Direct catalyst-free synthesis of substituted imidazolidinone-rhodanine hybrids via functional group migration

Abstract

A green synthetic method has been developed for producing novel rhodanine-based hybrid derivatives. Initially, rapid synthesis of 5-alkoxycarbonylmethylidene-1,3-thiazolidine-4-one derivatives 1a-1d was achieved by reacting N,N-disubstituted thioureas with dialkyl acetylene dicarboxylates under catalyst-free conditions at room temperature, resulting in excellent yields (90–95%). Subsequently, the reaction between compounds 1a-1d and primary amines 2a-2e in the presence of carbon disulfide was carried out under similar catalyst-free conditions, yielding novel imidazolidinone-rhodanine hybrid derivatives 4a-4h with good to excellent yields (72–92%).

Graphical abstract