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

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

Org Biomol Chem. 2022 Nov 16;20(44):8761-8765. doi: 10.1039/d2ob01749k.

Authors

Yunfei Yao^{1

2}, Bo Lin², Minze Wu¹, Yafang Zhang¹, Yangjie Huang¹, Xiaoyan Han³, Zhiqiang Weng^{1

2}

Affiliations

¹ Fujian Engineering Research Center of New Chinese lacquer Material, College of Materials and Chemical Engineering, Minjiang University, Fuzhou, 350108, China. zweng@mju.edu.cn.
² Fujian Provincial Key Laboratory of Electrochemical Energy Storage Materials, College of Chemistry, Fuzhou University, Fuzhou, 350108, China.
³ Testing and Analysis Center, Soochow University, Suzhou 215123, China.

PMID: 36314533
DOI: 10.1039/d2ob01749k

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cycloaddition Reaction
Thiazoles*

Substances

Thiazoles