Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions

[Image: see text] A general approach for preparation of two types of polyfunctionalized 3-trifluoromethylpyrazoles is reported. The protocol comprises (3 + 2)-cycloaddition of the in situ generated trifluoroacetonitrile imines with enones leading to trans-configured 5-acyl-pyrazolines in a fully reg...

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Autores principales: Kowalczyk, Anna, Utecht-Jarzyńska, Greta, Mlostoń, Grzegorz, Jasiński, Marcin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9003577/
https://www.ncbi.nlm.nih.gov/pubmed/35343703
http://dx.doi.org/10.1021/acs.orglett.2c00521
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author Kowalczyk, Anna
Utecht-Jarzyńska, Greta
Mlostoń, Grzegorz
Jasiński, Marcin
author_facet Kowalczyk, Anna
Utecht-Jarzyńska, Greta
Mlostoń, Grzegorz
Jasiński, Marcin
author_sort Kowalczyk, Anna
collection PubMed
description [Image: see text] A general approach for preparation of two types of polyfunctionalized 3-trifluoromethylpyrazoles is reported. The protocol comprises (3 + 2)-cycloaddition of the in situ generated trifluoroacetonitrile imines with enones leading to trans-configured 5-acyl-pyrazolines in a fully regio- and diastereoselective manner. Initially formed cycloadducts were aromatized by treatment with manganese dioxide. Depending on the solvent used, the oxidation step either led to fully substituted pyrazoles (DMSO) or proceeded via a deacylative pathway to afford 1,3,4-trisubstituted derivatives (hexane) with excellent selectivity.
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spelling pubmed-90035772022-04-13 Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions Kowalczyk, Anna Utecht-Jarzyńska, Greta Mlostoń, Grzegorz Jasiński, Marcin Org Lett [Image: see text] A general approach for preparation of two types of polyfunctionalized 3-trifluoromethylpyrazoles is reported. The protocol comprises (3 + 2)-cycloaddition of the in situ generated trifluoroacetonitrile imines with enones leading to trans-configured 5-acyl-pyrazolines in a fully regio- and diastereoselective manner. Initially formed cycloadducts were aromatized by treatment with manganese dioxide. Depending on the solvent used, the oxidation step either led to fully substituted pyrazoles (DMSO) or proceeded via a deacylative pathway to afford 1,3,4-trisubstituted derivatives (hexane) with excellent selectivity. American Chemical Society 2022-03-28 2022-04-08 /pmc/articles/PMC9003577/ /pubmed/35343703 http://dx.doi.org/10.1021/acs.orglett.2c00521 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Kowalczyk, Anna
Utecht-Jarzyńska, Greta
Mlostoń, Grzegorz
Jasiński, Marcin
Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions
title Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions
title_full Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions
title_fullStr Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions
title_full_unstemmed Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions
title_short Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions
title_sort trifluoromethylated pyrazoles via sequential (3 + 2)-cycloaddition of fluorinated nitrile imines with chalcones and solvent-dependent deacylative oxidation reactions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9003577/
https://www.ncbi.nlm.nih.gov/pubmed/35343703
http://dx.doi.org/10.1021/acs.orglett.2c00521
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