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Preparation of Thiazole-2-thiones through TBPB-Promoted Oxidative Cascade Cyclization of Enaminones with Elemental Sulfur

Biao Zhang, Donghan Liu, Yulin Sun, Yajing Zhang, Jiayi Feng and Fuchao Yu*

*Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P. R. China, Email: yufckust.edu.cn

B. Zhan, D. Liu, Y. Sun, Y. Zhang, J. Feng, F. Yu, Org. Lett., 2021, 23, 3076-3082.

DOI: 10.1021/acs.orglett.1c00751 (free Supporting Information)


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Abstract

An oxidative cascade cyclization strategy enables an unprecedented construction of thiazole-2-thiones from enaminones via a cascade of C(sp2)-H/C(sp2)-H bond sulfurations and C(sp3)-H bond thiocarbonylation. This transformation allows for the efficient synthesis of thiazole-2-thiones with broad tolerance in moderate to excellent yields from simple enaminones with elemental sulfur.


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proposed mechanism



Key Words

N-heterocycles, S-heterocycles, TBPB


ID: J54-Y2021