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Synthesis of 5‐Trifluoromethyl‐1,2,4‐Triazoles via Metal‐Free Annulation of Trifluoroacetimidohydrazides and Methyl Ketones
Author(s) -
Zhang Jiajun,
Tang Jianhua,
Chen Zhengkai,
Wu XiaoFeng
Publication year - 2021
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.202100130
Subject(s) - annulation , chemistry , trifluoromethyl , aromatization , intramolecular force , condensation , intermolecular force , combinatorial chemistry , halogenation , stereochemistry , medicinal chemistry , organic chemistry , molecule , catalysis , physics , thermodynamics , alkyl
A metal‐free approach for the synthesis of 5‐trifluoromethyl‐1,2,4‐triazoles via I 2 ‐mediated [4+1] annulation of readily available trifluoroacetimidohydrazides and methyl ketones has been achieved. The transformation involves iodination/Kornblum oxidation, intermolecular dehydration condensation and an iodine‐mediated intramolecular cyclization/aromatization sequence. The developed protocol can be easily scaled up to 3 mmol scale without obvious efficiency decrease and be implemented by a consecutive one‐pot manner.