butyl isocyanide

21105601


Reaction ID UCEXP215A Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.661 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp215

+

crotonic acid

+

1-heptylamine

+


→

t-butyl isocyanide

21106058

Reaction ID UCEXP215B Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.678 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp215

+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601


+

crotonic acid

+

benzylamine

+



Khalid Mirza

275

→

t-butyl isocyanide

21105601

Reaction Type Ugi Solvent THF Limiting Reactant 1 M Precipitate aldehyde insoluble at this concentration Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp231

+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601



+

crotonic acid

+

2-chloroaniline

+


→


24528303


+

crotonic acid

+

3-chloroaniline

+


→


24528304


+

crotonic acid

+

aniline

+




276

→


24528305


+

crotonic acid

+

benzylamine

+


→


24528306




+

crotonic acid

+

butylamine

+


→


24528307


+

crotonic acid

+

cyclohexylamine

+


→


24528308


+

crotonic acid

+

furfurylamine

+


Reaction ID UCExp238-08 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.74 M Precipitate No

277

→


24528309

Comments Reference


+

crotonic acid

+

1-heptylamine

+


→


24528310




+

crotonic acid

+

1-hexylamine

+


→


24528311


+

crotonic acid

+

methylamine

+


→


24528312


+

crotonic acid

+

1-propylamine

+



278

→


24528313

+

crotonic acid

+

t-butylamine

+


→


24528314



+

crotonic acid

+

2-chloroaniline

+


→

t-butyl isocyanide

24528315


+

crotonic acid

+

3-chloroaniline

+


→

t-butyl isocyanide

24528316


+

crotonic acid

+

aniline

+



279

→

t-butyl isocyanide

24528317

+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601



+

crotonic acid

+

butylamine

+


→

t-butyl isocyanide

24528318


+

crotonic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528319


+

crotonic acid

+

furfurylamine

+



280

→

t-butyl isocyanide

24528320

+

crotonic acid

+

1-heptylamine

+


→

t-butyl isocyanide

21106058



+

crotonic acid

+

1-hexylamine

+


→

t-butyl isocyanide

24528321


+

crotonic acid

+

methylamine

+


→

t-butyl isocyanide

24528322


+

crotonic acid

+

1-propylamine

+



281

→

t-butyl isocyanide

24528323

+

crotonic acid

+

t-butylamine

+


→

t-butyl isocyanide

24528324

cyclohexancarboxaldehyde Reaction ID UCEXP232-26



+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528212


+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528213


+

Boc-Gly-OH

+

furfurylamine

+



282

→

1-pentyl isocyanide

24528214

Reference


+

+

Boc-Gly-OH

furfurylamine

+


→


24528215



+

+

Boc-Gly-OH

furfurylamine

+

→



24528216

cyclohexylamine Reaction ID UCEXP162 Researcher Shannon Oseback Reaction Type Ugi Solvent methanol Limiting Reactant 0.285 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp162

+

phenylacetic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

21105590

Reaction ID UCEXP183-049V1 Researcher Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.398 M Precipitate Reactants Insoluble Comments Reference http://usefulchem.wikispaces.com/Exp183

+

mandelic acid

+

cyclohexylamine

+


Reaction ID UCEXP184-1/49 Researcher Reaction Type Solvent

Emily Messner Ugi ethanol

283

→

t-butyl isocyanide

24528153

Limiting Reactant 0.398 M Precipitate Reactants insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp184

+

mandelic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528154

Reaction ID UCEXP184-2/49


Researcher Emily Messner Reaction Type Ugi Solvent acetonitrile Limiting Reactant 0.398 M Precipitate Reactants insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp184

+

mandelic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528154

Reaction ID UCEXP184-3/49 Researcher Emily Messner Reaction Type Ugi Solvent dichloromethane Limiting Reactant 0.398 M Precipitate Reactants insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp184

+

mandelic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528154


+


+

cyclohexylamine

+



284

→

t-butyl isocyanide

24528302

Comments Reference


+

crotonic acid

+

cyclohexylamine

+


→


24528308




+

crotonic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528319


+

Boc-Gly-OH

+

cyclohexylamine

+


→


24528330


+

Boc-Gly-OH

+

cyclohexylamine

+



285

→

t-butyl isocyanide

24528342

+

+


cyclohexylamine

+


→

t-butyl isocyanide

24528373




+

+

Boc-Gly-OH

furfurylamine

+

piperonal

→


24528160


+


+


+

benzaldehyde

→


24528168


+


+

furfurylamine

+

piperonal



286

→


24528176

Limiting Reactant 1.098 M Precipitate Yes Product Pending Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

+

furfurylamine

benzaldehyde

→


24528191



+

Boc-Gly-OH

+

+

furfurylamine


→


24528196


+

Boc-Gly-OH

+

furfurylamine

+


→


21782441


+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde


Khalid Mirza Ugi

287

→


24528205


+

Boc-Gly-OH

+

+

furfurylamine


→


24528210



+

Boc-Gly-OH

+

furfurylamine

+


→


24528215


+

Boc-Gly-OH

+

+

furfurylamine

2-furaldehyde

→


24528220


+

Boc-Gly-OH

+

furfurylamine

+




288

→


24528225

Limiting Reactant 1.083 M Precipitate Yes Product Pending Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

+

furfurylamine

o-tolualdehyde

→


24528230



+

Boc-Gly-OH

+

furfurylamine

+


→


24528235


+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

→


24528240


+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal



289

→


24528244


+

Boc-Gly-OH

+

furfurylamine

+


→


24534419




+

Boc-Gly-OH

+

+

furfurylamine

m-anisaldehyde

→


24528254


+

Boc-Gly-OH

+

+

furfurylamine


→


24528259


+


+

benzylamine

+


Reaction ID UCEXP233-12 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 1.018 M

290

→


23078615



+

Boc-Pro-OH

+

benzylamine

+


→


24528263




+


+

benzylamine

+


→


24534440


+


+

benzylamine

+


→


23078615


+

Boc-Pro-OH

+

benzylamine

+


Reaction ID UCEXP233-8 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 1.018 M

291

→


24528263



+

+


benzylamine

+


→


24534440



Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 0.916 M Precipitate Reactants insoluble Comments Reference http://usefulchem.wikispaces.com/Exp234

+

+

Boc-L-Serine

benzylamine

+


→


24528267


+

+


Boc-L-Threonine

+


→


24528269


+


+

benzylamine

+



David Bulger Ugi

292

→


23078614


+

+


+


benzylamine

→


23078614



+

+

Fmoc-Diglycine

benzylamine

+


→


24528271


+

+

Boc-diglycine

benzylamine

+


→


24528273


+

Boc-Gly-OH

+

furfurylamine

+



Khalid Mirza

293

→


21782441

Reaction Type Ugi Solvent THF Limiting Reactant 1.881 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp238

+

crotonic acid

+

2-chloroaniline

+


→


24528303



+

crotonic acid

+

3-chloroaniline

+


→


24528304


+

+

crotonic acid

aniline

+


→


24528305


+

crotonic acid

+

benzylamine

+




294

→


24528306


+

crotonic acid

+

butylamine

+


→


24528307




+

crotonic acid

+

cyclohexylamine

+


→


24528308


+

crotonic acid

+

furfurylamine

+


→


24528309


+

crotonic acid

+

1-heptylamine

+



295

→


24528310

Comments Reference


+

crotonic acid

+

1-hexylamine

+


→


24528311




+

crotonic acid

+

methylamine

+


→


24528312


+

crotonic acid

+

1-propylamine

+


→


24528313


+

crotonic acid

+

t-butylamine

+


Reaction ID UCExp238-25 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.686 M Precipitate Yes Product Awaiting Characterization Comments -

296

→


24528314

Reference


+

Boc-Gly-OH

+

2-chloroaniline

+


→


24528325



+

Boc-Gly-OH

+

3-chloroaniline

+


→


24528326


+

+

Boc-Gly-OH

aniline

+


→


24528327


+

Boc-Gly-OH

+

benzylamine

+


Reaction ID UCExp238-29 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.704 M Precipitate Yes Product Awaiting Characterization

297

→


24528328

Comments Reference


+

Boc-Gly-OH

+

butylamine

+


→


24528329




+

Boc-Gly-OH

+

cyclohexylamine

+


→


24528330


+

Boc-Gly-OH

+

furfurylamine

+


→


24528331


+

Boc-Gly-OH

+

1-heptylamine

+



298

→


24528332

Comments Reference


+

Boc-Gly-OH

+

1-hexylamine

+


→


24528333




+

Boc-Gly-OH

+

methylamine

+


→


24528334


+

Boc-Gly-OH

+

1-propylamine

+


→


24528335


+

Boc-Gly-OH

+

t-butylamine

+



299

→


24528336

Comments Reference


+

phenylacetic acid

+

furfurylamine

+


→


24528345




+

phenylacetic acid

+


+


→


21782450


+


+

methylamine

+

veratraldehyde

→


21782465


+


+

methylamine

+

veratraldehyde


Marshall Moritz

300

→


21782465

Reaction Type Ugi Solvent benzene Limiting Reactant 0.432 M Precipitate Yes Product No Comments Reference http://usefulchem.wikispaces.com/Exp242

+

phenylacetic acid

+

furfurylamine

+


→


24528384



+

phenylacetic acid

+


+


→


24528389


+


+

furfurylamine

+

piperonal

→


24528394


+


+

furfurylamine

+

piperonal

301

→


24528394


+


+


+

piperonal

→


24528397



+


+


+

piperonal

→


24528397


+

cbz-proline

+

furfurylamine

+

piperonal

→


24528402


+

cbz-proline

+

furfurylamine

+

piperonal

302

→


24528402


+

cbz-proline

+

+


piperonal

→


24528406



+

cbz-proline

+

+


piperonal

→


24528406

D-(−)-Quinic acid Reaction ID UCEXP174O/V2B47 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+

D-(−)-Quinic acid

+


+


→

t-butyl isocyanide

21106186


+

+

+

303

→

D-(−)-Quinic acid

benzylamine


t-butyl isocyanide

24528104


+

D-(−)-Quinic acid

+

+

methylamine


→


24528131



+

D-(−)-Quinic acid

+

methylamine

+


→


24528134


+

D-(−)-Quinic acid

+

methylamine

+

2-naphthaldehyde

→


24528138

decanoic acid Reaction ID UCEXP173N/V2B26 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.217 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+

+

+

304

→

decanoic acid

2-chloroaniline

o-vanillin


21105847



+

decanoic acid

+

2-chloroaniline

+


→


24528124

diphenylacetaldehyde Reaction ID UCEXP232-21 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.008 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528207


+

Boc-Gly-OH

+

furfurylamine

+



305

→

n-butyl isocyanide

24528208

Reference


+

Boc-Gly-OH

+

+

furfurylamine


→

1-pentyl isocyanide

24528209




+

Boc-Gly-OH

+

+

furfurylamine


→


24528210


+

Boc-Gly-OH

+

+

furfurylamine

→



24528211

diphenylacetic acid Reaction ID UCEXP181-076V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.224 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+

diphenylacetic acid

+

1-propylamine

+


Reaction ID UCEXP181-088V2 Researcher Reaction Type

Khalid Mirza Ugi

306

→

n-butyl isocyanide

24528112


+

diphenylacetic acid

+


+


→

n-butyl isocyanide

24528532




+

diphenylacetic acid

+

methylamine

+


→

n-butyl isocyanide

24528148

Fmoc-Diglycine Reaction ID UCEXP234-5 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 0.918 M Precipitate Reactants insoluble Comments Reference http://usefulchem.wikispaces.com/Exp234

+

Fmoc-Diglycine

+

benzylamine

+


→

t-butyl isocyanide

24528270


+

Fmoc-Diglycine

+

benzylamine

+


307

→


24528271

formic acid Reaction ID UCEXP130-1 Researcher Rikesh Parikh Reaction Type Ugi Solvent methanol Limiting Reactant 0.751 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp130

