Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF<sub>3</sub>CN
Bo Lin,
Zipeng Zhang,
Yunfei Yao,
Yi You,
Zhiqiang Weng
Affiliations
Bo Lin
Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Provincial Key Laboratory of Electrochemical Energy Storage Materials, College of Chemistry, Fuzhou University, Fuzhou 350108, China
Zipeng Zhang
Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Provincial Key Laboratory of Electrochemical Energy Storage Materials, College of Chemistry, Fuzhou University, Fuzhou 350108, China
Yunfei Yao
Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Provincial Key Laboratory of Electrochemical Energy Storage Materials, College of Chemistry, Fuzhou University, Fuzhou 350108, China
Yi You
Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Provincial Key Laboratory of Electrochemical Energy Storage Materials, College of Chemistry, Fuzhou University, Fuzhou 350108, China
Zhiqiang Weng
Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Provincial Key Laboratory of Electrochemical Energy Storage Materials, College of Chemistry, Fuzhou University, Fuzhou 350108, China
We herein describe a general approach to 5-trifluoromethyl 1,2,4-triazoles via the [3 + 2]-cycloaddition of nitrile imines generated in situ from hydrazonyl chloride with CF3CN, utilizing 2,2,2-trifluoroacetaldehyde O-(aryl)oxime as the precursor of trifluoroacetonitrile. Various functional groups, including alkyl-substituted hydrazonyl chloride, were tolerated during cycloaddition. Furthermore, the gram-scale synthesis and common downstream transformations proved the potential synthetic relevance of this developed methodology.
