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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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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. |
format | Online Article Text |
id | pubmed-9735505 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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