Three-Component Synthesis of 2-Alkylthiobenzoazoles in Aqueous Media

Jin-Quan Chen; Jia Guo; Zhi-Bing Dong

doi:10.1055/s-0039-1690854

Synthesis, Table of Contents

Synthesis 2020; 52(13): 1927-1933
DOI: 10.1055/s-0039-1690854

paper

Three-Component Synthesis of 2-Alkylthiobenzoazoles in Aqueous Media

Jin-Quan Chen

^aSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China Email: dzb04982@wit.edu.cn

,

Jia Guo

^bKey Laboratory of Green Chemical Process, Ministry of Education, Wuhan Institute of Technology, Wuhan 430205, P. R. of China

^cHubei Key Laboratory of Novel Reactor and Green Chemistry Technology, Wuhan Institute of Technology, Wuhan 430205, P. R. of China

,

Zhi-Bing Dong ∗

^aSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China Email: dzb04982@wit.edu.cn

^bKey Laboratory of Green Chemical Process, Ministry of Education, Wuhan Institute of Technology, Wuhan 430205, P. R. of China

^cHubei Key Laboratory of Novel Reactor and Green Chemistry Technology, Wuhan Institute of Technology, Wuhan 430205, P. R. of China

^dMinistry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University, Wuhan 430062, P. R. of China

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Abstract

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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.

Key words

metal-free - synthesis - thiobenzoazole - water - thiuram

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References

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20 CCDC 1971891 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

Supplementary Material