Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF(3)CN

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 CF(3)CN, utilizing 2,2,2-trifluoroacetaldehyde O-(aryl)oxime as the precursor of trifluoroacetonitrile. Various functional groups...

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Detalles Bibliográficos
Autores principales: Lin, Bo, Zhang, Zipeng, Yao, Yunfei, You, Yi, Weng, Zhiqiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9572902/
https://www.ncbi.nlm.nih.gov/pubmed/36235104
http://dx.doi.org/10.3390/molecules27196568
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author Lin, Bo
Zhang, Zipeng
Yao, Yunfei
You, Yi
Weng, Zhiqiang
author_facet Lin, Bo
Zhang, Zipeng
Yao, Yunfei
You, Yi
Weng, Zhiqiang
author_sort Lin, Bo
collection PubMed
description 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 CF(3)CN, 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.
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spelling pubmed-95729022022-10-17 Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF(3)CN Lin, Bo Zhang, Zipeng Yao, Yunfei You, Yi Weng, Zhiqiang Molecules Article 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 CF(3)CN, 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. MDPI 2022-10-04 /pmc/articles/PMC9572902/ /pubmed/36235104 http://dx.doi.org/10.3390/molecules27196568 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Lin, Bo
Zhang, Zipeng
Yao, Yunfei
You, Yi
Weng, Zhiqiang
Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF(3)CN
title Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF(3)CN
title_full Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF(3)CN
title_fullStr Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF(3)CN
title_full_unstemmed Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF(3)CN
title_short Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF(3)CN
title_sort regioselective synthesis of 5-trifluoromethyl 1,2,4-triazoles via [3 + 2]-cycloaddition of nitrile imines with cf(3)cn
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9572902/
https://www.ncbi.nlm.nih.gov/pubmed/36235104
http://dx.doi.org/10.3390/molecules27196568
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