<i>N</i>-Arylation of 3-Formylquinolin-2(1<i>H</i>)-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 <i>N&l...
| Published in: | Molecules |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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MDPI AG
2022-11-01
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| Online Access: | https://www.mdpi.com/1420-3049/27/23/8345 |
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| author | Jhesua Valencia Oriel A. Sánchez-Velasco Jorge Saavedra-Olavarría Patricio Hermosilla-Ibáñez Edwin G. Pérez Daniel Insuasty |
| author_facet | Jhesua Valencia Oriel A. Sánchez-Velasco Jorge Saavedra-Olavarría Patricio Hermosilla-Ibáñez Edwin G. Pérez Daniel Insuasty |
| author_sort | Jhesua Valencia |
| collection | DOAJ |
| container_title | Molecules |
| 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 <i>N</i>-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 <i>p</i>-methyl derivative <b>9a</b> was used as a substrate to obtain different derivatives such as alcohol, amine, nitrile, and chalcone. |
| format | Article |
| id | doaj-art-b3df1cb2f50d48a088b30f2d4e9cc525 |
| institution | Directory of Open Access Journals |
| issn | 1420-3049 |
| language | English |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| spelling | doaj-art-b3df1cb2f50d48a088b30f2d4e9cc5252025-08-19T22:39:24ZengMDPI AGMolecules1420-30492022-11-012723834510.3390/molecules27238345<i>N</i>-Arylation of 3-Formylquinolin-2(1<i>H</i>)-ones Using Copper(II)-Catalyzed Chan–Lam CouplingJhesua Valencia0Oriel A. Sánchez-Velasco1Jorge Saavedra-Olavarría2Patricio Hermosilla-Ibáñez3Edwin G. Pérez4Daniel Insuasty5Departamento de Química y Biología, División de Ciencias Básicas, Universidad del Norte, Km 5 Vía Puerto Colombia, Barranquilla 081007, ColombiaDepartment of Organic Chemistry, Faculty of Chemistry and Pharmacy, Pontificia Universidad Católica de Chile, Santiago 7820436, ChileDepartment of Organic Chemistry, Faculty of Chemistry and Pharmacy, Pontificia Universidad Católica de Chile, Santiago 7820436, ChileCenter for the Development of Nanoscience and Nanotechnology (CEDENNA), Materials Chemistry Department, Faculty of Chemistry and Biology, University of Santiago, Chile, Santiago 9170022, ChileDepartment of Organic Chemistry, Faculty of Chemistry and Pharmacy, Pontificia Universidad Católica de Chile, Santiago 7820436, ChileDepartamento de Química y Biología, División de Ciencias Básicas, Universidad del Norte, Km 5 Vía Puerto Colombia, Barranquilla 081007, Colombia3-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 <i>N</i>-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 <i>p</i>-methyl derivative <b>9a</b> was used as a substrate to obtain different derivatives such as alcohol, amine, nitrile, and chalcone.https://www.mdpi.com/1420-3049/27/23/8345Chan–Lam couplingcopper(II)<i>N</i>-arylation3-formylquinolones |
| spellingShingle | Jhesua Valencia Oriel A. Sánchez-Velasco Jorge Saavedra-Olavarría Patricio Hermosilla-Ibáñez Edwin G. Pérez Daniel Insuasty <i>N</i>-Arylation of 3-Formylquinolin-2(1<i>H</i>)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling Chan–Lam coupling copper(II) <i>N</i>-arylation 3-formylquinolones |
| title | <i>N</i>-Arylation of 3-Formylquinolin-2(1<i>H</i>)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling |
| title_full | <i>N</i>-Arylation of 3-Formylquinolin-2(1<i>H</i>)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling |
| title_fullStr | <i>N</i>-Arylation of 3-Formylquinolin-2(1<i>H</i>)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling |
| title_full_unstemmed | <i>N</i>-Arylation of 3-Formylquinolin-2(1<i>H</i>)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling |
| title_short | <i>N</i>-Arylation of 3-Formylquinolin-2(1<i>H</i>)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling |
| title_sort | i n i arylation of 3 formylquinolin 2 1 i h i ones using copper ii catalyzed chan lam coupling |
| topic | Chan–Lam coupling copper(II) <i>N</i>-arylation 3-formylquinolones |
| url | https://www.mdpi.com/1420-3049/27/23/8345 |
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