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.

引用

页数：10

共 50 条

[1] Regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles via photocycloaddition of sydnone with CF3CN
Lin, Bo
Yao, Yunfei
Huang, Yangjie
Lin, Qi
Weng, Zhiqiang
CHEMICAL COMMUNICATIONS, 2022, 58 (87) : 12224 - 12227
[2] Mechanochemical Synthesis of 1,2,4-Triazoles via a [3+2] Cycloaddition of Azinium-N-Imines and Nitriles
Zhu, Baofu
Li, Wen
Chen, Haixin
Wu, Minjian
Hu, Jijing
Cao, Hua
Liu, Xiang
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (17) : 2911 - 2915
[3] Synthesis of 2-trifluoromethyl thiazoles via [3+2] cycloaddition of pyridinium 1,4-zwitterionic thiolates with CF3CN
Yao, Yunfei
Lin, Bo
Wu, Minze
Zhang, Yafang
Huang, Yangjie
Han, Xiaoyan
Weng, Zhiqiang
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (44) : 8761 - 8765
[4] Synthesis of fused 3-trifluoromethyl-1,2,4-triazoles via base-promoted [3+2] cycloaddition of nitrile imines and 1H-benzo[d]imidazole-2-thiols
Cen, Kaili
Wei, Jiahao
Feng, Yuting
Liu, Yuan
Wang, Xinye
Liu, Yangyu
Yin, Yalin
Yu, Junhong
Wang, Dahan
Cai, Jinhui
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (35) : 7095 - 7099
[5] SYNTHESIS OF FUSED RING 1,2,4-TRIAZOLES BY INTRAMOLECULAR CYCLOADDITION OF NITRILE IMINES TO NITRILE FUNCTION
GARANTI, L
SCANDROGLIO, A
ZECCHI, G
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (06) : 1339 - 1341
[6] OXAZOLONES .6. REACTION OF 5(4H)-OXAZOLONES WITH NITRILE IMINES - SYNTHESIS OF 1H-1,2,4-TRIAZOLES THROUGH [3+2] CYCLOADDITION
GELMI, ML
POCAR, D
RIVA, R
HETEROCYCLES, 1992, 34 (02) : 315 - 320
[7] Synthesis of 1,2,4-Triazoles via the Electrochemical Oxidative [3+2] Annulation
Zhao, Zhiheng
Li, Ming
Zhou, Yaqin
He, Yonghui
Zhang, Lizhu
Li, Ganpeng
Gu, Lijun
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (06) : 2476 - 2484
[8] Regioselective synthesis of spiro naphthofuranone-pyrazoline via a [3+2] cycloaddition of benzoaurones with nitrile imines
Su, Yingpeng
Ma, Chenglong
Zhao, Yanan
Yang, Caixia
Feng, Yawei
Wang, Ke-Hu
Huang, Danfeng
Huo, Congde
Hu, Yulai
TETRAHEDRON, 2020, 76 (31-32)
[9] 1,2,4-TRIAZOLES .2. SYNTHESIS OF 1,5-DIPHENYL-3-TRIFLUOROMETHYL-1H-1,2,4-TRIAZOLES
CZOLLNER, L
SZILAGYI, G
LANGO, J
JANAKY, J
MONATSHEFTE FUR CHEMIE, 1988, 119 (03): : 349 - 353
[10] Copper-mediated [3+2] cycloaddition of trifluoroacetimidoyl chlorides and N-isocyanoiminotriphenylphosphorane for the synthesis of 3-trifluoromethyl-1,2,4-triazoles
Yang, Hefei
Lu, Shu-Ning
Song, Yufei
Chen, Zhengkai
Wu, Xiao-Feng
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (18): : 5040 - 5044

← 1 2 3 4 5 →