Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes

The intramolecular oxidative cycloaddition reaction of alkyne- or alkene-tethered aldoximes was catalyzed efficiently by hypervalent iodine(III) species to afford the corresponding polycyclic isoxazole derivatives in up to a 94% yield. The structure of the prepared products was confirmed by various...

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Autores principales: Mironova, Irina A., Nenajdenko, Valentine G., Postnikov, Pavel S., Saito, Akio, Yusubov, Mekhman S., Yoshimura, Akira
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9229713/
https://www.ncbi.nlm.nih.gov/pubmed/35744982
http://dx.doi.org/10.3390/molecules27123860
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author Mironova, Irina A.
Nenajdenko, Valentine G.
Postnikov, Pavel S.
Saito, Akio
Yusubov, Mekhman S.
Yoshimura, Akira
author_facet Mironova, Irina A.
Nenajdenko, Valentine G.
Postnikov, Pavel S.
Saito, Akio
Yusubov, Mekhman S.
Yoshimura, Akira
author_sort Mironova, Irina A.
collection PubMed
description The intramolecular oxidative cycloaddition reaction of alkyne- or alkene-tethered aldoximes was catalyzed efficiently by hypervalent iodine(III) species to afford the corresponding polycyclic isoxazole derivatives in up to a 94% yield. The structure of the prepared products was confirmed by various methods, including X-ray crystallography. Mechanistic study demonstrated the crucial role of hydroxy(aryl)iodonium tosylate as a precatalyst, which is generated from 2-iodobenzoic acid and m-chloroperoxybenzoic acid in the presence of a catalytic amount of p-toluenesulfonic acid.
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spelling pubmed-92297132022-06-25 Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes Mironova, Irina A. Nenajdenko, Valentine G. Postnikov, Pavel S. Saito, Akio Yusubov, Mekhman S. Yoshimura, Akira Molecules Article The intramolecular oxidative cycloaddition reaction of alkyne- or alkene-tethered aldoximes was catalyzed efficiently by hypervalent iodine(III) species to afford the corresponding polycyclic isoxazole derivatives in up to a 94% yield. The structure of the prepared products was confirmed by various methods, including X-ray crystallography. Mechanistic study demonstrated the crucial role of hydroxy(aryl)iodonium tosylate as a precatalyst, which is generated from 2-iodobenzoic acid and m-chloroperoxybenzoic acid in the presence of a catalytic amount of p-toluenesulfonic acid. MDPI 2022-06-16 /pmc/articles/PMC9229713/ /pubmed/35744982 http://dx.doi.org/10.3390/molecules27123860 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
Mironova, Irina A.
Nenajdenko, Valentine G.
Postnikov, Pavel S.
Saito, Akio
Yusubov, Mekhman S.
Yoshimura, Akira
Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes
title Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes
title_full Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes
title_fullStr Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes
title_full_unstemmed Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes
title_short Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes
title_sort efficient catalytic synthesis of condensed isoxazole derivatives via intramolecular oxidative cycloaddition of aldoximes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9229713/
https://www.ncbi.nlm.nih.gov/pubmed/35744982
http://dx.doi.org/10.3390/molecules27123860
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