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Synthesis 2020; 52(13): 1927-1933
DOI: 10.1055/s-0039-1690854
DOI: 10.1055/s-0039-1690854
paper
Three-Component Synthesis of 2-Alkylthiobenzoazoles in Aqueous Media
The financial support from Hubei Key Laboratory of Radiation Chemistry and Functional Materials, Hubei University of Science & Technology (2019-20KZ01), Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University (KLSAOFM1810), Science and Technology Department of Hubei Province (2019CFB596), Key Laboratory of Hubei Province for Coal Conversion and New Carbon Materials (WKDM202003) are all greatly appreciated. J.-Q.C. thanks the support of Postgraduate Innovation Foundation from Wuhan Institute of Technology (CX2019170).Further Information
Publication History
Received: 19 December 2019
Accepted after revision: 14 February 2020
Publication Date:
16 March 2020 (online)
Abstract
A highly efficient three-component protocol for the synthesis of the 2-alkylthiobenzoazoles is described. Tetramethylthiuram disulfide (TMTD) cyclized with o-aminothiophenols, generating the intermediate 2-mercaptobenzothiazoles, and the successive C–S coupling with halogenated alkanes afforded a series of 2-alkyl-substituted thiobenzothiazoles smoothly in a one-pot process. This procedure could also be utilized for the preparation of 2-alkyl-substituted thiobenzoxazoles and 2-alkyl-substituted thiobenzimidazoles. Inexpensive and easily available starting materials, metal catalyst-free, broad substrate scope, and water as solvent are the features of this protocol.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690854.
- Supporting Information
- CIF File
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