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

[41] Synthesis and transformations of 3-aryl-5-dichloromethyl-1H-1,2,4-triazoles
P. A. Sokolyuk
B. A. Demidchuk
V. S. Brovarets
Russian Journal of General Chemistry, 2010, 80 : 1697 - 1702
[42] HETEROCYCLIC NITROCOMPOUNDS .5. 1-METHY-3-NITRO-5-ALKOXY-1,2,4-TRIAZOLES AND 1-METHY-3-NITRO-5-PHENOXY-1,2,4-TRIAZOLES
BAGAL, LI
PEVZNER, MS
SAMARENK.VY
EGOROV, AP
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1970, (05): : 702 - &
[43] Synthesis and transformations of 3-aryl-5-dichloromethyl-1H-1,2,4-triazoles
Sokolyuk, P. A.
Demidchuk, B. A.
Brovarets, V. S.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2010, 80 (08) : 1697 - 1702
[44] SYNTHESIS OF 1-PHENYL-3-(VINYLTHIO)-1,2,4-TRIAZOLES AND 5-PHENYL-3-(VINYLTHIO)-1,2,4-TRIAZOLES AND THEIR PROTON NMR-SPECTRA TRANSFORMED BY COMPLEXATION
TRZHTSINSKAYA, BV
RUDAKOVA, EV
AFONIN, AV
VORONOV, VK
PERTSIKOV, BZ
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1986, 35 (12): : 2516 - 2518
[45] Synthesis of 2-trifluoromethyl benzimidazoles, benzoxazoles, and benzothiazoles via condensation of diamines or amino(thio)phenols with CF3CN
Lin, Bo
Yao, Yunfei
Wu, Minze
Qin, Lu
Chen, Shouxiong
You, Yi
Weng, Zhiqiang
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (23) : 4788 - 4793
[46] Expanding the chemical space of 3(5)-functionalized 1,2,4-triazoles
Dmytro M. Khomenko
Roman O. Doroshchuk
Yulia M. Ohorodnik
Hanna V. Ivanova
Borys V. Zakharchenko
Ilona V. Raspertova
Oleksandr V. Vaschenko
Alexey V. Dobrydnev
Oleksandr O. Grygorenko
Rostyslav D. Lampeka
Chemistry of Heterocyclic Compounds, 2022, 58 : 116 - 128
[47] Novel Method for the synthesis of 1,2,4-triazoles and 1,2,4-triazol-3-ones
Chouaieb, H
Ben Mosbah, M
Kossentini, M
Salem, M
SYNTHETIC COMMUNICATIONS, 2003, 33 (22) : 3861 - 3868
[48] 1,2,4-TRIAZOLES .8. SYNTHESIS AND ANTI-MICROBIAL ACTIVITY OF 3-ALKYLTHIO-5-PYRIDYL-1,2,4-TRIAZOLES AND RELATED COMPOUNDS
KUBOTA, S
UDA, M
SATO, K
CHEMICAL & PHARMACEUTICAL BULLETIN, 1978, 26 (03) : 893 - 897
[49] SYNTHESIS OF (+/-)-SEPTICINE AND (+/-)-TYLOPHORINE BY REGIOSELECTIVE [3+2] CYCLOADDITION
IIDA, H
TANAKA, M
KIBAYASHI, C
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (06) : 271 - 272
[50] [3+2] Cycloaddition of Nitrile Imines with Enamides: An Approach to Functionalized Pyrazolines and Pyrazoles
Tu, Liang
Gao, Limei
Wang, Xiaomeng
Shi, Ruijie
Ma, Rupei
Li, Junfei
Lan, Xiaoshuang
Zheng, Yongsheng
Liu, Jikai
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 559 - 573

← 1 2 3 4 5 →