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Gold(I)-Catalyzed Reactivity of Furan-ynes with N-Oxides: Synthesis of Substituted Dihydropyridinones and Pyranones

[Image: see text] The reactivity of “furan-ynes” in combination with pyridine and quinoline N-oxides in the presence of a Au(I) catalyst, has been studied, enabling the synthesis of three different heterocyclic scaffolds. Selective access to two out of the three possible products, a dihydropyridinon...

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Autores principales: Nejrotti, Stefano, Marra, Francesco, Priola, Emanuele, Maranzana, Andrea, Prandi, Cristina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8279485/
https://www.ncbi.nlm.nih.gov/pubmed/34100288
http://dx.doi.org/10.1021/acs.joc.1c00746
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author Nejrotti, Stefano
Marra, Francesco
Priola, Emanuele
Maranzana, Andrea
Prandi, Cristina
author_facet Nejrotti, Stefano
Marra, Francesco
Priola, Emanuele
Maranzana, Andrea
Prandi, Cristina
author_sort Nejrotti, Stefano
collection PubMed
description [Image: see text] The reactivity of “furan-ynes” in combination with pyridine and quinoline N-oxides in the presence of a Au(I) catalyst, has been studied, enabling the synthesis of three different heterocyclic scaffolds. Selective access to two out of the three possible products, a dihydropyridinone and a furan enone, has been achieved through the fine-tuning of the reaction conditions. The reactions proceed smoothly at room temperature and open-air, and were further extended to a broad substrate scope, thus affording functionalized dihydropyridinones and pyranones.
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spelling pubmed-82794852021-07-15 Gold(I)-Catalyzed Reactivity of Furan-ynes with N-Oxides: Synthesis of Substituted Dihydropyridinones and Pyranones Nejrotti, Stefano Marra, Francesco Priola, Emanuele Maranzana, Andrea Prandi, Cristina J Org Chem [Image: see text] The reactivity of “furan-ynes” in combination with pyridine and quinoline N-oxides in the presence of a Au(I) catalyst, has been studied, enabling the synthesis of three different heterocyclic scaffolds. Selective access to two out of the three possible products, a dihydropyridinone and a furan enone, has been achieved through the fine-tuning of the reaction conditions. The reactions proceed smoothly at room temperature and open-air, and were further extended to a broad substrate scope, thus affording functionalized dihydropyridinones and pyranones. American Chemical Society 2021-06-08 2021-06-18 /pmc/articles/PMC8279485/ /pubmed/34100288 http://dx.doi.org/10.1021/acs.joc.1c00746 Text en © 2021 The Authors. Published by American Chemical Society Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Nejrotti, Stefano
Marra, Francesco
Priola, Emanuele
Maranzana, Andrea
Prandi, Cristina
Gold(I)-Catalyzed Reactivity of Furan-ynes with N-Oxides: Synthesis of Substituted Dihydropyridinones and Pyranones
title Gold(I)-Catalyzed Reactivity of Furan-ynes with N-Oxides: Synthesis of Substituted Dihydropyridinones and Pyranones
title_full Gold(I)-Catalyzed Reactivity of Furan-ynes with N-Oxides: Synthesis of Substituted Dihydropyridinones and Pyranones
title_fullStr Gold(I)-Catalyzed Reactivity of Furan-ynes with N-Oxides: Synthesis of Substituted Dihydropyridinones and Pyranones
title_full_unstemmed Gold(I)-Catalyzed Reactivity of Furan-ynes with N-Oxides: Synthesis of Substituted Dihydropyridinones and Pyranones
title_short Gold(I)-Catalyzed Reactivity of Furan-ynes with N-Oxides: Synthesis of Substituted Dihydropyridinones and Pyranones
title_sort gold(i)-catalyzed reactivity of furan-ynes with n-oxides: synthesis of substituted dihydropyridinones and pyranones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8279485/
https://www.ncbi.nlm.nih.gov/pubmed/34100288
http://dx.doi.org/10.1021/acs.joc.1c00746
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