A Convenient FeCl3‐Mediated Synthesis of 5‐Trifluoromethyl‐1,2,4‐triazoles from Trifluoroacetimidoyl Chlorides and Hydrazides

A low cost FeCl3‐mediated cascade annulation of trifluoroacetimidoyl chlorides and hydrazides for the efficient synthesis of 5‐trifluoromethyl‐1,2,4‐triazoles has been developed. The transformation proceeds through a cascade base‐promoted intermolecular C−N bond formation and FeCl3‐mediated intramol...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-11, Vol.362 (22), p.5130-5134
Main Authors: Du, Shiying, Wang, Le‐Cheng, Yang, Zuguang, Chen, Zhengkai, Wu, Xiao‐Feng
Format: Article
Language:English
Subjects:
5-trifluoromethyl-1,2,4-triazoles
cascade annulation reaction
Chemical reactions
Dehydration
Ferric chloride
Hydrazides
Iron chlorides
N-heterocyclic compounds
Synthesis
Triazoles
trifluoroacetimidoyl chlorides
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Summary:A low cost FeCl3‐mediated cascade annulation of trifluoroacetimidoyl chlorides and hydrazides for the efficient synthesis of 5‐trifluoromethyl‐1,2,4‐triazoles has been developed. The transformation proceeds through a cascade base‐promoted intermolecular C−N bond formation and FeCl3‐mediated intramolecular dehydration sequence under mild conditions. The protocol exhibits many notable features and can be readily scaled up to gram scale.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202001015