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Synthesis of 2‐Substituted 1,2,3‐Triazoles via an Intramolecular N – N Bond Formation
Author(s) -
Chen Chengyi,
Lu Xiaowei,
Holland Mareike C.,
Lv Shichang,
Ji Xuebao,
Liu Wei,
Liu Jie,
Depre Dominique,
Westerduin Pieter
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901519
Subject(s) - intramolecular force , chemistry , hydrazone , moiety , aryl , intramolecular reaction , stereochemistry , medicinal chemistry , organic chemistry , alkyl
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.