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

Here we report a palladium-catalyzed anti-Michael-type hydroamination of N-(quinolin-8-yl)acrylamide with 2-pyridones. 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.