The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights

New insights concerning the reaction mechanism in the cycloaddition reaction of benzimidazolium ylides to activated alkynes are presented. The proposed pathway leading both to 2-(1H-pyrrol-1-yl)anilines and to pyrrolo[1,2-a]quinoxalin-4(5H)-ones involves an opening of the imidazole ring from the cyc...

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Autores principales: Moldoveanu, Costel, Zbancioc, Gheorghita, Mantu, Dorina, Maftei, Dan, Mangalagiu, Ionel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2016
Materias:
Research Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4880325/
https://www.ncbi.nlm.nih.gov/pubmed/27224656
http://dx.doi.org/10.1371/journal.pone.0156129
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author Moldoveanu, Costel
Zbancioc, Gheorghita
Mantu, Dorina
Maftei, Dan
Mangalagiu, Ionel
author_facet Moldoveanu, Costel
Zbancioc, Gheorghita
Mantu, Dorina
Maftei, Dan
Mangalagiu, Ionel
author_sort Moldoveanu, Costel
collection PubMed
description New insights concerning the reaction mechanism in the cycloaddition reaction of benzimidazolium ylides to activated alkynes are presented. The proposed pathway leading both to 2-(1H-pyrrol-1-yl)anilines and to pyrrolo[1,2-a]quinoxalin-4(5H)-ones involves an opening of the imidazole ring from the cycloaddition product, followed by a nucleophilic attack of the aminic nitrogen to a proximal carbonyl group and the elimination of a leaving group. The mechanistic considerations are fully supported by experimental data, including the XRD resolved structure of the key reaction intermediate.
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spelling pubmed-48803252016-06-09 The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights Moldoveanu, Costel Zbancioc, Gheorghita Mantu, Dorina Maftei, Dan Mangalagiu, Ionel PLoS One Research Article New insights concerning the reaction mechanism in the cycloaddition reaction of benzimidazolium ylides to activated alkynes are presented. The proposed pathway leading both to 2-(1H-pyrrol-1-yl)anilines and to pyrrolo[1,2-a]quinoxalin-4(5H)-ones involves an opening of the imidazole ring from the cycloaddition product, followed by a nucleophilic attack of the aminic nitrogen to a proximal carbonyl group and the elimination of a leaving group. The mechanistic considerations are fully supported by experimental data, including the XRD resolved structure of the key reaction intermediate. Public Library of Science 2016-05-25 /pmc/articles/PMC4880325/ /pubmed/27224656 http://dx.doi.org/10.1371/journal.pone.0156129 Text en © 2016 Moldoveanu et al http://creativecommons.org/licenses/by/4.0/ This is an open access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) , which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
spellingShingle Research Article
Moldoveanu, Costel
Zbancioc, Gheorghita
Mantu, Dorina
Maftei, Dan
Mangalagiu, Ionel
The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights
title The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights
title_full The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights
title_fullStr The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights
title_full_unstemmed The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights
title_short The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights
title_sort cycloaddition of the benzimidazolium ylides with alkynes: new mechanistic insights
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4880325/
https://www.ncbi.nlm.nih.gov/pubmed/27224656
http://dx.doi.org/10.1371/journal.pone.0156129
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