A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene

A novel, low-cost method for the preparation of not easily accessible free 3-aminoindoles has been developed. This approach is based on a well-established reaction between indoles and nitrostyrene in the presence of phosphorous acid, which results in the formation of 4′-phenyl-4′H-spiro[indole-3,5′-...

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Autores principales: Aksenov, Nicolai A., Arutiunov, Nikolai A., Kurenkov, Igor A., Malyuga, Vladimir V., Aksenov, Dmitrii A., Momotova, Daria S., Zatsepilina, Anna M., Chukanova, Elizaveta A., Leontiev, Alexander V., Aksenov, Alexander V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10180116/
https://www.ncbi.nlm.nih.gov/pubmed/37175067
http://dx.doi.org/10.3390/molecules28093657
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author Aksenov, Nicolai A.
Arutiunov, Nikolai A.
Kurenkov, Igor A.
Malyuga, Vladimir V.
Aksenov, Dmitrii A.
Momotova, Daria S.
Zatsepilina, Anna M.
Chukanova, Elizaveta A.
Leontiev, Alexander V.
Aksenov, Alexander V.
author_facet Aksenov, Nicolai A.
Arutiunov, Nikolai A.
Kurenkov, Igor A.
Malyuga, Vladimir V.
Aksenov, Dmitrii A.
Momotova, Daria S.
Zatsepilina, Anna M.
Chukanova, Elizaveta A.
Leontiev, Alexander V.
Aksenov, Alexander V.
author_sort Aksenov, Nicolai A.
collection PubMed
description A novel, low-cost method for the preparation of not easily accessible free 3-aminoindoles has been developed. This approach is based on a well-established reaction between indoles and nitrostyrene in the presence of phosphorous acid, which results in the formation of 4′-phenyl-4′H-spiro[indole-3,5′-isoxazoles]. The latter could be transformed to corresponding aminated indoles by reaction with hydrazine hydrate in good or excellent yields upon microwave-assisted heating.
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spelling pubmed-101801162023-05-13 A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene Aksenov, Nicolai A. Arutiunov, Nikolai A. Kurenkov, Igor A. Malyuga, Vladimir V. Aksenov, Dmitrii A. Momotova, Daria S. Zatsepilina, Anna M. Chukanova, Elizaveta A. Leontiev, Alexander V. Aksenov, Alexander V. Molecules Article A novel, low-cost method for the preparation of not easily accessible free 3-aminoindoles has been developed. This approach is based on a well-established reaction between indoles and nitrostyrene in the presence of phosphorous acid, which results in the formation of 4′-phenyl-4′H-spiro[indole-3,5′-isoxazoles]. The latter could be transformed to corresponding aminated indoles by reaction with hydrazine hydrate in good or excellent yields upon microwave-assisted heating. MDPI 2023-04-23 /pmc/articles/PMC10180116/ /pubmed/37175067 http://dx.doi.org/10.3390/molecules28093657 Text en © 2023 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
Aksenov, Nicolai A.
Arutiunov, Nikolai A.
Kurenkov, Igor A.
Malyuga, Vladimir V.
Aksenov, Dmitrii A.
Momotova, Daria S.
Zatsepilina, Anna M.
Chukanova, Elizaveta A.
Leontiev, Alexander V.
Aksenov, Alexander V.
A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene
title A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene
title_full A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene
title_fullStr A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene
title_full_unstemmed A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene
title_short A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene
title_sort two-step synthesis of unprotected 3-aminoindoles via post functionalization with nitrostyrene
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10180116/
https://www.ncbi.nlm.nih.gov/pubmed/37175067
http://dx.doi.org/10.3390/molecules28093657
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