+

formic acid

+


+

2-naphthaldehyde

→

n-butyl isocyanide

21106081



+

formic acid

+

1-hexylamine

+

2-naphthaldehyde

→

1-pentyl isocyanide

21106078


+

formic acid

+


+

benzaldehyde

→


21106060


+

formic acid

+

furfurylamine

+

2-naphthaldehyde

308

→

benzyl isocyanide

21106080


+

formic acid

+

+

furfurylamine

2-naphthaldehyde

→

n-butyl isocyanide

21106079



+

formic acid

+

+

benzylamine


→


24528186


+

formic acid

+

t-butylamine

+


→

t-butyl isocyanide

24528279


+

formic acid

+

3-chloroaniline

+



309

→

t-butyl isocyanide

24528281


+

formic acid

+

benzylamine

+


→

t-butyl isocyanide

24528284



+

formic acid

+

butylamine

+


→

t-butyl isocyanide

24528289


+

formic acid

+

methylamine

+


→

n-butyl isocyanide

24528292


+

formic acid

+

aniline

+


furfurylamine 310

→

t-butyl isocyanide

24528294


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


Reaction ID UCEXP104C Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.398 M Precipitate Yes Yield 12 % Comments Imine was preformed Reference http://usefulchem.wikispaces.com/Exp104

+

Boc-Gly-OH

+

furfurylamine

+

veratraldehyde

→

t-butyl isocyanide

21106057

Reaction ID UCEXP108C Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.393 M Precipitate Yes Yield 20.4 % Comments Imine was preformed Reference http://usefulchem.wikispaces.com/Exp108

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

benzyl isocyanide

21106009


+

+

+

311

→

formic acid

furfurylamine

2-naphthaldehyde

benzyl isocyanide

21106080


+

formic acid

+

+

furfurylamine

2-naphthaldehyde

→

n-butyl isocyanide

21106079



+

Boc-Trp-OH

+

+

furfurylamine

veratraldehyde

→

n-butyl isocyanide

21106067


+

Boc-Trp-OH

+

+

furfurylamine

veratraldehyde

→

1-pentyl isocyanide

21106068

Reaction ID UCEXP160C-V1B19 Researcher Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.388 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp160

+


+

furfurylamine

+


312

→

n-butyl isocyanide

21105579

Reaction ID UCEXP163A-V1B14 Researcher Tim Bohinsky Reaction Type Ugi Solvent methanol Limiting Reactant 0.387 M Precipitate no and aldehyde alone not solube Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp163

+

mandelic acid

+

furfurylamine

+


→

t-butyl isocyanide

21105596



+


+

+

furfurylamine

2-naphthaldehyde

→


21106054


+


+

furfurylamine

+


→

t-butyl isocyanide

21106041


+


+

furfurylamine

+


313

→


21106051


+


+

furfurylamine

+


→


21106043



+


+

furfurylamine

+

benzaldehyde

→


21105843


+


+

furfurylamine

+


→


21106042


+

+

+

314

→


furfurylamine



21106204


+

benzoic acid

+

furfurylamine

+


→


21106202



+


+

furfurylamine

+


→


21106187

Reaction ID UCEXP176C Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant - M Precipitate Yes Yield 62 % Comments aldehyde not soluble until all reactants added Reference http://usefulchem.wikispaces.com/Exp176

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594

Reaction ID UCEXP178 Researcher Shannon Oseback Reaction Type Ugi Solvent methanol Limiting Reactant 0.388 M Precipitate Yes but the aldehyde alone is not soluble in methanol Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp178

+

+

+

315

→

phenylacetic acid

furfurylamine


n-butyl isocyanide

21105594



+


+

furfurylamine

+


→

n-butyl isocyanide

24528097


+


+

furfurylamine

+


→


24528100


+


+

furfurylamine

+



316

→


24528106

+

mandelic acid

+

furfurylamine

+


→

n-butyl isocyanide

24528111



+


+

furfurylamine

+


→

t-butyl isocyanide

24528115


+


+

furfurylamine

+


→


24528118


+


+

furfurylamine

+



317

→


24528126

+


+

furfurylamine

+


→


24528128



+


+

+

furfurylamine

veratraldehyde

→


24534442


+


+

furfurylamine

+


→


24528151


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


318

→

t-butyl isocyanide

21106059

Yield Comments Reference

59.07 % Automated liquid handling http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059




+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde



319

→

t-butyl isocyanide

21106059

Limiting Reactant 0.998 M Precipitate Yes Yield 69.22 % Comments Automated liquid handling Reference http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

320

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

321

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


322

→

t-butyl isocyanide

21106059

Comments Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059




+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


323

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

324

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

325

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


326

→

t-butyl isocyanide

21106059

Comments Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059




+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


327

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

328

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

329

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP201-47 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.287 M Precipitate Yes Yield 7.44 %

330

→

t-butyl isocyanide

21106059

Comments Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.286 M Precipitate Yes Yield 12.06 % Comments Automated liquid handling Reference http://usefulchem.wikispaces.com/Exp201

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP217-5 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.384 M

331

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

21105594



Researcher Khalid Mirza Reaction Type Ugi Solvent DMSO Limiting Reactant 0.898 M Precipitate Yes Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp222

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059

Reaction ID UCEXP222-3 Researcher Khalid Mirza Reaction Type Ugi Solvent DMSO Limiting Reactant 0.473 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp222

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde



332

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528157


+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528158


+

Boc-Gly-OH

+

furfurylamine

+

piperonal

333

→

1-pentyl isocyanide

24528159


+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→


24528160



+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

benzyl isocyanide

24528161


+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→


24528162


+

Boc-Gly-OH

+

furfurylamine

+

piperonal

334

→


24528163


+

Boc-Gly-OH

+

furfurylamine

+

→


piperonal

24528164



+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528173


+


+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528174


+


+

furfurylamine

+

piperonal

335

→

1-pentyl isocyanide

24528175


+


+

furfurylamine

+

piperonal

→


24528176



+


+

furfurylamine

+

piperonal

→

benzyl isocyanide

24528177


+


+

furfurylamine

+

piperonal

→


24528178


+


+

furfurylamine

+

piperonal

336

→


24528179


+


+

furfurylamine

+

→


piperonal

24528180



+


+

furfurylamine

+

2-furaldehyde

→

n-butyl isocyanide

24528187


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

337

→

Boc-Gly-OH

furfurylamine

benzaldehyde

n-butyl isocyanide

24528189


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

1-pentyl isocyanide

24528190



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→


24528191


+

Boc-Gly-OH

+

furfurylamine

+

→


benzaldehyde

24528192


+

+

+

338

→

Boc-Gly-OH

furfurylamine


t-butyl isocyanide

24528193



+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528194


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528195


+

Boc-Gly-OH

+

furfurylamine

+



339

→


24528196

+

Boc-Gly-OH

+

+

furfurylamine

→



24528197




+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528198


+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528199


+

Boc-Gly-OH

+

furfurylamine

+



340

→

1-pentyl isocyanide

24528200



+

Boc-Gly-OH

+

furfurylamine

+


→


21782441




+

Boc-Gly-OH

+

furfurylamine

+

→



24528201


+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde

→

t-butyl isocyanide

24528202


+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde



341

→

n-butyl isocyanide

24528203


+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde

→

1-pentyl isocyanide

24528204




+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde

→


24528205


+

Boc-Gly-OH

+

furfurylamine

+

→


crotonaldehyde

24528206


+

Boc-Gly-OH

+

furfurylamine

+




342

→

t-butyl isocyanide

24528207


+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528208




+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528209


+

Boc-Gly-OH

+

furfurylamine

+


→


24528210


+

Boc-Gly-OH

+

furfurylamine

+



Khalid Mirza Ugi

343

→


24528211


+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528212




+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528213


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528214


+

Boc-Gly-OH

+

furfurylamine

+



344

→


24528215



+

Boc-Gly-OH

+

furfurylamine

+

→



24528216



+

Boc-Gly-OH

+

furfurylamine

+

2-furaldehyde

→

t-butyl isocyanide

24528217


+

Boc-Gly-OH

+

furfurylamine

+

2-furaldehyde

→

n-butyl isocyanide

24528218


+

Boc-Gly-OH

+

furfurylamine

+

2-furaldehyde



345

→

1-pentyl isocyanide

24528219


+

Boc-Gly-OH

+

+

furfurylamine

2-furaldehyde

→


24528220




+

Boc-Gly-OH

+

+

furfurylamine

→


2-furaldehyde

24528221


+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528222


+

Boc-Gly-OH

+

furfurylamine

+




346

→

n-butyl isocyanide

24528223


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528224




+

Boc-Gly-OH

+

furfurylamine

+


→


24528225


+

Boc-Gly-OH

+

furfurylamine

+

→



24528226


+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde



347

→

t-butyl isocyanide

24528227


+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde

→

n-butyl isocyanide

24528228




+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde

→

1-pentyl isocyanide

24528229


+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde

→


24528230


+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde


Khalid Mirza

348

→


24528231

Reaction Type Ugi Solvent methanol Limiting Reactant 1.066 M Precipitate Yes Product Pending Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528232



+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528233


+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24528234


+

Boc-Gly-OH

+

furfurylamine

+



Khalid Mirza

349

→


24528235


+

Boc-Gly-OH

+

furfurylamine

+

→



24528236



+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

→

t-butyl isocyanide

24528237


+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

→

n-butyl isocyanide

24528238


+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde


Khalid Mirza

350

→

1-pentyl isocyanide

24528239


+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

→


24528240



+

Boc-Gly-OH

+

furfurylamine

+

→


hexanaldehyde

24528241


+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal

→

t-butyl isocyanide

24528242


+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal


Khalid Mirza

351

→

n-butyl isocyanide

24528243


+

Boc-Gly-OH

+

+

furfurylamine

trans-2-hexenal

→

1-pentyl isocyanide

24528243



+

Boc-Gly-OH

+

+

furfurylamine

trans-2-hexenal

→


24528244


+

Boc-Gly-OH

+

+

furfurylamine

→


trans-2-hexenal

24528245


+

Boc-Gly-OH

+

furfurylamine

+



Khalid Mirza

352

→

t-butyl isocyanide

24534409


+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24534417



+

Boc-Gly-OH

+

furfurylamine

+


→

1-pentyl isocyanide

24534418


+

Boc-Gly-OH

+

furfurylamine

+


→


24534419


+

Boc-Gly-OH

+

furfurylamine

+



Khalid Mirza

353

→


24534420


+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde

→

t-butyl isocyanide

24528251



+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde

→

n-butyl isocyanide

24528252


+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde

→

1-pentyl isocyanide

24528253


+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde


Khalid Mirza

354

→


24528254


+

Boc-Gly-OH

+

furfurylamine

+

→


m-anisaldehyde

24528255



+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528256


+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528257


+

Boc-Gly-OH

+

furfurylamine

+



Khalid Mirza

355

→

1-pentyl isocyanide

24528258


+

Boc-Gly-OH

+

+

furfurylamine


→


24528259



+

Boc-Gly-OH

+

+

furfurylamine

→



24528260


+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528198


+

Boc-Gly-OH

+

furfurylamine

+


356

→


21782441

Reaction ID UCExp237-01 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.778 M Precipitate Yes Product Awaiting Characterization Comments Reference http://usefulchem.wikispaces.com/Exp237

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

crotonic acid

+

furfurylamine

+


→


24528309


+

crotonic acid

+

furfurylamine


+


357

→

t-butyl isocyanide

24528320


+

Boc-Gly-OH

+

furfurylamine

+


→


24528331



+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528343

Reaction ID UCExp240-01 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.607 M Precipitate Yes but after 48h Comments Reference http://usefulchem.wikispaces.com/Exp240

