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

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...

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Bibliographic Details
Published in:Organic letters 2021-04, Vol.23 (8), p.3076-3082
Main Authors: Zhang, Biao, Liu, Donghan, Sun, Yulin, Zhang, Yajing, Feng, Jiayi, Yu, Fuchao
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00751