Gold(i)-catalyzed synthesis of N-alkenyl 2-pyridonyl sec-amines

Abstract

N-Alkenyl 2-pyridonyl amines are afforded in high yields via a gold-catalyzed rearrangement of 2-propargyloxypyridine and 2-(but-3-yn-1-yloxy)pyridine under acidic conditions. This approach exhibits significant utility due to its outstanding efficiency of conversion in the synthesis of secondary amines as a one-pot reaction. The initial step of the method involves a cyclization reaction for the production of pyridinium salts, followed by the next stage, where rearrangement is accomplished through the nucleophilic addition phenomenon. This approach provides the conversion of primary amines into secondary amines, resulting in a single product. Furthermore, the methodology presents a high degree of tolerance towards several pyridine and aniline derivatives, resulting in the formation of products with excellent yields.