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+



358

→

t-butyl isocyanide

21791788


+

phenylacetic acid

+

furfurylamine

+


→


24528345



+

phenylacetic acid

+

furfurylamine

+

→



21782583


+

phenylacetic acid

+

furfurylamine

+


→

benzyl isocyanide

24528346


+

phenylacetic acid

+

furfurylamine

+


359

→

1-pentyl isocyanide

24528347


+


+

furfurylamine

+


→

t-butyl isocyanide

24528376



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

t-butyl isocyanide

24528383


+

phenylacetic acid

+

furfurylamine

+


360

→


24528384


+

phenylacetic acid

+

furfurylamine

+

→



24528385



+

phenylacetic acid

+

furfurylamine

+


→

1-pentyl isocyanide

24528386


+


+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528391


+

+

+

361

→


furfurylamine

piperonal

n-butyl isocyanide

24528391




+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528393


+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528393


+


+

furfurylamine

+

piperonal


Khalid Mirza Ugi

362

→


24528394


+


+

furfurylamine

+

piperonal

→


24528394



+


+

furfurylamine

+

→


piperonal

24528395


+


+

furfurylamine

+

→


piperonal

24528395


+

cbz-proline

+

furfurylamine

+

piperonal

363

→

n-butyl isocyanide

24528399


+

cbz-proline

+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528399



+

cbz-proline

+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528401


+

cbz-proline

+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528401


+

cbz-proline

+

furfurylamine

+

piperonal


364

→


24528402


+

cbz-proline

+

furfurylamine

+

piperonal

→


24528402



+

cbz-proline

+

furfurylamine

+

→


piperonal

24528403


+

cbz-proline

+

furfurylamine

+

→


piperonal

24528403


+


+

furfurylamine

+

piperonal

365

→

t-butyl isocyanide

24528407


+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528407



+


+

furfurylamine

+

→


piperonal

24528408


+


+

furfurylamine

+

→


piperonal

24528408


+

+

+

366

→


furfurylamine

piperonal

n-butyl isocyanide

24528409




+


+

+

furfurylamine

piperonal

→

n-butyl isocyanide

24528409

Reaction ID UCExp252-01 Researcher Khalid Mirza Reaction Type Ugi Solvent benzene Limiting Reactant 0.403 M Precipitate Yes Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp252

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594

Reaction ID UCExp253-01 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.53 M Precipitate Yes Yield 42.6 % Comments Reference http://usefulchem.wikispaces.com/Exp253

+

phenylacetic acid

+

furfurylamine

+



367

→

n-butyl isocyanide

21105594


Yes - % http://usefulchem.wikispaces.com/Exp254

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


368

→

n-butyl isocyanide

21105594

Reaction ID UCExp255-04 Researcher Khalid Mirza Reaction Type Ugi Solvent benzene Limiting Reactant 0.4 M Precipitate Yes Yield 29.7 % Comments Reference http://usefulchem.wikispaces.com/Exp255

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594

Reaction ID UCExp256-01 Researcher Khalid Mirza Reaction Type Ugi Solvent benzene Limiting Reactant 0.4 M Precipitate Yes Yield 17 % Comments Reference http://usefulchem.wikispaces.com/Exp256

+

+

+

369

→

phenylacetic acid

furfurylamine


n-butyl isocyanide

21105594

Reaction ID UCExp257-01 Researcher Khalid Mirza Reaction Type Ugi Solvent ethyl acetate Limiting Reactant 0.37 M Precipitate Yes Yield 24 % Comments Reference http://usefulchem.wikispaces.com/Exp257


+

+

phenylacetic acid

furfurylamine

+


→

n-butyl isocyanide

21105594

furoic acid Reaction ID UCEXP182 Researcher Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.398 M Precipitate Reactants Insoluble Comments Reference http://usefulchem.wikispaces.com/Exp182

+

+

furoic acid

1-heptylamine

+


→

n-butyl isocyanide

21168529

glycine methyl ester hydrochloride Reaction ID UCEXP234-11 Researcher David Bulger Reaction Type Ugi Solvent methanol Limiting Reactant 0.893 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp234

+

Boc-L-Threonine

+


+



David Bulger

370

→

t-butyl isocyanide

24528268


+

+


Boc-L-Threonine

+


→


24528269

glycolic acid



+

glycolic acid

+

1-heptylamine

+


→


24528188

hexanaldehyde Reaction ID UCEXP232-51 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.106 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

→

t-butyl isocyanide

24528237


+

+

+

371

→

Boc-Gly-OH

furfurylamine

hexanaldehyde

n-butyl isocyanide

24528238



+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

→

1-pentyl isocyanide

24528239


+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

→


24528240


+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

hexanoic acid Reaction ID UCEXP181-089V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M

372

→


24528241


Reactants Insoluble Protocol from Explan005 followed http://usefulchem.wikispaces.com/Exp181

+

hexanoic acid

+

3-chloroaniline

+


→


24528122




+

+

hexanoic acid

aniline

+


→


24528125

m-anisaldehyde Reaction ID UCEXP232-66 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.067 M Precipitate Yes Product Pending Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde

→

t-butyl isocyanide

24528251


+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde


Khalid Mirza Ugi

373

→

n-butyl isocyanide

24528252


+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde

→

1-pentyl isocyanide

24528253



+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde

→


24528254


+

Boc-Gly-OH

+

furfurylamine

+

→


m-anisaldehyde

24528255


+


+

methylamine

+

m-anisaldehyde

374

→

benzyl isocyanide

24534408

mandelic acid Reaction ID UCEXP163A-V1B14 Researcher Tim Bohinsky Reaction Type Ugi Solvent methanol Limiting Reactant 0.387 M Precipitate no and aldehyde alone not solube Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp163

+

mandelic acid

+

furfurylamine

+


→

t-butyl isocyanide

21105596



+

mandelic acid

+

3-chloroaniline

+


→


21106190


+

mandelic acid

+

benzylamine

+

benzaldehyde

→


24528531


+

+

+

375

→

mandelic acid

furfurylamine


n-butyl isocyanide

24528111


+

mandelic acid

+

benzylamine

+


→

n-butyl isocyanide

24528119



+

mandelic acid

+

methylamine

+


→

n-butyl isocyanide

24528133


+

mandelic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528153

Reaction ID UCEXP184-1/49 Researcher Emily Messner Reaction Type Ugi Solvent ethanol Limiting Reactant 0.398 M Precipitate Reactants insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp184

+

mandelic acid

+

cyclohexylamine

+


376

→

t-butyl isocyanide

24528154

Reaction ID UCEXP184-2/49 Researcher Emily Messner Reaction Type Ugi Solvent acetonitrile Limiting Reactant 0.398 M Precipitate Reactants insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp184

+

mandelic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528154



+

mandelic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528154

methacrylic acid Reaction ID UCEXP174I/V2B41 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.224 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174

+

+

methacrylic acid

aniline

+


→


21106198


+

methacrylic acid

+


+


377

→

t-butyl isocyanide

21111670


+

methacrylic acid

+

benzylamine

+


→

t-butyl isocyanide

21111671



+

methacrylic acid

+


+


→

t-butyl isocyanide

21111670


+

methacrylic acid

+

benzylamine

+


→

t-butyl isocyanide

21111671


+

methacrylic acid

+

t-butylamine

+


378

→

t-butyl isocyanide

21143155


+

methacrylic acid

+


+


→

t-butyl isocyanide

21111670



+

methacrylic acid

+

benzylamine

+


→

t-butyl isocyanide

21111671


+

methacrylic acid

+

t-butylamine

+


→

t-butyl isocyanide

21143155


+

methacrylic acid

+

butylamine

+



379

→

t-butyl isocyanide

24528278


+

methacrylic acid

+

methylamine

+


→

n-butyl isocyanide

24528283



+

+

methacrylic acid

aniline

+


→

t-butyl isocyanide

24528285


+

methacrylic acid

+

t-butylamine

+


→

n-butyl isocyanide

24528293


+

methacrylic acid

+

3-chloroaniline

+



Khalid Mirza Ugi

380

→

n-butyl isocyanide

24528296


+

+

methacrylic acid

benzylamine

+


→

n-butyl isocyanide

24528297




+

+

methacrylic acid

1-hexylamine

+


→

t-butyl isocyanide

24528301

methoxy acetic ac id Reaction ID UCEXP231-4 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 2 M Precipitate Yes Product Pending Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp231

+


+


+


→

n-butyl isocyanide

21486238

methylamine Reaction ID UCEXP147-1V2B1 Researcher Mitesh Shah Reaction Type Ugi Solvent methanol Limiting Reactant 0.659 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp147

+

+

+

381

→


methylamine



21105839


+


+

+

methylamine

2-naphthaldehyde

→

t-butyl isocyanide

21105841


Reaction ID UCEXP151-1V2B10 Researcher Mitesh Shah Reaction Type Ugi Solvent methanol Limiting Reactant 0.694 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp151

+


+

methylamine

+


→


21106049

Reaction ID UCEXP171A/V2B1 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate Yes Product Impurities found Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

methylamine

+


→


21105839


+

+

+

382

→


methylamine



21106040


+


+

+

methylamine

2-naphthaldehyde

→

t-butyl isocyanide

21105841


Reaction ID UCEXP171HV2B8 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes Product No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

methylamine

+


→


21105832


+


+

methylamine

+


Reaction ID UCEXP171KV2B11 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate Yes Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

383

→


21106049

+


+

methylamine

+


→

t-butyl isocyanide

21105842



+


+

methylamine

+


→

t-butyl isocyanide

21106039


+


+

+

methylamine


→

t-butyl isocyanide

21105844


+


+

methylamine

+



384

→

t-butyl isocyanide

21106044

+


+

methylamine

+


→

n-butyl isocyanide

21106048



+

Boc-Trp-OH

+

methylamine

+


→

t-butyl isocyanide

21106045


+


+

methylamine

+


→


21106052


+


+

methylamine

+



385

→

t-butyl isocyanide

21106038

+


+

methylamine

+


→

t-butyl isocyanide

21106050

Reaction ID UCEXP174C/V2B34 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.226 M Precipitate Yes but the aldehyde alone is not soluble in methanol Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp174


+


+

methylamine

+


→

n-butyl isocyanide

21106205


+

Boc-Trp-OH

+

methylamine

+


→

n-butyl isocyanide

21106201


+


+

methylamine

+

veratraldehyde


386

→


21106200

+


+

+

methylamine

2-naphthaldehyde

→


21106188



+


+

methylamine

+


→


21106195


+

Boc-Trp-OH

+

methylamine

+


→

n-butyl isocyanide

21106193


+


+

methylamine

+



387

→

n-butyl isocyanide

21106203

+


+

methylamine

+


→


24528098



+


+

+

methylamine


→


24528099


+


+

methylamine

+


→


24528101


+


+

methylamine

+



388

→


24528105

+


+

+

methylamine

o-vanillin

→


24528107



+


+

methylamine

+


→


21106207


+

Boc-Trp-OH

+

+

methylamine

benzaldehyde

→

t-butyl isocyanide

24528109


+


+

methylamine

+



389

→


24528121

+


+

methylamine

+


→

t-butyl isocyanide

21106206



+

4-nitrobenzoic acid

+

methylamine

+


→


24528123


+


+

methylamine

+


→


24528127


+


+

methylamine

+



390

→


24528129

+

D-(−)-Quinic acid

+

+

methylamine


→


24528131



+


+

methylamine

+


→


24528132


+

mandelic acid

+

methylamine

+


→

n-butyl isocyanide

24528133


+

D-(−)-Quinic acid

+

methylamine

+



391

→


24528134

+


+

+

methylamine

2-naphthaldehyde

→


24528136



+

D-(−)-Quinic acid

+

+

methylamine

2-naphthaldehyde

→


24528138


+


+

methylamine

+


→

t-butyl isocyanide

24528534


+


+

methylamine

+



392

→


24528141

+


+

+

methylamine


→


24528145



+


+

+


methylamine

→


24528147


+

diphenylacetic acid

+

methylamine

+


→

n-butyl isocyanide

24528148


+


+

methylamine

+



393

→


24528149

+


+

+

methylamine

2-naphthaldehyde

→

t-butyl isocyanide

21105841

Reaction ID UCEXP215D Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.66 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp215


