Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF(3)-α-Amino Carboxylates

A convenient pathway to a new series of α-CF(3)-substituted α-amino acid derivatives bearing pharmacophore isoquinolone core in their backbone has been developed. The method is based on [4+2]-annulation of N-(pivaloyloxy) aryl amides with orthogonally protected internal acetylene-containing α-amino...

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Autores principales: Vorobyeva, Daria V., Petropavlovskikh, Dmitry A., Godovikov, Ivan A., Dolgushin, Fedor M., Osipov, Sergey N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9736582/
https://www.ncbi.nlm.nih.gov/pubmed/36500580
http://dx.doi.org/10.3390/molecules27238488
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author Vorobyeva, Daria V.
Petropavlovskikh, Dmitry A.
Godovikov, Ivan A.
Dolgushin, Fedor M.
Osipov, Sergey N.
author_facet Vorobyeva, Daria V.
Petropavlovskikh, Dmitry A.
Godovikov, Ivan A.
Dolgushin, Fedor M.
Osipov, Sergey N.
author_sort Vorobyeva, Daria V.
collection PubMed
description A convenient pathway to a new series of α-CF(3)-substituted α-amino acid derivatives bearing pharmacophore isoquinolone core in their backbone has been developed. The method is based on [4+2]-annulation of N-(pivaloyloxy) aryl amides with orthogonally protected internal acetylene-containing α-amino carboxylates under Rh(III)-catalysis. The target annulation products can be easily transformed into valuable isoquinoline derivatives via a successive aromatization/cross-coupling operation.
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spelling pubmed-97365822022-12-11 Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF(3)-α-Amino Carboxylates Vorobyeva, Daria V. Petropavlovskikh, Dmitry A. Godovikov, Ivan A. Dolgushin, Fedor M. Osipov, Sergey N. Molecules Article A convenient pathway to a new series of α-CF(3)-substituted α-amino acid derivatives bearing pharmacophore isoquinolone core in their backbone has been developed. The method is based on [4+2]-annulation of N-(pivaloyloxy) aryl amides with orthogonally protected internal acetylene-containing α-amino carboxylates under Rh(III)-catalysis. The target annulation products can be easily transformed into valuable isoquinoline derivatives via a successive aromatization/cross-coupling operation. MDPI 2022-12-02 /pmc/articles/PMC9736582/ /pubmed/36500580 http://dx.doi.org/10.3390/molecules27238488 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
Vorobyeva, Daria V.
Petropavlovskikh, Dmitry A.
Godovikov, Ivan A.
Dolgushin, Fedor M.
Osipov, Sergey N.
Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF(3)-α-Amino Carboxylates
title Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF(3)-α-Amino Carboxylates
title_full Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF(3)-α-Amino Carboxylates
title_fullStr Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF(3)-α-Amino Carboxylates
title_full_unstemmed Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF(3)-α-Amino Carboxylates
title_short Synthesis of Functionalized Isoquinolone Derivatives via Rh(III)-Catalyzed [4+2]-Annulation of Benzamides with Internal Acetylene-Containing α-CF(3)-α-Amino Carboxylates
title_sort synthesis of functionalized isoquinolone derivatives via rh(iii)-catalyzed [4+2]-annulation of benzamides with internal acetylene-containing α-cf(3)-α-amino carboxylates
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9736582/
https://www.ncbi.nlm.nih.gov/pubmed/36500580
http://dx.doi.org/10.3390/molecules27238488
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