Synthesis of 5‐Trifluoromethyl‐1,2,4‐Triazoles via Metal‐Free Annulation of Trifluoroacetimidohydrazides and Methyl Ketones | Zendy

Zhang Jiajun | Zendy; Tang Jianhua | Zendy; Chen Zhengkai | Zendy; Wu XiaoFeng | Zendy

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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.

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