Enhancing the potential of the Michael addition reaction using Betti base-thiourea-derived organocatalysts for the one-pot synthesis of 2,4-disubstituted pyrroles

Abstract

A novel class of Betti base-thiourea-derived bifunctional organocatalysts have been synthesized. The hydroxy group of the naphthyl ring (Betti base) and substituted thiourea moiety effectively enhances the reactivity through hydrogen bonding and facilitates the Michael addition reaction of methyl ketones to nitroolefins, affording 2,4-disubstituted pyrroles, which are core structural motifs in pharmaceuticals and optoelectronic and agrochemicals materials. The comprehensive reaction optimization and broad substrate scope evaluation with moderate to high yields (75–93%) highlight the versatility and efficiency of this catalytic system under mild reaction conditions.