Synthesis of 2-Substituted 1,2,3-Triazoles via an Intramolecular N-N Bond Formation

被引：13

作者：

Chen, Cheng-yi ^{[1
]}

Lu, Xiaowei ^{[2
]}

Holland, Mareike C. ^{[3
]}

Lv, Shichang ^{[2
]}

Ji, Xuebao ^{[2
]}

Liu, Wei ^{[2
]}

Liu, Jie ^{[2
]}

Depre, Dominique ^{[3
]}

Westerduin, Pieter ^{[3
]}

机构：

[1] Janssen R&D, API Small Mol Dev, Discovery Prod Dev & Supply, Hochstr 201, CH-8205 Schaffhausen, Switzerland

[2] Porton Shanghai R&D Ctr, Zizhu Sci Pk,1299 Ziyue Rd, Shanghai 200241, Peoples R China

[3] Janssen R&D, API Small Mol Dev, Discovery Prod Dev & Supply, Turnhoutseweg 30, B-2340 Beerse, Belgium

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 05期

关键词：

Intramolecular; N-N bond formation; 2-Aryl; 1; 2; 3-triazole; SN2; Displacement; Reaction mechanisms;

D O I：

10.1002/ejoc.201901519

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of 2-aryl 1,2,3-triazoles based on an intramolecular N-N bond formation is described. Selective activation of bis-hydrazone at the dimethylamino hydrazone group with MeI forms a mono-hydrazonium species. Treatment of the hydrazonium species with a base smoothly leads to the formation of a wide variety of 2-aryl-1,2,3-triazoles in good to excellent yields. The reaction likely follows an intramolecular S(N)2 displacement mechanism with the trimethylammonium moiety serving as a good leaving group for the intramolecular N-N bond formation.

引用

页码：548 / 551

页数：4

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