+


+

methylamine

+


→

t-butyl isocyanide

21105842


+


+

+

methylamine


→

t-butyl isocyanide

24528155


+


+

methylamine

+



394

→

t-butyl isocyanide

21105842

+


+

+

methylamine


→

t-butyl isocyanide

21105844



+


+

+

methylamine


→

t-butyl isocyanide

21105844


+


+

+

methylamine

2-naphthaldehyde

→

t-butyl isocyanide

21105841


+

methacrylic acid

+

methylamine

+



395

→

n-butyl isocyanide

24528283

+


+

+


methylamine

→

t-butyl isocyanide

24528287



+


+

methylamine

+


→

t-butyl isocyanide

24528291


+

formic acid

+

methylamine

+


→

n-butyl isocyanide

24528292


+

crotonic acid

+

methylamine

+



396

→


24528312

+

crotonic acid

+

methylamine

+


→

t-butyl isocyanide

24528322



+

Boc-Gly-OH

+

methylamine

+


→


24528334


+


+

methylamine

+


→

benzyl isocyanide

24534407


+


+

methylamine

+

m-anisaldehyde


397

→

benzyl isocyanide

24534408

Comments Reference


+


+

methylamine

+

2-furaldehyde

→

benzyl isocyanide

24534403




+


+

methylamine

+

veratraldehyde

→

n-butyl isocyanide

24528355


+


+

methylamine

+

veratraldehyde

→

n-butyl isocyanide

24528355


+


+

methylamine

+

veratraldehyde


398

→

t-butyl isocyanide

24528356


+


+

methylamine

+

veratraldehyde

→

t-butyl isocyanide

24528356



+


+

methylamine

+

veratraldehyde

→


21782465


+


+

methylamine

+

veratraldehyde

→


21782465


+

+

+

399

→


methylamine


veratraldehyde

24528357




+


+

methylamine

+

→


veratraldehyde

24528357


+


+

methylamine

+

veratraldehyde

→

1-pentyl isocyanide

24528358


+


+

methylamine

+

veratraldehyde


Khalid Mirza Ugi

400

→

1-pentyl isocyanide

24528358


+


+

+

methylamine

veratraldehyde

→

benzyl isocyanide

24528359



+


+

+

methylamine

veratraldehyde

→

benzyl isocyanide

24528359


+


+

+

methylamine

veratraldehyde

→

benzyl isocyanide

24528359


+


+

methylamine

+


401

→

t-butyl isocyanide

24528360


+


+

methylamine

+


→

t-butyl isocyanide

24528361



+


+

methylamine

+


→

t-butyl isocyanide

24528362


+


+

methylamine

+

o-tolualdehyde

→

t-butyl isocyanide

24528363


+

+

+

402

→



methylamine

n-butyl isocyanide

24528364




+

+


methylamine

+


→

n-butyl isocyanide

24528365

n-butyl isocyanide Reaction ID UCEXP130-1 Researcher Rikesh Parikh Reaction Type Ugi Solvent methanol Limiting Reactant 0.751 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp130

+

formic acid

+


+

2-naphthaldehyde

→

n-butyl isocyanide

21106081


+

formic acid

+

furfurylamine

+

2-naphthaldehyde



403

→

n-butyl isocyanide

21106079


+

Boc-Trp-OH

+

furfurylamine

+

veratraldehyde

→

n-butyl isocyanide

21106067




+

Boc-Trp-OH

+

1-hexylamine

+

o-vanillin

→

n-butyl isocyanide

21106063


+

Boc-Trp-OH

+

1-heptylamine

+

o-vanillin

→

n-butyl isocyanide

21106065


+

Boc-Trp-OH

+

1-propylamine

+

o-vanillin

Reaction ID UCEXP134-3 Researcher Rikesh Parikh Reaction Type Ugi Solvent methanol Limiting Reactant 0.612 M Precipitate No

404

→

n-butyl isocyanide

21106070

Comments Reference


+

Boc-Trp-OH

+

+

1-octylamine

o-vanillin

→

n-butyl isocyanide

21106072

Reaction ID UCEXP159C-V1B18


Researcher Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.661 M Precipitate Yes but the aldehyde alone is not soluble in methanol Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp159

+


+

benzylamine

+


→

n-butyl isocyanide

21106077


+


+

furfurylamine

+


→

n-butyl isocyanide

21105579

Reaction ID UCEXP164 Researcher Emily Messner/Shannon Oseback Reaction Type Ugi Solvent methanol Limiting Reactant 0.287 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp164

+

phenylacetic acid

+

aniline

+


Reaction ID UCEXP167A-V1B12 Researcher Tim Bohinsky Reaction Type Ugi Solvent methanol Limiting Reactant 0.403 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed

405

→

n-butyl isocyanide

21106183

Reference


+


+

1-propylamine

+


→

n-butyl isocyanide

21105597

Reaction ID UCEXP173D/V2B16



+


+

methylamine

+


→

n-butyl isocyanide

21106048

Reaction ID UCEXP173G/V2B19 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

benzylamine

+


→

n-butyl isocyanide

21105845


+


+

methylamine

+


Reaction ID UCEXP174E/V2B36 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate No

406

→

n-butyl isocyanide

21106205

Comments Reference


+

Boc-Trp-OH

+

methylamine

+


→

n-butyl isocyanide

21106201

Reaction ID UCEXP174N/V2B46



+

Boc-Trp-OH

+

methylamine

+


→

n-butyl isocyanide

21106193


+


+

methylamine

+


→

n-butyl isocyanide

21106203


+


+

benzylamine

+


Reaction ID UCEXP176C Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant - M Precipitate Yes Yield 62 %

407

→

n-butyl isocyanide

21106077

Comments Reference

aldehyde not soluble until all reactants added http://usefulchem.wikispaces.com/Exp176

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594




+

phenylacetic acid

+

1-propylamine

+


→

n-butyl isocyanide

21105831


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

acetic acid

+

1-heptylamine

+



408

→

n-butyl isocyanide

21105834

+


+


+


→

n-butyl isocyanide

24528096



+


+

furfurylamine

+


→

n-butyl isocyanide

24528097


+


+

+

3-chloroaniline


→

n-butyl isocyanide

24528530


+

mandelic acid

+

furfurylamine

+



409

→

n-butyl isocyanide

24528111

+

diphenylacetic acid

+

1-propylamine

+


→

n-butyl isocyanide

24528112



+


+


+


→

n-butyl isocyanide

24528113


+


+

+

aniline

benzaldehyde

→

n-butyl isocyanide

21106208


+

mandelic acid

+

benzylamine

+



410

→

n-butyl isocyanide

24528119

+

diphenylacetic acid

+


+


→

n-butyl isocyanide

24528532



+

+

mandelic acid

methylamine

+


→

n-butyl isocyanide

24528133


+


+


+


→

n-butyl isocyanide

24528143


+

diphenylacetic acid

+

methylamine

+



411

→

n-butyl isocyanide

24528148

+

furoic acid

+

1-heptylamine

+


→

n-butyl isocyanide

21168529



+


+

benzylamine

+


→

n-butyl isocyanide

21106077


+


+

benzylamine

+


→

n-butyl isocyanide

21106077


+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

Reaction ID UCEXP225-2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.905 M Precipitate Yes Product Pending Comments 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid

412

21105594

Reference


+

Boc-Gly-OH

+

+

furfurylamine

piperonal

→

n-butyl isocyanide

24528158



+


+

+


benzaldehyde

→

n-butyl isocyanide

24528166


+


+

+

furfurylamine

piperonal

→

n-butyl isocyanide

24528174


+

Boc-Trp-OH

+

octadecylamine

+



413

→

n-butyl isocyanide

24528182

+

Boc-Trp-OH

+

octadecylamine

+


→

n-butyl isocyanide

24534188



+

Boc-Trp-OH

+

+

octadecylamine

benzaldehyde

→

n-butyl isocyanide

24534192


+

Boc-Trp-OH

+


+


→

n-butyl isocyanide

24534190


+

Boc-Trp-OH

+

1-hexylamine

+

benzaldehyde


414

→

n-butyl isocyanide

24528183

+


+


+


→

n-butyl isocyanide

21486238



+


+

furfurylamine

+

2-furaldehyde

→

n-butyl isocyanide

24528187


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

n-butyl isocyanide

24528189


+

Boc-Gly-OH

+

furfurylamine

+



415

→

n-butyl isocyanide

24528194

+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528199



+

Boc-Gly-OH

+

+

furfurylamine

crotonaldehyde

→

n-butyl isocyanide

24528203


+

Boc-Gly-OH

+

+

furfurylamine


→

n-butyl isocyanide

24528208


+

Boc-Gly-OH

+

furfurylamine

+



416

→

n-butyl isocyanide

24528213

+

Boc-Gly-OH

+

+

furfurylamine

2-furaldehyde

→

n-butyl isocyanide

24528218



+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24528223


+

Boc-Gly-OH

+

+

furfurylamine

o-tolualdehyde

→

n-butyl isocyanide

24528228


+

Boc-Gly-OH

+

furfurylamine

+



417

→

n-butyl isocyanide

24528233

+

Boc-Gly-OH

+

+

furfurylamine

hexanaldehyde

→

n-butyl isocyanide

24528238



+

Boc-Gly-OH

+

+

furfurylamine

trans-2-hexenal

→

n-butyl isocyanide

24528243


+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

24534417


+

Boc-Gly-OH

+

furfurylamine

+

m-anisaldehyde


418

→

n-butyl isocyanide

24528252

+

Boc-Gly-OH

+

+

furfurylamine


→

n-butyl isocyanide

24528257



+


+

t-butylamine

+


→

n-butyl isocyanide

24528275


+


+

3-chloroaniline

+


→

n-butyl isocyanide

24528276


+


+

benzylamine

+



419

→

n-butyl isocyanide

24528277

+

methacrylic acid

+

methylamine

+


→

n-butyl isocyanide

24528283



+


+

1-propylamine

+


→

n-butyl isocyanide

24528286


+

+


aniline

+


→

n-butyl isocyanide

24528290


+

formic acid

+

methylamine

+



420

→

n-butyl isocyanide

24528292

+

methacrylic acid

+

t-butylamine

+


→

n-butyl isocyanide

24528293



+

methacrylic acid

+

3-chloroaniline

+


→

n-butyl isocyanide

24528296


+

methacrylic acid

+

benzylamine

+


→

n-butyl isocyanide

24528297


+

phenylacetic acid

+

furfurylamine

+



421

→

n-butyl isocyanide

21105594

+

+

phenylacetic acid

furfurylamine

+


→

n-butyl isocyanide

21105594



+

+

phenylacetic acid

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+


+


→

n-butyl isocyanide

21782451


+


+

methylamine

+

veratraldehyde


422

→

n-butyl isocyanide

24528355

Reference


+


+

+

methylamine

veratraldehyde

→

n-butyl isocyanide

24528355




+


+

+


methylamine

→

n-butyl isocyanide

24528364


+


+

methylamine

+


→

n-butyl isocyanide

24528365


+


+

1-hexylamine

+



Khalid Mirza

423

→

n-butyl isocyanide

24528366


+


+

2-chloroaniline

+


→

n-butyl isocyanide

24528368



+

+


aniline

+


→

n-butyl isocyanide

24528369


+


+

1-heptylamine

+


→

n-butyl isocyanide

24528377


+

phenylacetic acid

+

furfurylamine

+


424

→

n-butyl isocyanide

21105594


+

phenylacetic acid

+


+


→

n-butyl isocyanide

24528387



+


+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528391


+


+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528391


+

+

+

425

→



piperonal

n-butyl isocyanide

24528392


+



+


+

piperonal

→

n-butyl isocyanide

24528392


+

cbz-proline

+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528399


+

cbz-proline

+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528399


+

+

+

426

→

cbz-proline


piperonal

n-butyl isocyanide

24528400



+

cbz-proline

+


+

piperonal

→

n-butyl isocyanide

24528400


+


+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528409


+


+

furfurylamine

+

piperonal


427

→

n-butyl isocyanide

24528409

Reference


+


+

+


piperonal

→

n-butyl isocyanide

24528410




+


+

+


piperonal

→

n-butyl isocyanide

24528410


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+




428

→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


429

→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

+

+

430

→

phenylacetic acid

furfurylamine


n-butyl isocyanide

21105594



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594

o-tolualdehyde Reaction ID UCEXP232-41 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.083 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde

→

t-butyl isocyanide

24528227


+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde

Reaction ID UCEXP232-43 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.083 M Precipitate No

