Département de chimie moléculaire

Pyrido[4,3,2-kl]acridines, e.g., I, represent a new class of heterocycles, isomers of marine alkaloids. I reacts as an electron rich heterocycle, and in particular via regioselective electrophilic substitution such as H/D exchange and the Vilsmeier-Haack reaction to give the corresponding 6-substituted derivs. Pyrido[4,3,2-kl]acridin-4-one II reacts with amines and thiol, via 1,4-Michael addn. to give the 6-amino or 6-thio analogs in a very efficient way. Mol. calcns. account for the obsd. regioselectivity. [on SciFinder(R)]