A New Synthesis Strategy for Rhodanine and Its Derivatives

Abstract

Rhodanine and its derivatives have been known as privileged structures in pharmacological research because of their wide spectrum of biological activities, but the synthesis method of rhodanine skeleton is limited. In this paper, not only rhodanine skeleton, but also N-aryl rhodanines can be directly prepared via the reaction of thioureas and thioglycolic acid in one step catalyzed by protic acid, which provides a new approach of the synthesis of rhodanine and its derivatives. The developed strategy is straightforward, efficient, atom economical and convenient in good yields.

Base-Promoted Formal [3 + 2] Cycloaddition of α-Halohydroxamates with Carbon Disulfide to Synthesize Polysubstituted Rhodanines

“…Given their significant values in drug discovery and organic chemistry, rhodanine and related scaffolds have attracted the considerable attention of the synthetic chemists, and some efficient synthetic methods have been developed in the past several years . Favi and co-workers reported an elegant [1 + 2 + 2 ] cycloaddition for the synthesis of functionalized 5-hydrazinoalkylidene rhodanine derivatives by the three-component reaction of aliphatic primary amines, carbon disulfides, and 1,2-diaza-1,3-dienes (Scheme a) .…”