Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3+2]-Cycloaddition of Nitrile Imines with CF3CN

被引：11
|
作者：
Lin, Bo [1 ]
Zhang, Zipeng [1 ]
Yao, Yunfei [1 ]
You, Yi [1 ]
Weng, Zhiqiang [1 ,2 ]
机构：
[1] Fuzhou Univ, Coll Chem, Fujian Prov Key Lab Electrochem Energy Storage Ma, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China
[2] Minjiang Univ, Coll Mat & Chem Engn, Fujian Engn Res Ctr New Chinese Lacquer Mat, Fuzhou 350108, Peoples R China
来源：
MOLECULES | 2022年 / 27卷 / 19期
基金：
中国国家自然科学基金;
关键词：
trifluoromethyl; triazole; cycloaddition; nitrile imines; trifluoroacetonitrile; 3+2 CYCLOADDITION; 2,5-BIS(TRIFLUOROMETHYL)-1,3,4-OXADIAZOLE; HYDRAZINE; FLUORINE;
D O I：
10.3390/molecules27196568
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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.
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页数：10
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