Palladium-Catalyzed anti-Michael-Type Hydroamination of N-(Quinolin-8-yl)acrylamide with 2-Pyridones

Abstract

Here we report a palladium-catalyzed anti-Michaeltype hydroamination of N-(quinolin-8-yl)acrylamide with 2pyridones. The use of a palladium catalyst enables the α-addition of 2-pyridones, resulting in the formation of a range of N-substituted 2-pyridone carboxamides with yields ranging from 10% to 80%. Derivatization of the products highlights the utility of this transformation. Preliminary mechanistic investigations suggest that the reaction proceeds through the direct addition of a nitrogen atom of 2-pyridones, ruling out other pathways such as O-to-N-alkyl migration.N-Alkylated 2-pyridones are a prevalent structural motif in a wide array of naturally occurring and biologically active compounds (Scheme 1A). 1−3 Consequently, numerous