Vinylation of N-Heteroarenes through Addition/Elimination Reactions of Vinyl Selenones

A new protocol for the synthesis of N-vinyl azoles using vinyl selenones and azoles in the presence of potassium hydroxide was developed. This reaction proceeded under mild and transition metal-free conditions through an addition/elimination cascade process. Both aromatic and aliphatic vinyl selenon...

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Detalles Bibliográficos
Autores principales: Palomba, Martina, Dias, Italo Franco Coelho, Cocchioni, Michelangelo, Marini, Francesca, Santi, Claudio, Bagnoli, Luana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10459632/
https://www.ncbi.nlm.nih.gov/pubmed/37630278
http://dx.doi.org/10.3390/molecules28166026
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author Palomba, Martina
Dias, Italo Franco Coelho
Cocchioni, Michelangelo
Marini, Francesca
Santi, Claudio
Bagnoli, Luana
author_facet Palomba, Martina
Dias, Italo Franco Coelho
Cocchioni, Michelangelo
Marini, Francesca
Santi, Claudio
Bagnoli, Luana
author_sort Palomba, Martina
collection PubMed
description A new protocol for the synthesis of N-vinyl azoles using vinyl selenones and azoles in the presence of potassium hydroxide was developed. This reaction proceeded under mild and transition metal-free conditions through an addition/elimination cascade process. Both aromatic and aliphatic vinyl selenones and various mono-, bi- and tri-cyclic azoles can be tolerated and give terminal N-vinyl azoles in moderate to high yields. A plausible mechanism is also proposed.
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spelling pubmed-104596322023-08-27 Vinylation of N-Heteroarenes through Addition/Elimination Reactions of Vinyl Selenones Palomba, Martina Dias, Italo Franco Coelho Cocchioni, Michelangelo Marini, Francesca Santi, Claudio Bagnoli, Luana Molecules Article A new protocol for the synthesis of N-vinyl azoles using vinyl selenones and azoles in the presence of potassium hydroxide was developed. This reaction proceeded under mild and transition metal-free conditions through an addition/elimination cascade process. Both aromatic and aliphatic vinyl selenones and various mono-, bi- and tri-cyclic azoles can be tolerated and give terminal N-vinyl azoles in moderate to high yields. A plausible mechanism is also proposed. MDPI 2023-08-12 /pmc/articles/PMC10459632/ /pubmed/37630278 http://dx.doi.org/10.3390/molecules28166026 Text en © 2023 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
Palomba, Martina
Dias, Italo Franco Coelho
Cocchioni, Michelangelo
Marini, Francesca
Santi, Claudio
Bagnoli, Luana
Vinylation of N-Heteroarenes through Addition/Elimination Reactions of Vinyl Selenones
title Vinylation of N-Heteroarenes through Addition/Elimination Reactions of Vinyl Selenones
title_full Vinylation of N-Heteroarenes through Addition/Elimination Reactions of Vinyl Selenones
title_fullStr Vinylation of N-Heteroarenes through Addition/Elimination Reactions of Vinyl Selenones
title_full_unstemmed Vinylation of N-Heteroarenes through Addition/Elimination Reactions of Vinyl Selenones
title_short Vinylation of N-Heteroarenes through Addition/Elimination Reactions of Vinyl Selenones
title_sort vinylation of n-heteroarenes through addition/elimination reactions of vinyl selenones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10459632/
https://www.ncbi.nlm.nih.gov/pubmed/37630278
http://dx.doi.org/10.3390/molecules28166026
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