431

→

n-butyl isocyanide

24528228

Comments Reference


+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde

→

1-pentyl isocyanide

24528229




+

Boc-Gly-OH

+

furfurylamine

+

o-tolualdehyde

→


24528230


+

Boc-Gly-OH

+

furfurylamine

+

→


o-tolualdehyde

24528231


+


+

methylamine

+

o-tolualdehyde

o-vanillin 432

→

t-butyl isocyanide

24528363


+

Boc-Trp-OH

+

1-heptylamine

+

o-vanillin

→

benzyl isocyanide

21106061



+

Boc-Trp-OH

+

1-octylamine

+

o-vanillin

→

benzyl isocyanide

21106062


+

Boc-Trp-OH

+

1-hexylamine

+

o-vanillin

→

n-butyl isocyanide

21106063


+

Boc-Trp-OH

+

1-hexylamine

+

o-vanillin


433

→

1-pentyl isocyanide

21106064


+

Boc-Trp-OH

+

1-heptylamine

+

o-vanillin

→

n-butyl isocyanide

21106065



+

Boc-Trp-OH

+

1-heptylamine

+

o-vanillin

→

1-pentyl isocyanide

21106066


+

Boc-Trp-OH

+

1-propylamine

+

o-vanillin

→

n-butyl isocyanide

21106070


+

Boc-Trp-OH

+

1-propylamine

+

o-vanillin


Rikesh Parikh Ugi

434

→

1-pentyl isocyanide

21106071


+

+

Boc-Trp-OH

1-octylamine

+

o-vanillin

→

n-butyl isocyanide

21106072




+

+

Boc-Trp-OH

1-octylamine

+

o-vanillin

→

1-pentyl isocyanide

21106073


+


+


+

o-vanillin

→

t-butyl isocyanide

21106056


+


+

benzylamine

+

o-vanillin

Reaction ID UCEXP173N/V2B26 Researcher Reaction Type Solvent


435

→

t-butyl isocyanide

21105846

Limiting Reactant 0.217 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+

decanoic acid

+

+

2-chloroaniline

o-vanillin

→


21105847




+


+

+

methylamine

o-vanillin

→


24528107

octadecylamine Reaction ID UCEXP228-1 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.253 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp228

+

Boc-Trp-OH

+

octadecylamine

+


→


24528181


+

Boc-Trp-OH

+

octadecylamine

+



Khalid Mirza

436

→

n-butyl isocyanide

24528182


+

Boc-Trp-OH

+

octadecylamine

+


→

n-butyl isocyanide

24534188



+

Boc-Trp-OH

+

+

octadecylamine

benzaldehyde

→

n-butyl isocyanide

24534192


+

Boc-Trp-OH

+

octadecylamine

+


→

t-butyl isocyanide

24534189

phenanthrene-9-carboxaldehyde Reaction ID UCEXP148A-V1B153 Researcher Khalid Mirza/ Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.398 M Precipitate Yes but the aldehyde alone is not soluble in methanol Yield 50.1 % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp148

+

crotonic acid

+

1-heptylamine

+


437

→

t-butyl isocyanide

21106058

Reaction ID UCEXP150D-V1B155 Researcher Khalid Mirza/ Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.404 M Precipitate Yes but the aldehyde alone is not soluble in methanol Yield 59 % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp150

+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601



+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21106075

Reaction ID UCEXP159C-V1B18 Researcher Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.661 M Precipitate Yes but the aldehyde alone is not soluble in methanol Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp159

+


+

benzylamine

+


→

n-butyl isocyanide

21106077


+


+

furfurylamine

+


438

→

n-butyl isocyanide

21105579


+

phenylacetic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

21105590


Reaction ID UCEXP163A-V1B14 Researcher Tim Bohinsky Reaction Type Ugi Solvent methanol Limiting Reactant 0.387 M Precipitate no and aldehyde alone not solube Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp163

+

mandelic acid

+

furfurylamine

+


→

t-butyl isocyanide

21105596

Reaction ID UCEXP164 Researcher Emily Messner/Shannon Oseback Reaction Type Ugi Solvent methanol Limiting Reactant 0.287 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp164

+

phenylacetic acid

+

aniline

+


→

n-butyl isocyanide

21106183

Reaction ID UCEXP167A-V1B12 Researcher Tim Bohinsky Reaction Type Ugi Solvent methanol Limiting Reactant 0.403 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp167

+


+

1-propylamine

+


439

→

n-butyl isocyanide

21105597


+


+

methylamine

+


→


21106040



+


+

methylamine

+


→

t-butyl isocyanide

21106039


+


+

furfurylamine

+


→

t-butyl isocyanide

21106041


+


+

methylamine

+


Reaction ID UCEXP175D

440

→

n-butyl isocyanide

21106205

Researcher Khalid Mirza/ Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.398 M Precipitate Yes but the aldehyde alone is not soluble in methanol Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp175

+

+


benzylamine

+


→

n-butyl isocyanide

21106077


Reaction ID UCEXP176C Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant - M Precipitate Yes Yield 62 % Comments aldehyde not soluble until all reactants added Reference http://usefulchem.wikispaces.com/Exp176

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

1-propylamine

+


→

n-butyl isocyanide

21105831


+

phenylacetic acid

+

furfurylamine

+



441

→

n-butyl isocyanide

21105594


+

+


aniline

+


→

t-butyl isocyanide

21105833



+

+

acetic acid

1-heptylamine

+


→

n-butyl isocyanide

21105834


+


+


+


→

n-butyl isocyanide

24528096


+


+

furfurylamine

+



Khalid Mirza

442

→

n-butyl isocyanide

24528097

Reaction Type Ugi Solvent methanol Limiting Reactant 0.218 M Precipitate no and aldehyde alone not solube Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+

mandelic acid

+

furfurylamine

+


→

n-butyl isocyanide

24528111



+


+

furfurylamine

+


→

t-butyl isocyanide

24528115


+

mandelic acid

+

methylamine

+


→

n-butyl isocyanide

24528133


+


+

methylamine

+



Khalid Mirza

443

→

t-butyl isocyanide

24528534

Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+


+


+


→

n-butyl isocyanide

24528143



+

+


furfurylamine

+


→


24528151


+

furoic acid

+

1-heptylamine

+


→

n-butyl isocyanide

21168529


+

mandelic acid

+

cyclohexylamine

+


Reaction ID UCEXP184-1/49 Researcher

Emily Messner

444

→

t-butyl isocyanide

24528153

Reaction Type Ugi Solvent ethanol Limiting Reactant 0.398 M Precipitate Reactants insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp184

+

mandelic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528154



+

mandelic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528154


+

mandelic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528154


+

crotonic acid

+

benzylamine

+


Reaction ID UCEXP215A Researcher Reaction Type

Khalid Mirza Ugi

445

→

t-butyl isocyanide

21105601


+

crotonic acid

+

1-heptylamine

+


→

t-butyl isocyanide

21106058

Reaction ID UCEXP215B



+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601


+


+

benzylamine

+


→

n-butyl isocyanide

21106077


+


+

benzylamine

+




446

→

n-butyl isocyanide

21106077


+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601



Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.384 M Precipitate Yes Product Pending Comments Reference http://usefulchem.wikispaces.com/Exp217

+

Boc-Gly-OH

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601


+

phenylacetic acid

+

furfurylamine

+




447

→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594




+

crotonic acid

+

2-chloroaniline

+


→


24528303


+

crotonic acid

+

3-chloroaniline

+


→


24528304


+

crotonic acid

+

aniline

+



448

→


24528305

Comments Reference


+

crotonic acid

+

benzylamine

+


→


24528306




+

crotonic acid

+

butylamine

+


→


24528307


+

crotonic acid

+

cyclohexylamine

+


→


24528308


+

crotonic acid

+

furfurylamine

+



449

→


24528309

+

crotonic acid

+

1-heptylamine

+


→


24528310



+

crotonic acid

+

1-hexylamine

+


→


24528311


+

crotonic acid

+

methylamine

+


→


24528312


+

crotonic acid

+

1-propylamine

+



450

→


24528313

+

crotonic acid

+

t-butylamine

+


→


24528314



+

crotonic acid

+

2-chloroaniline

+


→

t-butyl isocyanide

24528315


+

crotonic acid

+

3-chloroaniline

+


→

t-butyl isocyanide

24528316


+

crotonic acid

+

aniline

+



451

→

t-butyl isocyanide

24528317

+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601



+

crotonic acid

+

butylamine

+


→

t-butyl isocyanide

24528318


+

crotonic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528319


+

crotonic acid

+

furfurylamine

+



452

→

t-butyl isocyanide

24528320

+

crotonic acid

+

1-heptylamine

+


→

t-butyl isocyanide

21106058



+

crotonic acid

+

1-hexylamine

+


→

t-butyl isocyanide

24528321


+

crotonic acid

+

methylamine

+


→

t-butyl isocyanide

24528322


+

crotonic acid

+

1-propylamine

+



453

→

t-butyl isocyanide

24528323

+

crotonic acid

+

t-butylamine

+


→

t-butyl isocyanide

24528324



+

Boc-Gly-OH

+

2-chloroaniline

+


→


24528325


+

Boc-Gly-OH

+

3-chloroaniline

+


→


24528326


+

Boc-Gly-OH

+

aniline

+



454

→


24528327

Reference


+

Boc-Gly-OH

+

benzylamine

+


→


24528328




+

Boc-Gly-OH

+

butylamine

+


→


24528329


+

Boc-Gly-OH

+

cyclohexylamine

+


→


24528330


+

Boc-Gly-OH

+

furfurylamine

+



455

→


24528331

Reference


+

Boc-Gly-OH

+

1-heptylamine

+


→


24528332




+

Boc-Gly-OH

+

1-hexylamine

+


→


24528333


+

Boc-Gly-OH

+

methylamine

+


→


24528334


+

Boc-Gly-OH

+

1-propylamine

+


Reaction ID UCExp238-36 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.686 M Precipitate Yes but solvent evaporated

456

→


24528335

Comments Reference


+

Boc-Gly-OH

+

t-butylamine

+


→


24528336




+

Boc-Gly-OH

+

2-chloroaniline

+


→

t-butyl isocyanide

24528337


+

Boc-Gly-OH

+

3-chloroaniline

+


→

t-butyl isocyanide

24528338


+

Boc-Gly-OH

+

aniline

+



457

→

t-butyl isocyanide

24528339

Comments Reference


+

Boc-Gly-OH

+

benzylamine

+


→

t-butyl isocyanide

24528340




+

Boc-Gly-OH

+

butylamine

+


→

t-butyl isocyanide

24528341


+

Boc-Gly-OH

+

cyclohexylamine

+


→

t-butyl isocyanide

24528342


+

Boc-Gly-OH

+

furfurylamine

+



458

→

t-butyl isocyanide

24528343

Comments Reference


+

Boc-Gly-OH

+

1-heptylamine

+


→

t-butyl isocyanide

24528344



Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.607 M Precipitate Yes but after 48h Comments Reference http://usefulchem.wikispaces.com/Exp240

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

t-butyl isocyanide

21791788


+

phenylacetic acid

+

furfurylamine

+



459

→


24528345

Reference


+

+

phenylacetic acid

furfurylamine

+

→



21782583




+

+

phenylacetic acid

furfurylamine

+


→

benzyl isocyanide

24528346


+

+

phenylacetic acid

furfurylamine

+


→

1-pentyl isocyanide

24528347


+

phenylacetic acid

+


+


Reaction ID UCExp240-08 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.813 M

460

→

n-butyl isocyanide

21782451


Yes but 48h http://usefulchem.wikispaces.com/Exp240

+

phenylacetic acid

+


+


→

t-butyl isocyanide

24528348




+

phenylacetic acid

+


+


→


21782450


+

phenylacetic acid

+


+

→



24528349


+

phenylacetic acid

+


+




461

→

benzyl isocyanide

24528350

Limiting Reactant 1.776 M Precipitate Yes but 48h Comments Reference http://usefulchem.wikispaces.com/Exp240

+

phenylacetic acid

+


+


→

1-pentyl isocyanide

24528351




+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+


+


→

1-pentyl isocyanide

24528382


+

phenylacetic acid

+

furfurylamine

+


Reaction ID UCExp242-3 Researcher Marshall Moritz Reaction Type Ugi Solvent benzene Limiting Reactant 0.432 M Precipitate Yes

