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N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling

3-formyl-2-quinolones have attracted the scientific community’s attention because they are used as versatile building blocks in the synthesis of more complex compounds showing different and attractive biological activities. Using copper-catalyzed Chan–Lam coupling, we synthesized 32 new N-aryl-3-for...

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Autores principales: Valencia, Jhesua, Sánchez-Velasco, Oriel A., Saavedra-Olavarría, Jorge, Hermosilla-Ibáñez, Patricio, Pérez, Edwin G., Insuasty, Daniel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9735505/
https://www.ncbi.nlm.nih.gov/pubmed/36500438
http://dx.doi.org/10.3390/molecules27238345
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author Valencia, Jhesua
Sánchez-Velasco, Oriel A.
Saavedra-Olavarría, Jorge
Hermosilla-Ibáñez, Patricio
Pérez, Edwin G.
Insuasty, Daniel
author_facet Valencia, Jhesua
Sánchez-Velasco, Oriel A.
Saavedra-Olavarría, Jorge
Hermosilla-Ibáñez, Patricio
Pérez, Edwin G.
Insuasty, Daniel
author_sort Valencia, Jhesua
collection PubMed
description 3-formyl-2-quinolones have attracted the scientific community’s attention because they are used as versatile building blocks in the synthesis of more complex compounds showing different and attractive biological activities. Using copper-catalyzed Chan–Lam coupling, we synthesized 32 new N-aryl-3-formyl-2-quinolone derivatives at 80 °C, in air and using inexpensive phenylboronic acids as arylating agents. 3-formyl-2-quinolones and substituted 3-formyl-2-quinolones can act as substrates, and among the products, the p-methyl derivative 9a was used as a substrate to obtain different derivatives such as alcohol, amine, nitrile, and chalcone.
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spelling pubmed-97355052022-12-11 N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling Valencia, Jhesua Sánchez-Velasco, Oriel A. Saavedra-Olavarría, Jorge Hermosilla-Ibáñez, Patricio Pérez, Edwin G. Insuasty, Daniel Molecules Article 3-formyl-2-quinolones have attracted the scientific community’s attention because they are used as versatile building blocks in the synthesis of more complex compounds showing different and attractive biological activities. Using copper-catalyzed Chan–Lam coupling, we synthesized 32 new N-aryl-3-formyl-2-quinolone derivatives at 80 °C, in air and using inexpensive phenylboronic acids as arylating agents. 3-formyl-2-quinolones and substituted 3-formyl-2-quinolones can act as substrates, and among the products, the p-methyl derivative 9a was used as a substrate to obtain different derivatives such as alcohol, amine, nitrile, and chalcone. MDPI 2022-11-30 /pmc/articles/PMC9735505/ /pubmed/36500438 http://dx.doi.org/10.3390/molecules27238345 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
Valencia, Jhesua
Sánchez-Velasco, Oriel A.
Saavedra-Olavarría, Jorge
Hermosilla-Ibáñez, Patricio
Pérez, Edwin G.
Insuasty, Daniel
N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling
title N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling
title_full N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling
title_fullStr N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling
title_full_unstemmed N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling
title_short N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling
title_sort n-arylation of 3-formylquinolin-2(1h)-ones using copper(ii)-catalyzed chan–lam coupling
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9735505/
https://www.ncbi.nlm.nih.gov/pubmed/36500438
http://dx.doi.org/10.3390/molecules27238345
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