Electrochemical enaminone C–H thiolation/C–N amination cascade for thiazole synthesis and its diastereoselective dearomatization

Abstract

An electrochemical method for the synthesis of 2-aminothiazoles via aryl ring construction using enaminones and thioureas is reported. The cascade enamine C–H thiolation and C–N amination constitutes a major transformation for the thiazole ring formation. Moreover, a simple modification of electrochemical conditions enables the tunable dearomatization of the thiazole ring via vicinal dialkoxylation, leading to the synthesis of 4,5-dialkoxyl thiazolines bearing a quaternary carbon center with excellent diastereoselectivity.