Author:
Lin Bo,Zhang Zipeng,Yao Yunfei,You Yi,Weng Zhiqiang
Abstract
We herein describe a general approach to 5-trifluoromethyl 1,2,4-triazoles via the [3 + 2]-cycloaddition of nitrile imines generated in situ from hydrazonyl chloride with CF3CN, utilizing 2,2,2-trifluoroacetaldehyde O-(aryl)oxime as the precursor of trifluoroacetonitrile. Various functional groups, including alkyl-substituted hydrazonyl chloride, were tolerated during cycloaddition. Furthermore, the gram-scale synthesis and common downstream transformations proved the potential synthetic relevance of this developed methodology.
Funder
National Natural Science Foundation of China
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Cited by
6 articles.
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1. Fluorine‐Containing Functional Group‐Based Energetic Materials;The Chemical Record;2023-06-02
2. Synthesis of 1,2,4‐Triazoles and 1,3,4‐Thiadiazinones by [3+2] and [3+3] Domino Annulation Reactions of Nitrile Imines with Succinimide and Thiazolidine‐2,4‐dione;Asian Journal of Organic Chemistry;2023-03-20
3. Facile Synthesis of Fully Substituted 1,2,4‐Triazoles via [3+2] Cycloaddition of Nitrileimines with Amidine under Transition Metal‐Free Conditions;Asian Journal of Organic Chemistry;2023-01
4. Recent developments in the chemistry of 1H- and 4H-1,2,4-triazoles;Advances in Heterocyclic Chemistry;2023
5. Synthesis of 3-substituted 2-trifluomethyl imidazo[1,2-a]pyridine through [3+2] cycloaddition of pyridinium ylide with trifluoroacetonitrile;Tetrahedron Letters;2022-11