One-flask synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from nitriles and hydrazonoyl chlorides via 1,3-dipolar cycloaddition

被引：26

作者：

Wang, Li-Ya ^{[1
,2
]}

Tsai, Henry J. ^{[3
]}

Lin, Hui-Yi ^{[4
]}

Kaneko, Kimiyoshi ^{[5
]}

Cheng, Fen-Ying ^{[6
]}

Shih, Hsin-Siao ^{[6
]}

Wong, Fung Fuh ^{[1
]}

Huang, Jiann-Jyh ^{[6
]}

机构：

[1] China Med Univ, Grad Inst Pharmaceut Chem, Taichung 40402, Taiwan

[2] China Med Univ, PhD Program Canc Biol & Drug Discovery, Taichung 40402, Taiwan

[3] Asia Univ, Dept Hlth & Nutr Biotechnol, Taichung 41354, Taiwan

[4] China Med Univ, Sch Pharm, Taichung 40402, Taiwan

[5] Nihon Pharmaceut Univ, Dept Med Pharmaceut Sci, Saitama 10281, Japan

[6] Natl Chiayi Univ, Dept Appl Chem, Chiayi 60004, Taiwan

来源：

RSC ADVANCES | 2014年 / 4卷 / 27期

关键词：

MICROWAVE-ASSISTED SYNTHESIS; 3,5-DISUBSTITUTED 1,2,4-TRIAZOLES; REGIOSELECTIVE SYNTHESIS; NITRILIMINE CYCLOADDITION; BIOLOGICAL EVALUATION; DERIVATIVES; DISCOVERY; INHIBITORS;

D O I：

10.1039/c4ra00113c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A one-flask strategy for the synthesis of 1,3,5-trisubstituted 1,2,4-triazoles 4a-s and 8a and b from nitriles 5a-i with N-arylhydrazonoyl hydrochlorides 3a-h and 7a and b under basic conditions was developed. The reaction provided the desired 1,2,4-triazoles in moderate to excellent yields (56-98%), and was applicable to aliphatic and aromatic nitriles as well as N-phenylhydrazonoyl hydrochlorides bearing ester and acetyl functionalities. A 1,3-dipolar cycloaddition between imidate and nitrilimine generated from the respective nitrile and N-arylhydrazonoyl chloride in one flask was proposed for the new transformation.

引用

页码：14215 / 14220

页数：6

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