Synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro-2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium-5-aminides

被引：11

作者：

Araki, Shuki ^{[1
]}

Hirose, Satoshi ^{[1
]}

Konishi, Yoshikazu ^{[1
]}

Nogura, Masatoshi ^{[1
]}

Hirashita, Tsunehisa ^{[1
]}

机构：

[1] Nagoya Inst Technol, Omohi Coll, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 5卷

关键词：

formazan; mesoionic compounds; nucleophilic substitution; tetrazolium; 1,2,4-triazole;

D O I：

10.3762/bjoc.5.8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of a 5-chloro-2,3-diphenyltetrazolium salt with amines have been examined. In the presence of an inorganic base such as NaHCO(3), primary and secondary amines undergo a nucleophilic substitution to give the corresponding 5-aminotetrazolium salts. When triethylamine is used as a base, primary amines give 3-phenylazo-1,2,4-triazoles. A plausible dual-path mechanism is proposed for the formation of the triazoles via Type B mesoionic tetrazolium-5-aminides.

引用

页数：6