Issue 13, 2022

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
03 May 2022
Accepted
08 Jun 2022
First published
09 Jun 2022

Green Chem., 2022,24, 5058-5063

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

H. Guo, Y. Liu, C. Wen and J. Wan, Green Chem., 2022, 24, 5058 DOI: 10.1039/D2GC01644C

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