From Acyliminiums/Amidoallenyliums to Highly Functionalized Allene Intermediates: Stereoselective Preparation of <i>Z</i>‐Amidovinyl‐Furans, ‐Pyrroles, ‐Thiophenes, ‐Benzofurans and ‐Benzothiophenes

Abstract

Abstract This paper describes the development of a facile protocol to a highly functionalized amidoallenylium by treatment of alkynylimine with acyl bromide in dichloromethane, which may give tetrasubstituted allene intermediates and yield furans, pyrroles, thiophenes, benzofurans and benzothiophenes. The plausible mechanism was discussed and a reaction intermediate was isolated. With the stereoselective transformation of the tetrasubstituted allene intermediate and efficient conversion to versatile heterocyclic compounds, this protocol will be useful to the organic and medicinal chemistry community. magnified image