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Double-Oxidative Dehydrogenative (DOD) Cyclization of Glycine Derivatives with Dioxane under Metal-Free Aerobic Conditions Congde Huo,a,* Haisheng Xie,a Fengjuan Chen,a Jing Tang,a and Yajun Wanga a

Key Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education; College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, PeopleÏs Republic of China Fax: (+ + 86)-931-797-1989; e-mail: [email protected] or [email protected]

Received: September 24, 2015; Revised: December 4, 2015; Published online: February 15, 2016 Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201500893. Abstract: The first carbon tetrabromide-promoted novel double-oxidative dehydrogenative cyclization/ acidic ring opening/aromatization tandem reaction of glycine derivatives with dioxane for the synthesis of complex quinoline motifs has been developed (up to 71% yield). The use of very inexpensive substrates (glycine derivatives and dioxane) and an extremely simple metal-free promoter (carbon tetrabromide) with green molecular oxygen (air) as an oxidant make this protocol very attractive for potential synthetic applications. A plausible mechanism involving a radical process is proposed.

tool in heterocyclic synthetic chemistry (Scheme 1, A).[7]

Keywords: aerobic conditions; carbon tetrabromide (CBr4); dioxane; glycine derivatives; oxidative coupling

The oxidative cross-dehydrogenative coupling (CDC) reaction has become a growing and very attractive field within the requirements of green chemistry.[1] Especially, metal-free CDC reactions have gained significant notice recently because the use of non-metallic reagents instead of transition metal catalysts has a number of advantages such as low cost and easy handling.[2–4] Peroxides,[2] quinones[3] and hypervalent iodine reagents[4] were the most widely used chemical oxidants in the metal-free CDC reactions. However, molecular oxygen as the terminal oxidant has been of long-standing interest when taking atom economy and sustainable development into account.[5] The formal [4+ +2] cyclization of imines derived from aromatic amines and electron-rich olefins to form tetrahydroquinoline motifs is known as the Povarov reaction.[6] Since its discovery in the 1960s, the Povarov reaction has become an powerful synthetic 724

Scheme 1. Design of the double-oxidative dehydrogenative (DOD) cyclization.

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Double-Oxidative Dehydrogenative (DOD) Cyclization of Glycine Derivatives

Li et al. reported the first example of oxidative C¢ H functionalization of glycine derivatives in 2008.[8] After that, interesting progress has been achieved in this area.[9] Among these developments, the oxidative Povarov/aromatization tandem reaction of glycine derivatives with electron-rich alkenes was first reported by MancheÇo et al. in 2011.[9l] Very recently, we for the first time discovered that the same tandem process can be promoted by the very simple, metal-free reagent carbon tetrabromide (CBr4) under aerobic conditions.[9e] CBr4 was reported for the first time to show good reactivity for CDC reactions. The mechanism involving the oxidation of secondary amines to

imines was generally proposed for the above reactions of glycine derivatives (Scheme 1, B). Otherwise, through an overall literature research, we found that dioxane, a saturated cyclic ether and commonly used solvent, could donate two hydrogen atoms to a hydrogen acceptor to give dioxene in occasional cases (Scheme 1, C).[10] From a scientific point of view, a double-oxidative dehydrogenative (DOD) cyclization reaction from 4 C¢H bonds would be highly desired (Scheme 1, general idea). As a beginning, we became interested in determining whether it is possible to oxidize the glycine derivative (to generate an arylimine) and diox-

Table 1. Screening of the reaction conditions.

[a] [b] [c]

Reaction conditions: 1t (1 mmol), 2 (50 equiv.), 13 h. Yields of the isolated product. The main by-product in this transformation is ethyl (2-bromo-4-methylphenyl)glycylglycinate, which can be isolated in 12% yield under the optimized reaction conditions. DBE = dibromoethane, NBS = N-bromosuccinimide, DBDMH = 1,3-dibromo-5,5-dimethylhydantoin.

