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TBAI or KI‐Promoted Oxidative Coupling of Enamines and N ‐Tosylhydrazine: An Unconventional Method toward 1,5‐ and 1,4,5‐Substituted 1,2,3‐Triazoles
Author(s) -
Huang Wei,
Zhu Chuanle,
Li Minke,
Yu Yue,
Wu Wanqing,
Tu Zhengchao,
Jiang Huanfeng
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800487
Subject(s) - chemistry , combinatorial chemistry , oxidation process , oxidative coupling of methane , medicinal chemistry , iodine , catalysis , organic chemistry , engineering , pulp and paper industry
A novel method for the synthesis of 1,5‐ and 1,4,5‐substituted 1,2,3‐triazoles has been reported. This approach is promoted by iodine‐TBHP oxidation system using enamines and N ‐tosylhydrazine as materials, which avoid the dependence of traditional methods on azides and transition metals. Through this approach, various 1,5‐ and 1,4,5‐substituted 1,2,3‐triazoles were delivered in moderate to high yields. The mechanistic study indicated that an amino exchange would be involved in the reaction process. Moreover, the product methyl 1‐(2‐methoxyphenyl)‐4‐methyl‐1 H ‐1,2,3‐triazole‐5‐carboxylate is a useful precursor to anti‐influenza A agent, and further application research was conducted.