462

→

t-butyl isocyanide

24528383



+

phenylacetic acid

+

furfurylamine

+


→


24528384



Researcher Marshall Moritz Reaction Type Ugi Solvent benzene Limiting Reactant 0.414 M Precipitate Yes Product No Comments Reference http://usefulchem.wikispaces.com/Exp242

+

phenylacetic acid

+

furfurylamine

+

→



24528385


+

phenylacetic acid

+

furfurylamine

+


→

1-pentyl isocyanide

24528386


+

phenylacetic acid

+


+



Marshall Moritz Ugi benzene

463

→

n-butyl isocyanide

24528387


+

phenylacetic acid

+


+


→

t-butyl isocyanide

24528388




+

phenylacetic acid

+


+


→


24528389


+

phenylacetic acid

+


+

→



24528390


+

phenylacetic acid

+

furfurylamine

+



Khalid Mirza Ugi

464

→

n-butyl isocyanide

21105594

Solvent methanol Limiting Reactant 0.53 M Precipitate Yes Yield 42.6 % Comments Reference http://usefulchem.wikispaces.com/Exp253

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


465

→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

+

+

466

→

phenylacetic acid

furfurylamine


n-butyl isocyanide

21105594



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594

phenylacetic acid Reaction ID UCEXP162 Researcher Shannon Oseback Reaction Type Ugi Solvent methanol Limiting Reactant 0.285 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp162

+

phenylacetic acid

+

cyclohexylamine

+


Reaction ID UCEXP164 Researcher Emily Messner/Shannon Oseback Reaction Type Ugi Solvent methanol Limiting Reactant 0.287 M

467

→

t-butyl isocyanide

21105590


Reactants Insoluble Protocol from Explan005 followed http://usefulchem.wikispaces.com/Exp164

+

+

phenylacetic acid

aniline

+


→

n-butyl isocyanide

21106183



Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant - M Precipitate Yes Yield 62 % Comments aldehyde not soluble until all reactants added Reference http://usefulchem.wikispaces.com/Exp176

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

1-propylamine

+


→

n-butyl isocyanide

21105831


+

phenylacetic acid

+

furfurylamine

+


Reaction ID UCExp237-01 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.778 M Precipitate Yes

468

→

n-butyl isocyanide

21105594


Awaiting Characterization http://usefulchem.wikispaces.com/Exp237

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594




+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+



469

→

t-butyl isocyanide

21791788

Comments Reference


+

phenylacetic acid

+

furfurylamine

+


→


24528345




+

phenylacetic acid

+

furfurylamine

+

→



21782583


+

phenylacetic acid

+

furfurylamine

+


→

benzyl isocyanide

24528346


+

phenylacetic acid

+

furfurylamine

+


Reaction ID UCExp240-07 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.839 M

470

→

1-pentyl isocyanide

24528347


Yes - % http://usefulchem.wikispaces.com/Exp240

+

phenylacetic acid

+


+


→

n-butyl isocyanide

21782451



Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.813 M Precipitate Yes but 48h Comments Reference http://usefulchem.wikispaces.com/Exp240

+

phenylacetic acid

+


+


→

t-butyl isocyanide

24528348


+

phenylacetic acid

+


+


→


21782450


+

phenylacetic acid

+


+



Khalid Mirza Ugi

471

→


24528349


+

phenylacetic acid

+


+


→

benzyl isocyanide

24528350



Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 1.776 M Precipitate Yes but 48h Comments Reference http://usefulchem.wikispaces.com/Exp240

+

phenylacetic acid

+


+


→

1-pentyl isocyanide

24528351


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+


+


Reaction ID UCExp242-2 Researcher Marshall Moritz Reaction Type Ugi Solvent benzene Limiting Reactant 0.436 M

472

→

1-pentyl isocyanide

24528382



+

phenylacetic acid

+

furfurylamine

+


→

t-butyl isocyanide

24528383



Researcher Marshall Moritz Reaction Type Ugi Solvent benzene Limiting Reactant 0.432 M Precipitate Yes Product No Comments Reference http://usefulchem.wikispaces.com/Exp242

+

phenylacetic acid

+

furfurylamine

+


→


24528384


+

phenylacetic acid

+

furfurylamine

+

→



24528385


+

phenylacetic acid

+

furfurylamine

+



Marshall Moritz Ugi

473

→

1-pentyl isocyanide

24528386

Solvent benzene Limiting Reactant 0.431 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp242

+

phenylacetic acid

+


+


→

n-butyl isocyanide

24528387




+

phenylacetic acid

+


+


→

t-butyl isocyanide

24528388


+

phenylacetic acid

+


+


→


24528389


+

phenylacetic acid

+


+



Khalid Mirza Ugi

474

→


24528390

Solvent benzene Limiting Reactant 0.403 M Precipitate Yes Yield - % Comments Reference http://usefulchem.wikispaces.com/Exp252

+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


475

→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

+

+

476

→

phenylacetic acid

furfurylamine


n-butyl isocyanide

21105594



+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


→

n-butyl isocyanide

21105594


+

phenylacetic acid

+

furfurylamine

+


phenylpropynoic acid Reaction ID UCEXP173G/V2B19 Researcher Reaction Type Solvent


477

→

n-butyl isocyanide

21105594

Limiting Reactant 0.223 M Precipitate Yes Yield - % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+


+

benzylamine

+


→

n-butyl isocyanide

21105845



+


+

methylamine

+


→


24528098


+


+

furfurylamine

+


→


24528100


+


+

aniline

+



David Bulger

478

→


24528137


+


+

benzylamine

+


→


23078615



+


+

benzylamine

+


→

t-butyl isocyanide

24528265


+


+

benzylamine

+


→


23078615


+


+

benzylamine

+



David Bulger

479

→

t-butyl isocyanide

24528265


+


+

+


benzylamine

→

t-butyl isocyanide

24528266



+


+

+


benzylamine

→


23078614


+


+

+


benzylamine

→

t-butyl isocyanide

24528266


+


+

benzylamine

+


480

→


23078614

piperonal Reaction ID UCEXP052E Researcher Alicia Holsey Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes Yield 32 % Comments 1M solutions of the starting materials was made Reference http://usefulchem.wikispaces.com/Exp052


+

Boc-Gly-OH

+


+

piperonal

→

t-butyl isocyanide

10481872


+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528157


+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

n-butyl isocyanide


481

24528158

+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

1-pentyl isocyanide

24528159



+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→


24528160


+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

benzyl isocyanide

24528161


+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→



482

24528162

+

Boc-Gly-OH

+

furfurylamine

+

→


piperonal

24528163



+

Boc-Gly-OH

+

furfurylamine

+

→


piperonal

24528164


+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528173


+


+

furfurylamine

+

piperonal

→

n-butyl isocyanide


483

24528174

+


+

furfurylamine

+

piperonal

→

1-pentyl isocyanide

24528175



+


+

furfurylamine

+

piperonal

→


24528176


+


+

furfurylamine

+

piperonal

→

benzyl isocyanide

24528177


+


+

furfurylamine

+

piperonal

→



484

24528178

+


+

furfurylamine

+

→


piperonal

24528179



+


+

furfurylamine

+

→


piperonal

24528180


+


+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528391


+


+

furfurylamine

+

piperonal



485

→

n-butyl isocyanide

24528391


+


+


+

piperonal

→

n-butyl isocyanide

24528392



+


+


+

piperonal

→

n-butyl isocyanide

24528392


+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528393


+


+

furfurylamine

+

piperonal

486

→

t-butyl isocyanide

24528393


+


+

furfurylamine

+

piperonal

→


24528394



+


+

furfurylamine

+

piperonal

→


24528394


+


+

furfurylamine

+

→


piperonal

24528395


+

+

+

487

→


furfurylamine


piperonal

24528395




+


+


+

piperonal

→

t-butyl isocyanide

24528396


+


+


+

piperonal

→

t-butyl isocyanide

24528396


+


+


+

piperonal


Khalid Mirza Ugi

488

→


24528397


+


+


+

piperonal

→


24528397



+


+


+

→


piperonal

24528398


+


+


+

→


piperonal

24528398


+

cbz-proline

+

furfurylamine

+

piperonal

489

→

n-butyl isocyanide

24528399


+

cbz-proline

+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528399



+

cbz-proline

+


+

piperonal

→

n-butyl isocyanide

24528400


+

cbz-proline

+


+

piperonal

→

n-butyl isocyanide

24528400


+

cbz-proline

+

furfurylamine

+

piperonal


490

→

t-butyl isocyanide

24528401


+

cbz-proline

+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528401



+

cbz-proline

+

furfurylamine

+

piperonal

→


24528402


+

cbz-proline

+

furfurylamine

+

piperonal

→


24528402


+

cbz-proline

+

furfurylamine

+

piperonal


491

→


24528403


+

cbz-proline

+

furfurylamine

+

→


piperonal

24528403



+

cbz-proline

+


+

piperonal

→

t-butyl isocyanide

24528404


+

cbz-proline

+


+

piperonal

→

t-butyl isocyanide

24528404


+

cbz-proline

+


+

piperonal

492

→


24528405


+

cbz-proline

+


+

→


piperonal

24528405



+

cbz-proline

+


+

piperonal

→


24528406


+

cbz-proline

+


+

piperonal

→


24528406


+


+

furfurylamine

+

piperonal

493

→

t-butyl isocyanide

24528407


+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528407



+


+

furfurylamine

+

→


piperonal

24528408


+


+

furfurylamine

+

→


piperonal

24528408


+

+

+

494

→


furfurylamine

piperonal

n-butyl isocyanide

24528409




+


+

furfurylamine

+

piperonal

→

n-butyl isocyanide

24528409


+


+


+

piperonal

→

n-butyl isocyanide

24528410


+


+


+

piperonal

salicylic acid 495

→

n-butyl isocyanide

24528410


+

salicylic acid

+


+


→


21106076

t-butyl isocyanide Nature Precedings : doi:10.1038/npre.2010.4416.1 : Posted 4 May 2010

Reaction ID UCEXP052E Researcher Alicia Holsey Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate Yes Yield 32 % Comments 1M solutions of the starting materials was made Reference http://usefulchem.wikispaces.com/Exp052

+

Boc-Gly-OH

+


+

piperonal

→

t-butyl isocyanide

10481872


+

Boc-Gly-OH

+


+

benzaldehyde


496

→

t-butyl isocyanide

10481766

+

Boc-Gly-OH

+

+

furfurylamine

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

+

furfurylamine

veratraldehyde

→

t-butyl isocyanide

21106057


+


+

methylamine

+

2-naphthaldehyde

→

t-butyl isocyanide

21105841

Reaction ID UCEXP148A-V1B153 Researcher Khalid Mirza/ Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.398 M Precipitate Yes but the aldehyde alone is not soluble in methanol Yield 50.1 % Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp148

+

crotonic acid

+

1-heptylamine

+


Reaction ID UCEXP150D-V1B155 Researcher Khalid Mirza/ Emily Messner Reaction Type Ugi Solvent methanol Limiting Reactant 0.404 M Precipitate Yes but the aldehyde alone is not soluble in methanol Yield 59 % Comments Protocol from Explan005 followed

497

→

t-butyl isocyanide

21106058

Reference


+

+

crotonic acid

benzylamine

+


→

t-butyl isocyanide

21105601



+


+

+


benzaldehyde

→

t-butyl isocyanide

21106074


+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21106075


+

phenylacetic acid

+

cyclohexylamine

+


Reaction ID UCEXP163A-V1B14 Researcher Tim Bohinsky Reaction Type Ugi Solvent methanol Limiting Reactant 0.387 M Precipitate no and aldehyde alone not solube Comments Protocol from Explan005 followed

498

→

t-butyl isocyanide

21105590

Reference


+

+

mandelic acid

furfurylamine

+


→

t-butyl isocyanide

21105596



+


+


+

o-vanillin

→

t-butyl isocyanide

21106056


+


+

benzylamine

+

o-vanillin

→

t-butyl isocyanide

21105846


+


+

methylamine

+

2-naphthaldehyde

Reaction ID UCEXP171KV2B11 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.222 M Precipitate Yes Yield - %

