Dearomative Ring-Opening of N-Fused Heteroarenes: Access to Tetrasubstituted Alkenes and Ketimines

Abstract

We report a novel and efficient strategy for constructing tetrasubstituted alkenes and α-iminonitriles from 3-aminoindolizines and 3-aminoimidazo[1,2-a]pyridines. This approach involves a dearomative ring-opening of N-fused heteroaromatic amines coupled to a DDQ-mediated oxidative process under mild, metal-free conditions. The methodology demonstrates broad substrate scope, excellent functional group tolerance, and scalability, offering a versatile platform for synthesizing complex alkenes and nitrile-containing frameworks.