Oxidative Cascade Reaction of N-Aryl-3-alkylideneazetidines and Carboxylic Acids: Access to Fused Pyridines.

Abstract

A versatile silver-promoted oxidative cascade reaction of N-aryl-3-alkylideneazetidines with carboxylic acids is reported, providing a very efficient pathway to functionalized fused pyridines. This method allows introduction of fused pyridine ring systems to heterocycles, drugs, and natural products. A mechanistic study revealed that silver salt is essential for the chemo- and regioselective ring expansion, sequential oxidative nucleophilic additions, and oxidative aromatization. This approach represents the first example of the strained N-heterocycles undergoing a cascade reaction with a π bond and a nucleophile together.