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; Fuchao Yu

doi:10.1021/acs.orglett.1c00751

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

Org Lett. 2021 Apr 16;23(8):3076-3082. doi: 10.1021/acs.orglett.1c00751. Epub 2021 Mar 26.

Authors

Biao Zhang¹, Donghan Liu¹, Yulin Sun¹, Yajing Zhang¹, Jiayi Feng¹, Fuchao Yu¹

Affiliation

¹ Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P. R. China.

PMID: 33769063
DOI: 10.1021/acs.orglett.1c00751

Abstract

An unprecedented method for the construction of thiazole-2-thiones via an oxidative cascade cyclization strategy is described. The novel protocol involves the simultaneous formation of two C-S bonds and a C═S bond on the structure of enaminones in a single operation through a cascade of C(sp²)-H/C(sp³)-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.