499

→

t-butyl isocyanide

21105841

Comments Reference


+


+

methylamine

+


→

t-butyl isocyanide

21105842

Reaction ID UCEXP171LV2B-12



+


+

methylamine

+


→

t-butyl isocyanide

21106039


+


+

+

methylamine


→

t-butyl isocyanide

21105844


+


+

methylamine

+


Reaction ID UCEXP173E/V2B17 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.223 M Precipitate No Comments Protocol from Explan005 followed

500

→

t-butyl isocyanide

21106044

Reference


+

Boc-Trp-OH

+

methylamine

+


→

t-butyl isocyanide

21106045



+


+

furfurylamine

+


→

t-butyl isocyanide

21106041


+


+

methylamine

+


→

t-butyl isocyanide

21106038


+


+

methylamine

+



501

→

t-butyl isocyanide

21106050

+

D-(−)-Quinic acid

+


+


→

t-butyl isocyanide

21106186



+


+

aniline

+


→

t-butyl isocyanide

21105833


+

D-(−)-Quinic acid

+

benzylamine

+


→

t-butyl isocyanide

24528104


+

Boc-Trp-OH

+

methylamine

+

benzaldehyde


502

→

t-butyl isocyanide

24528109

+


+

aniline

+


→

t-butyl isocyanide

24528110



+


+

1-hexylamine

+


→

t-butyl isocyanide

24528114


+


+

furfurylamine

+


→

t-butyl isocyanide

24528115


+


+

2-chloroaniline

+

2-naphthaldehyde


503

→

t-butyl isocyanide

24528117

+


+

methylamine

+


→

t-butyl isocyanide

21106206



+


+

methylamine

+


→

t-butyl isocyanide

24528534


+


+

+

3-chloroaniline

2-naphthaldehyde

→

t-butyl isocyanide

24528144


+

mandelic acid

+

cyclohexylamine

+


Reaction ID UCEXP184-1/49 Researcher Emily Messner Reaction Type Ugi Solvent ethanol Limiting Reactant 0.398 M Precipitate Reactants insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp184

504

→

t-butyl isocyanide

24528153

+

mandelic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528154



+

mandelic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528154


+

mandelic acid

+

cyclohexylamine

+


→

t-butyl isocyanide

24528154


+

methacrylic acid

+


+



505

→

t-butyl isocyanide

21111670

+

methacrylic acid

+

benzylamine

+


→

t-butyl isocyanide

21111671



+

methacrylic acid

+


+


→

t-butyl isocyanide

21111670


+

methacrylic acid

+

benzylamine

+


→

t-butyl isocyanide

21111671


+

methacrylic acid

+

t-butylamine

+



506

→

t-butyl isocyanide

21143155

+

methacrylic acid

+


+


→

t-butyl isocyanide

21111670



+

methacrylic acid

+

benzylamine

+


→

t-butyl isocyanide

21111671


+

methacrylic acid

+

t-butylamine

+


→

t-butyl isocyanide

21143155


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


507

→

t-butyl isocyanide

21106059

+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


508

→

t-butyl isocyanide

21106059

Comments Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059




+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


509

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

510

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

511

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


512

→

t-butyl isocyanide

21106059

Comments Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059




+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


513

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

514

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

515

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


516

→

t-butyl isocyanide

21106059

Comments Reference


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059




+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde


517

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

518

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

+

519

→

Boc-Gly-OH

furfurylamine

benzaldehyde

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

+

furfurylamine

benzaldehyde

→

t-butyl isocyanide

21106059


+

+

crotonic acid

benzylamine

+


→

t-butyl isocyanide

21105601

Reaction ID UCEXP215A Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.661 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp215

+

crotonic acid

+

1-heptylamine

+


Reaction ID UCEXP215B Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.678 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp215

520

→

t-butyl isocyanide

21106058

+

+

crotonic acid

benzylamine

+


→

t-butyl isocyanide

21105601



+


+

+

methylamine

2-naphthaldehyde

→

t-butyl isocyanide

21105841

Reaction ID UCEXP215D Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.66 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp215

+


+

methylamine

+


→

t-butyl isocyanide

21105842


+


+

methylamine

+



521

→

t-butyl isocyanide

24528155

+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601



+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

furfurylamine

+

benzaldehyde

Reaction ID UCEXP222-2 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.898 M Precipitate Yes Yield - %

522

→

t-butyl isocyanide

21106059

Comments Reference


+

Boc-Gly-OH

+

+

furfurylamine

benzaldehyde

→

t-butyl isocyanide

21106059



Researcher Khalid Mirza Reaction Type Ugi Solvent DMSO Limiting Reactant 0.473 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp222

+

Boc-Gly-OH

+

+

furfurylamine

benzaldehyde

→

t-butyl isocyanide

21106059


+

Boc-Gly-OH

+

+

furfurylamine

benzaldehyde

→

t-butyl isocyanide

21106059


+


+

methylamine

+


Reaction ID UCEXP222-6 Researcher Khalid Mirza Reaction Type Ugi Solvent THF Limiting Reactant 0.898 M Precipitate No Comments -

523

→

t-butyl isocyanide

21105842

Reference


+


+

methylamine

+


→

t-butyl isocyanide

21105844



Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.631 M Precipitate Yes Yield - % Comments 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid Reference http://usefulchem.wikispaces.com/Exp225

