Synthesis of 2-trifluoromethyl thiazoles via [3 + 2] cycloaddition of pyridinium 1,4-zwitterionic thiolates with CF3CN

Yunfei Yao; Bo Lin; Minze Wu; Yafang Zhang; Yangjie Huang; Xiaoyan Han; Zhiqiang Weng

doi:10.1039/D2OB01749K

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Synthesis of 2-trifluoromethyl thiazoles via [3 + 2] cycloaddition of pyridinium 1,4-zwitterionic thiolates with CF₃CN†

Yunfei Yao,‡^ab Bo Lin,‡^b Minze Wu,^a Yafang Zhang,^a Yangjie Huang,*^a Xiaoyan Han*^c and Zhiqiang Weng

*^ab

Author affiliations

* Corresponding authors

^a Fujian Engineering Research Center of New Chinese lacquer Material, College of Materials and Chemical Engineering, Minjiang University, Fuzhou, China
E-mail: zweng@mju.edu.cn

^b Fujian Provincial Key Laboratory of Electrochemical Energy Storage Materials, College of Chemistry, Fuzhou University, Fuzhou, China

^c Testing and Analysis Center, Soochow University, Suzhou 215123, China

Abstract

2,2,2-Trifluoroacetaldehyde O-(aryl)oxime was employed for the [3 + 2] cycloaddition of pyridinium 1,4-zwitterionic thiolates for the synthesis of 2-trifluoromethyl 4,5-disubstituted thiazoles. The reaction works well with various substituted pyridinium 1,4-zwitterionic thiolates in moderate to good yields. The synthetic potential of the obtained 2-trifluoromethyl 4,5-disubstituted thiazoles was demonstrated.

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Article information

DOI: https://doi.org/10.1039/D2OB01749K
Article type: Paper
Submitted: 25 Sep 2022
Accepted: 13 Oct 2022
First published: 15 Oct 2022

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Org. Biomol. Chem., 2022,20, 8761-8765

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Synthesis of 2-trifluoromethyl thiazoles via [3 + 2] cycloaddition of pyridinium 1,4-zwitterionic thiolates with CF₃CN

Y. Yao, B. Lin, M. Wu, Y. Zhang, Y. Huang, X. Han and Z. Weng, Org. Biomol. Chem., 2022, 20, 8761 DOI: 10.1039/D2OB01749K

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Organic & Biomolecular Chemistry