A Method for Pyrrole Synthesis through Intramolecular Cyclization of γ-Alkynyl Oximes Promoted by SmI2

Abstract

AbstractA new strategy for the synthesis of pyrrole through intramolecular cyclization of γ-alkynyl oximes promoted by SmI2 is reported for the first time. In contrast to the prior methods, the selection of oxime instead of oxime ether or ester as substrate makes the synthetic method without accompaniment of organic waste (ArCO2H, AcOH, or ROH) because the hydroxyl group in oxime acts as the leaving group and is finally removed in the form of water molecule in the reaction. From a synthetic point of view, a series of pyrroles were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.