+

Boc-Gly-OH

+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528157


+


+


+

benzaldehyde

→

t-butyl isocyanide

24528165


+


+

furfurylamine

+

piperonal


524

→

t-butyl isocyanide

24528173

+


+

+

methylamine


→

t-butyl isocyanide

21105844



+

Boc-Trp-OH

+

+

octadecylamine


→

t-butyl isocyanide

24534189


+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601


+


+

methylamine

+

2-naphthaldehyde


525

→

t-butyl isocyanide

21105841

+

Boc-Gly-OH

+

+

furfurylamine

benzaldehyde

→

t-butyl isocyanide

21106059



+

Boc-Gly-OH

+

+

furfurylamine


→

t-butyl isocyanide

24528193


+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528198


+

Boc-Gly-OH

+

furfurylamine

+

crotonaldehyde


526

→

t-butyl isocyanide

24528202

+

Boc-Gly-OH

+

+

furfurylamine


→

t-butyl isocyanide

24528207



+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528212


+

Boc-Gly-OH

+

+

furfurylamine

2-furaldehyde

→

t-butyl isocyanide

24528217


+

Boc-Gly-OH

+

furfurylamine

+



527

→

t-butyl isocyanide

24528222

+

Boc-Gly-OH

+

+

furfurylamine

o-tolualdehyde

→

t-butyl isocyanide

24528227



+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528232


+

Boc-Gly-OH

+

furfurylamine

+

hexanaldehyde

→

t-butyl isocyanide

24528237


+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal


528

→

t-butyl isocyanide

24528242

+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24534409



+

Boc-Gly-OH

+

+

furfurylamine

m-anisaldehyde

→

t-butyl isocyanide

24528251


+

Boc-Gly-OH

+

+

furfurylamine


→

t-butyl isocyanide

24528256


+


+

benzylamine

+



529

→

t-butyl isocyanide

24534439

+

Boc-Pro-OH

+

benzylamine

+


→

t-butyl isocyanide

24528262



+


+

benzylamine

+


→

t-butyl isocyanide

24528265


+

Boc-Pro-OH

+

benzylamine

+


→

t-butyl isocyanide

24528262


+


+

benzylamine

+



530

→

t-butyl isocyanide

24534439

+


+

benzylamine

+


→

t-butyl isocyanide

24528265



+


+

+


benzylamine

→

t-butyl isocyanide

24528266


+

+


Boc-L-Threonine

+


→

t-butyl isocyanide

24528268


+


+

benzylamine

+



531

→

t-butyl isocyanide

24528266

+

+

Fmoc-Diglycine

benzylamine

+


→

t-butyl isocyanide

24528270



+

+

Boc-diglycine

benzylamine

+


→

t-butyl isocyanide

24528272


+

+

Boc-L-Serine

benzylamine

+


→

t-butyl isocyanide

24528274


+

Boc-Gly-OH

+

furfurylamine

+



532

→

t-butyl isocyanide

24528198

+

methacrylic acid

+

butylamine

+


→

t-butyl isocyanide

24528278



+

formic acid

+

t-butylamine

+


→

t-butyl isocyanide

24528279


+


+

1-hexylamine

+


→

t-butyl isocyanide

24528280


+

formic acid

+

3-chloroaniline

+



533

→

t-butyl isocyanide

24528281

+


+

2-chloroaniline

+


→

t-butyl isocyanide

24528282



+

formic acid

+

benzylamine

+


→

t-butyl isocyanide

24528284


+

+

methacrylic acid

aniline

+


→

t-butyl isocyanide

24528285


+


+

methylamine

+



534

→

t-butyl isocyanide

24528287

+


+

1-heptylamine

+


→

t-butyl isocyanide

24528288



+

formic acid

+

butylamine

+


→

t-butyl isocyanide

24528289


+


+

methylamine

+


→

t-butyl isocyanide

24528291


+

formic acid

+

aniline

+



535

→

t-butyl isocyanide

24528294

+


+

+


t-butylamine

→

t-butyl isocyanide

24528295



+


+

+


3-chloroaniline

→

t-butyl isocyanide

24528298


+


+

+


benzylamine

→

t-butyl isocyanide

24528299


+


+

t-butylamine

+



536

→

t-butyl isocyanide

24528300

+

methacrylic acid

+

1-hexylamine

+


→

t-butyl isocyanide

24528301



+


+

cyclohexylamine

+


→

t-butyl isocyanide

24528302


+

crotonic acid

+

2-chloroaniline

+


→

t-butyl isocyanide

24528315


+

crotonic acid

+

3-chloroaniline

+



537

→

t-butyl isocyanide

24528316

+

+

crotonic acid

aniline

+


→

t-butyl isocyanide

24528317



+

crotonic acid

+

benzylamine

+


→

t-butyl isocyanide

21105601


+

crotonic acid

+

butylamine

+


→

t-butyl isocyanide

24528318


+

crotonic acid

+

cyclohexylamine

+



538

→

t-butyl isocyanide

24528319

+

crotonic acid

+

furfurylamine

+


→

t-butyl isocyanide

24528320



+

crotonic acid

+

1-heptylamine

+


→

t-butyl isocyanide

21106058


+

crotonic acid

+

1-hexylamine

+


→

t-butyl isocyanide

24528321


+

crotonic acid

+

methylamine

+



539

→

t-butyl isocyanide

24528322

+

crotonic acid

+

1-propylamine

+


→

t-butyl isocyanide

24528323



+

crotonic acid

+

t-butylamine

+


→

t-butyl isocyanide

24528324


+

Boc-Gly-OH

+

2-chloroaniline

+


→

t-butyl isocyanide

24528337


+

Boc-Gly-OH

+

3-chloroaniline

+



540

→

t-butyl isocyanide

24528338

+

+

Boc-Gly-OH

aniline

+


→

t-butyl isocyanide

24528339



+

Boc-Gly-OH

+

benzylamine

+


→

t-butyl isocyanide

24528340


+

Boc-Gly-OH

+

butylamine

+


→

t-butyl isocyanide

24528341


+

Boc-Gly-OH

+

cyclohexylamine

+



541

→

t-butyl isocyanide

24528342

+

Boc-Gly-OH

+

furfurylamine

+


→

t-butyl isocyanide

24528343



+

Boc-Gly-OH

+

1-heptylamine

+


→

t-butyl isocyanide

24528344


+

phenylacetic acid

+

furfurylamine

+


→

t-butyl isocyanide

21791788


+

phenylacetic acid

+


+



542

→

t-butyl isocyanide

24528348

+


+

+

methylamine

veratraldehyde

→

t-butyl isocyanide

24528356




+


+

+

methylamine

veratraldehyde

→

t-butyl isocyanide

24528356


+


+

+


methylamine

→

t-butyl isocyanide

24528360


+


+

methylamine

+



Khalid Mirza Ugi

543

→

t-butyl isocyanide

24528361


+


+

+

methylamine


→

t-butyl isocyanide

24528362



+


+

+

methylamine

o-tolualdehyde

→

t-butyl isocyanide

24528363


+


+

+


butylamine

→

t-butyl isocyanide

24528367


+


+

3-chloroaniline

+


544

→

t-butyl isocyanide

24528370


+


+

t-butylamine

+


→

t-butyl isocyanide

24528371



+


+

cyclohexylamine

+


→

t-butyl isocyanide

24528373


+


+

+


aniline

→

t-butyl isocyanide

24528374


+

+

+

545

→


1-propylamine


t-butyl isocyanide

24528375




+


+

furfurylamine

+


→

t-butyl isocyanide

24528376


+


+

+


t-butylamine

→

t-butyl isocyanide

24528378


+


+

3-chloroaniline

+



Khalid Mirza Ugi

546

→

t-butyl isocyanide

24528379


+

+


1-heptylamine

+


→

t-butyl isocyanide

24528380



+

+


benzylamine

+


→

t-butyl isocyanide

24528381


+

+

phenylacetic acid

furfurylamine

+


→

t-butyl isocyanide

24528383


+

phenylacetic acid

+


+



Khalid Mirza

547

→

t-butyl isocyanide

24528388


+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528393



+


+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528393


+


+


+

piperonal

→

t-butyl isocyanide

24528396


+

3,4methylenedioxyphenylacetic

+


+

piperonal

548

→

t-butyl isocyanide

24528396

acid


+

cbz-proline

+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528401



+

cbz-proline

+

furfurylamine

+

piperonal

→

t-butyl isocyanide

24528401


+

cbz-proline

+


+

piperonal

→

t-butyl isocyanide

24528404


+

cbz-proline

+


+

piperonal

549

→

t-butyl isocyanide

24528404


+


+

+

furfurylamine

piperonal

→

t-butyl isocyanide

24528407



+


+

+

furfurylamine

piperonal

→

t-butyl isocyanide

24528407

t-butylamine Reaction ID UCEXP181-105V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+


+

t-butylamine

+


→


24528135


+

+

+

550

→

methacrylic acid

t-butylamine


t-butyl isocyanide

21143155



+

methacrylic acid

+

t-butylamine

+


→

t-butyl isocyanide

21143155


+


+

t-butylamine

+


→

n-butyl isocyanide

24528275


+

formic acid

+

t-butylamine

+



551

→

t-butyl isocyanide

24528279

+

methacrylic acid

+

t-butylamine

+


→

n-butyl isocyanide

24528293



+


+

+


t-butylamine

→

t-butyl isocyanide

24528295


+


+

t-butylamine

+


→

t-butyl isocyanide

24528300


+

crotonic acid

+

t-butylamine

+



552

→


24528314

+

crotonic acid

+

t-butylamine

+


→

t-butyl isocyanide

24528324



+

Boc-Gly-OH

+

t-butylamine

+


→


24528336


+


+

t-butylamine

+


→

t-butyl isocyanide

24528371


+


+

t-butylamine

+


tosylmethyl isocyanide Reaction ID UCEXP130-3 Researcher Reaction Type Solvent


553

→

t-butyl isocyanide

24528378


+

formic acid

+

+


benzaldehyde

→


21106060

Reaction ID UCEXP147-1V2B1


Researcher Mitesh Shah Reaction Type Ugi Solvent methanol Limiting Reactant 0.659 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp147

+

+


methylamine

+


→


21105839

Reaction ID UCEXP151-1V2B10 Researcher Mitesh Shah Reaction Type Ugi Solvent methanol Limiting Reactant 0.694 M Precipitate No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp151

+

+


methylamine

+


→


21106049


+

salicylic acid

+


+


Reaction ID UCEXP171A/V2B1 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M

554

→


21106076


Yes Impurities found Protocol from Explan005 followed http://usefulchem.wikispaces.com/Exp171

+


+

methylamine

+


→


21105839

Reaction ID UCEXP171C/V2B3



+


+

methylamine

+


→


21106040


+


+

3-chloroaniline

+


→


21106047


+


+

furfurylamine

+

2-naphthaldehyde

Reaction ID UCEXP171HV2B8 Researcher Reaction Type

Khalid Mirza Ugi

555

→


21106054

Solvent methanol Limiting Reactant 0.223 M Precipitate Yes Product No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp171

+


+

methylamine

+


→


21105832



+


+

aniline

+


→


21106055


+


+

methylamine

+


→


21106049


+


+

aniline

+


Reaction ID UCEXP173H/V2B20

556

→


21106046


+


+

+


2-naphthaldehyde

→


21106053



+


+

methylamine

+


→


21106052


+


+

furfurylamine

+


→


21106051


+


+

furfurylamine

+


557

→


21106043

Reaction ID UCEXP173N/V2B26 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.217 M Precipitate Reactants Insoluble Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp173

+

decanoic acid

+

2-chloroaniline

+

o-vanillin

→


21105847



+


+

furfurylamine

+

benzaldehyde

→


21105843


+


+

furfurylamine

+


→


21106042


+

3,4-dihydroxyphenylacetic

+


+

benzaldehyde

558

→


21106189

acid


+


+

furfurylamine

+


→


21106204



+

benzoic acid

+

furfurylamine

+


→


21106202


+


+

methylamine

+

veratraldehyde

→


21106200


+

+

+

559

→


1-propylamine



21106199


+


+

+

methylamine

2-naphthaldehyde

→


21106188



+

methacrylic acid

+

aniline

+


→


21106198


+


+


+


→


21106197


+

+

+

560

→


methylamine



21106195



+


+

3-chloroaniline

+


→


21106194


+


+


+


→


21106192


+

butyric acid

+

3-chloroaniline

+



561

→


21106191

+

mandelic acid

+

3-chloroaniline

+


→


21106190



+


+

aniline

+


→


21106185


+


+

furfurylamine

+


→


21106187


+


+

methylamine

+



562

→


24528098

+


+

+

methylamine


→


24528099



+


+

furfurylamine

+


→


24528100


+


+

methylamine

+


→


24528101


+


+

1-propylamine

+



563

→


24528102

+


+

1-hexylamine

+


→


24528103



+


+

methylamine

+


→


24528105


+


+

furfurylamine

+


→


24528106


+


+

methylamine

+

o-vanillin


564

→


24528107

+


+

+

aniline

2-naphthaldehyde

→


24528108



Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate Yes Product No Comments Protocol from Explan005 followed Reference http://usefulchem.wikispaces.com/Exp181

+

mandelic acid

+

+

benzylamine

benzaldehyde

→


24528531


+


+

methylamine

+


→


21106207


+


+

aniline

+


Reaction ID UCEXP181-082V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.221 M Precipitate No

565

→


24528116

Comments Reference


+


+

furfurylamine

+


→


24528118




+


+

3-chloroaniline

+


→


24528120


+


+

methylamine

+


→


24528121


+

hexanoic acid

+

3-chloroaniline

+


Reaction ID UCEXP181-090V2 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 0.226 M Precipitate Reactants Insoluble

566

→


24528122

Comments Reference


+

4-nitrobenzoic acid

+

methylamine

+


→


24528123




+

decanoic acid

+

2-chloroaniline

+


→


24528124


+

hexanoic acid

+

aniline

+


→


24528125


+


+

furfurylamine

+



567

→


24528126

Reference


+


+

methylamine

+


→


24528127



+


+

furfurylamine

+


→


24528128


+


+

methylamine

+


→


24528129


+


+

2-chloroaniline

+



568

→


24528130

+

D-(−)-Quinic acid

+

+

methylamine


→


24528131



+


+

methylamine

+


→


24528132


+


+


+


→


24528533


+

D-(−)-Quinic acid

+

methylamine

+



569

→


24528134

+


+

t-butylamine

+


→


24528135



+


+

+

methylamine

2-naphthaldehyde

→


24528136


+


+

aniline

+


→


24528137


+

D-(−)-Quinic acid

+

methylamine

+

2-naphthaldehyde


570

→


24528138

+


+

1-hexylamine

+


→


24528139



+


+

aniline

+


→


24528140


+


+

methylamine

+


→


24528141


+


+

3-chloroaniline

+

veratraldehyde


571

→


24528142

+


+

+

methylamine


→


24528145



+


+

+

furfurylamine

veratraldehyde

→


24534442


+


+

+


methylamine

→


24528147


+


+

methylamine

+



572

→


24528149

+


+

3-chloroaniline

+


→


24528150



+


+

+

2-chloroaniline

veratraldehyde

→


24534443


+


+

furfurylamine

+


→


24528151


+


+

benzylamine

+


→


Reaction ID UCEXP225-6 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.438 M Precipitate No Comments 0.5 mmol of isocyanide was added to 500uL of a 2M solution of aldehyde; amine and acid

573

24528152

Reference


+

Boc-Gly-OH

+

+

furfurylamine

piperonal

→


24528162



+


+

+


benzaldehyde

→


24528170


+


+

+

furfurylamine

piperonal

→


24528178


+

Boc-Trp-OH

+

octadecylamine

+



574

→


24528181

+

Boc-Trp-OH

+


+


→


24534191



+

formic acid

+

+

benzylamine


→


24528186


+

glycolic acid

+

1-heptylamine

+


→


24528188

trans-2-hexenal Reaction ID UCEXP232-56 Researcher Khalid Mirza Reaction Type Ugi Solvent methanol Limiting Reactant 1.109 M Precipitate No Comments Reference http://usefulchem.wikispaces.com/Exp232

+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal


575

→

t-butyl isocyanide

24528242

Reference


+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal

→

n-butyl isocyanide

24528243



+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal

→

1-pentyl isocyanide

24528243


+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal

→


24528244


+

Boc-Gly-OH

+

furfurylamine

+

trans-2-hexenal

veratraldehyde Reaction ID UCEXP064C Researcher Reaction Type Solvent


576

→


24528245

Limiting Reactant 0.393 M Precipitate Yes Yield 43.8 % Comments Solution was made up to 4 mL - methanol amount probably closer to 3 mL Reference http://usefulchem.wikispaces.com/Exp064

+

Boc-Gly-OH

+


+

veratraldehyde

→

benzyl isocyanide

10481870



+

Boc-Gly-OH

+

furfurylamine

+

veratraldehyde

→

t-butyl isocyanide

21106057


+

Boc-Trp-OH

+

furfurylamine

+

veratraldehyde

→

n-butyl isocyanide

21106067


+

Boc-Trp-OH

+

furfurylamine

+

veratraldehyde


577

→

1-pentyl isocyanide

21106068


+

Boc-Trp-OH

+


+

veratraldehyde

→

1-pentyl isocyanide

21106069



+


+

methylamine

+

veratraldehyde

→


21106200


+


+

3-chloroaniline

+

veratraldehyde

→


24528142


+


+

furfurylamine


+

veratraldehyde

578

→


24534442


+


+

2-chloroaniline

+

veratraldehyde

→


24534443



+


+

methylamine

+

veratraldehyde

→

n-butyl isocyanide

24528355


+


+

methylamine

+

veratraldehyde

→

n-butyl isocyanide

24528355


+

3,4methylenedioxyphenylacetic

+

methylamine

+

veratraldehyde

579

→

t-butyl isocyanide

24528356

acid


+


+

methylamine

+

veratraldehyde

→

t-butyl isocyanide

24528356



+


+

methylamine

+

veratraldehyde

→


21782465


+


+

methylamine

+

veratraldehyde


580

→


21782465

+


+

methylamine

+

→


veratraldehyde

24528357




+


+

methylamine

+

→


veratraldehyde

24528357


+


+

methylamine

+

veratraldehyde

→

1-pentyl isocyanide

24528358


+


+

methylamine

+

veratraldehyde


Khalid Mirza Ugi

581

→

1-pentyl isocyanide

24528358


+


+

methylamine

+

veratraldehyde

→

benzyl isocyanide

24528359



+


+

methylamine

+

veratraldehyde

→

benzyl isocyanide

24528359


+


+

methylamine

+

veratraldehyde

582

→

benzyl isocyanide

24528359