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ane (to generate an electron-rich alkene) in the same reaction mixture, thus, with the following imino Diels–Alder procedure, possibly offering an interesting opportunity for new types of cyclization reaction (Scheme 1, D). Herein we report the preliminary realization of the above idea and demonstrate that it is possible to carry out the double-oxidative dehydrogenative (DOD) cyclization of glycine derivatives with dioxane under novel, metal- and solvent-free CBr4-mediated aerobic conditions (Scheme 1, E). This primary work illustrates the great application potential of the DOD

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cyclization to construct multiple carbon-carbon bonds and deliver complex cyclic frameworks. As shown in Table 1, our initial efforts focused on the reaction of glycylglycine derivative 1t (a dipeptide) and dioxane 2 using CBr4 as the promoter and air as the terminal oxidant. To our delight, when the mixture was heated at 80 8C for 13 h, the desired product 3t was detected. The highest yield was obtained when 15 mol% of CBr4 was used (Table 1, entry 2). The structure of 3t was confirmed by the Xray diffraction.[11] Subsequently, triphenylphosphine (PPh3) was chosen as an additive. Fortunately, in the

Table 2. Catalytic amounts of CBr4-promoted aerobic double-oxidative dehydrogenative (DOD) cyclization reaction of glycine esters with dioxane.

[a] [b] [c]

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Reaction conditions: 1 (1 mmol), 2 (50 equiv.), CBr4 (15 mol%), PPh3 (15 mol%), air, 80 8C. Yield of the isolated product. Gram scale reaction. asc.wiley-vch.de

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Double-Oxidative Dehydrogenative (DOD) Cyclization of Glycine Derivatives

presence of 15 mol% PPh3, the yield of 3t dramatically increased to 71% (Table 1, entry 5). No peptide degradation has been observed with these conditions and the reaction occurred exclusively at the N terminus of the dipeptide. No appreciable differences of the transformation were observed when pure dioxygen was used instead of an air atmosphere (Table 1, entry 10). Both increasing and decreasing the temperature resulted in lower yields (Table 1, entries 11 and 12). The effect of different bromine sources such as NBS, DBDMH, DBE, CHBr3 and CH2Br2 was surveyed too, no better yields than that with CBr4 were observed (Table 1, entries 13–17). Finally, control reactions demonstrated that no yield of the final product 3t was obtained in the absence of CBr4 (Table 1, entries 18 and 19). All together it was discovered that CBr4 (15 mol%)/PPh3 (15 mol%) at 80 8C were the optimized reaction conditions (71%, Table 1, entry 5). With the optimized reaction conditions established, we next explored the substrate scope of this CBr4-promoted double-oxidative dehydrogenative (DOD) cyclization/acidic ring opening/aromatization tandem reaction. Various glycine derivatives were investigated in dioxane under the standard conditions. Different glycine amides (R = NH-Me, NH-Et, NH-t-Bu, pyrrolidinyl) were tested and proved to give the corresponding products in good yields (Table 2, 3a–3d). Secondary and tertiary amides all reacted well. Arylglycine amides with electron-rich substituents or electron-poor substituents, as well as the para-, meta-, and ortho- substituent groups on the aryl ring all gave the desired quinolines in satisfactory yields (Table 2, 3e– 3p). Halogen substituents were well tolerated (Table 2, 3r, 3s). This makes the methodology more useful for further transformations. In addition, substrates bearing multiple substituents also worked well (Table 2, 3m–3p). Under the same reaction conditions, various glycine esters were effective substrates in this system too (Table 2, 3q–3s). It is worth noting that glycine dipeptide 1t and tripeptide 1u also gave good yields of the desired quinolines (Table 2, 3t, 3u). To evaluate the practicability of this method, the reaction between dipeptide 1t and dioxane has been performed on a gram scale in a single batch. No obvious loss of yield was observed (isolated yield: 65%). To gain insight into the details of the mechanism, a series of control experiments were carried out. Firstly, the reaction of glycine derivative 1b and dioxene 4, as well as the reaction of imine 5 and dioxane 2 were investigated [Scheme 2, Eqs. (1) and (2)], the results indicate that dioxene and imine can be involved as intermediates in this CBr4-mediated tandem process. When HBr was used in the reaction of imine 5 and dioxene 4, the desired product 3q was obtained in a moderate yield [Scheme 2, Eq. (3)]. This result indicates that the in situ generated HBr is important for the subsequent [4+ +2] cycloaddition and ring opening Adv. Synth. Catal. 2016, 358, 724 – 730

