A general and practicable synthesis of polycyclic heteroaromatic compounds. Part 2. Reaction of quinone-methides of pyridones, pyrimidines, coumarin, and benzene with aromatic amines in a novel synthesis of polycyclic heteroaromatic compounds

Abstract

The synthesis of polycyclic heteroaromatic compounds using the reaction of a quinone-methide, generated in situ, with an aromatic amine has been successfully extended using quinone-methides of coumarin and of pyridones. Preliminary studies with the benzenoid quinone-methide (33) have so far proved to give only low yields of the expected acridines. Generation of ‘quinone-methides’ in which the carbonyl is part of an amide group did not lead to polycyclic heteroaromatic compounds.