Double C–S bond formation via multiple Csp3–H bond cleavage: synthesis of 4-hydroxythiazoles from amides and elemental sulfur under metal-free conditions

Liang Chen; Xinyu Xuchen; Fei Wang; Yuan Yang; Guobo Deng; Yilin Liu; Yun Liang

doi:10.1039/D1OB01989A

Double C–S bond formation via multiple Csp³–H bond cleavage: synthesis of 4-hydroxythiazoles from amides and elemental sulfur under metal-free conditions†

Liang Chen,^ac Xinyu Xuchen,^a Fei Wang,^a Yuan Yang,

^a Guobo Deng,

*^ad Yilin Liu

*^b and Yun Liang

*^a

Author affiliations

* Corresponding authors

^a National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha, Hunan 410081, China
E-mail: gbdeng@hunnu.edu.cn, yliang@hunnu.edu.cn

^b Institute of Organic Synthesis, College of Chemistry and Materials Engineering, Huaihua University, Huaihua 418008, China
E-mail: liuyilinhn@126.com

^c Huaihua Normal College, Huaihua 418008, China

^d Ministry of Education Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China

Abstract

A novel and efficient approach for the synthesis of 4-hydroxythiazoles from amides and elemental sulfur has been developed. In the presence of P₂O₅, DMSO and HMPA, this metal-free protocol proceeds smoothly and tolerates a spectrum of functional groups. Furthermore, this strategy involves the process of double Csp³–S bond formation through the cleavage of multiple Csp³–H bonds for the first time.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D1OB01989A
Article type: Communication
Submitted: 11 Oct 2021
Accepted: 03 Nov 2021
First published: 08 Nov 2021

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Org. Biomol. Chem., 2021,19, 10068-10072

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Double C–S bond formation via multiple Csp³–H bond cleavage: synthesis of 4-hydroxythiazoles from amides and elemental sulfur under metal-free conditions

L. Chen, X. Xuchen, F. Wang, Y. Yang, G. Deng, Y. Liu and Y. Liang, Org. Biomol. Chem., 2021, 19, 10068 DOI: 10.1039/D1OB01989A

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Organic & Biomolecular Chemistry