Scheme 2. Control experiments.

process. No desired product was observed on addition of 1 equiv. of TEMPO as a radial scavenger in the reaction of 1b with 2 [Scheme 2, Eq. (4)]. This result suggests that the reaction includes a radical process. The reaction of 1b and 2 under an argon atmosphere was also investigated [Scheme 2, Eq. (5)], no desired product 3b was achieved. This result indicates that oxygen is crucial for the reaction. The visible lightmediated reaction of 1b and 2 using CCl3Br as promoter also delivered the desired product 3b in 32% yield. This result gave important evidence for the bromine radical-induced mechanism.[12] Finally, we also observed that, after the reaction, Ph3P=O could be isolated quantitatively. Although the mechanism of this transformation is not fully clarified yet, a plausible mechanism based

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Scheme 3. Proposed reaction mechanism.

on the experimental data described above is proposed in Scheme 3. CBr4 is initially attacked by very nucleophilic PPh3 to form phosphonium intermediate A as it happens in the Appel reaction. Then, a homolytic cleavage of the weak P¢Br bond occurs to form the PPh3 radical cation and a bromine radical. (The reaction of PPh3 radical cation with O2 and following SET affords Ph3P=O.)[13] Once the bromine radical is delivered, it can abstract the hydrogen atom from 1 or 2 to generate radical intermediate A or E, A or E then reacts with O2 to provide the peroxide radical B or F, which then abstracts a hydrogen atom from substrate 1 or 2 to form the hydroperoxide C or G and radical A or E. Elimination of the hydrogen peroxide, followed by a Povarov reaction, would furnish the [4+ +2] adduct I. Intermediate I is not stable under acidic conditions and generates the 2,3-disubstituted dihydroquinoline intermediate J through an acidic ring opening rearrangement process. Subsequently, aromatization of intermediate J occurred to afford the desired product 3. In summary, we have demonstrated a novel CBr4mediated, double-oxidative dehydrogenative (DOD) cyclization/acidic ring opening/aromatization tandem reaction of glycine derivatives with dioxane, leading 728

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to complex quinoline derivatives. This protocol preliminarily realizes our double-oxidative dehydrogenative (DOD) cyclization idea. The use of very inexpensive substrates (glycine derivatives and dioxane) and an extremely simple metal-free promoter (CBr4) with green molecular oxygen (air) as an oxidant make this protocol very attractive for potential synthetic applications. This work also proved again that CBr4 can be an efficient reagent to initiate radical reactions under mild reaction conditions. Further applications of these CBr4-mediated methodologies are ongoing in this laboratory.

Experimental Section General Procedure for CBr4-Promoted Aerobic Double-Oxidative Dehydrogenative (DOD) Cyclization Reaction of Glycine Esters with Dioxane Glycine derivatives (1, 1 mmol), CBr4 (0.15 mmol) and PPh3 (0.15 mmol) were dissolved in dioxane (50 mmol) at ambient temperature. The reactions were performed under an air atmosphere (open flask) at 80 8C and completed within 11– 17 hours as monitored by TLC. The products were isolated by column chromatographic separation.

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Double-Oxidative Dehydrogenative (DOD) Cyclization of Glycine Derivatives

Acknowledgements We thank the National Natural Science Foundation of China (21262029, 21562037) and the Fok Ying Tong Education Foundation (141116) for financially supporting this work.

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