The Heck reaction of beta-arylacrylamides: An approach to 4-aryl-2-quinolones

The Heck reaction of beta-arylacrylamides with aryl iodides afforded the corresponding vinylic substitution products usually in high yields. The nature of beta-substituents, aryl iodides and substituents at the nitrogen atom influences the stereochemical outcome. N,N-Dimethyl-beta-arylacrylamides gave vinylic substitution products with higher stereoselectivity than the corresponding N-unsubstituted beta-arylacrylamides. beta-Arylacrylamides containing ortho-substituents led to the formation of only one stereoisomer. The procedure was used to prepare 4-aryl-2-quinol ones from beta-(o-bromophenyl)acrylamide through a sequential Heck reaction and copper-catalyzed cyclization process.