Au(III)-Catalyzed Tandem Amination-Hydration of Alkynes: Synthesis of α-(N-2-Pyridonyl)ketones

A new Au(III)-catalyzed tandem amination-hydration reaction has been discovered, leading to the formation of alpha-(N-2-pyridonyl)ketones and heterocyclic analogues in good to excellent yields (14 examples, 48-90%). This reaction demonstrates the unusual use of a heterocyclic sp(2) nitrogen nucleophile in a gold-catalyzed 6-endo-dig cyclization. The tandem process allows rapid access to alpha-(N-2-pyridonyl)ketones, making them a convenient building block for the synthesis of more complex N-alkyl pyridone targets.