Matilde Sisti, Luca Sancineto, Francesca Marini, Claudio Santi, Luana Bagnoli* University of Perugia, Via del Liceo, 1 – 06123 Perugia e-mail:
[email protected]
Pyrazino-indole scaffold: attractive for biological activities
SELENONES
R
O + N H
KOH (2.5 equiv)
C6H13
1
NHR
1 a-b 1a: R = H; R1 = CH2Ph 1b: R = OMe; R1 = CH2Ph
SeO2Ph
2b
CH2Cl2 0°C to r.t. t = 48 h
R
O N C6H13 4 a-b 4a Yield 68% 4b Yield 50%
NR1
O
O
KOH
R
Michael addition
R N H
NHR
N
NHR
C6H13 SeO2Ph
O R N
O
proton transfer R
NHR
N
SeO2Ph
SN2 NR
SeO2Ph
C6H13
C6H13
O
R N
NR
C6H13 4-hexyl-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one
