An organocatalytic route to 2-heteroarylmethylene decorated N-arylpyrroles

A concise and regioselective preparation of 2-heteroarylmethylene decorated N-arylpyrroles is described through a metal-free Mannich/Wittig/hydroamination sequence followed by isomerization of the N-arylpyrrolidine adducts. Furthermore, the C–H regioselective oxidation of these substrates is demonst...

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Detalles Bibliográficos
Autores principales: Jean, Alexandre, Blanchet, Jérôme, Rouden, Jacques, Maddaluno, Jacques, De Paolis, Michaël
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3740684/
https://www.ncbi.nlm.nih.gov/pubmed/23946846
http://dx.doi.org/10.3762/bjoc.9.168
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author Jean, Alexandre
Blanchet, Jérôme
Rouden, Jacques
Maddaluno, Jacques
De Paolis, Michaël
author_facet Jean, Alexandre
Blanchet, Jérôme
Rouden, Jacques
Maddaluno, Jacques
De Paolis, Michaël
author_sort Jean, Alexandre
collection PubMed
description A concise and regioselective preparation of 2-heteroarylmethylene decorated N-arylpyrroles is described through a metal-free Mannich/Wittig/hydroamination sequence followed by isomerization of the N-arylpyrrolidine adducts. Furthermore, the C–H regioselective oxidation of these substrates is demonstrated, extending the molecular diversity and versatility of these scaffolds.
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spelling pubmed-37406842013-08-14 An organocatalytic route to 2-heteroarylmethylene decorated N-arylpyrroles Jean, Alexandre Blanchet, Jérôme Rouden, Jacques Maddaluno, Jacques De Paolis, Michaël Beilstein J Org Chem Full Research Paper A concise and regioselective preparation of 2-heteroarylmethylene decorated N-arylpyrroles is described through a metal-free Mannich/Wittig/hydroamination sequence followed by isomerization of the N-arylpyrrolidine adducts. Furthermore, the C–H regioselective oxidation of these substrates is demonstrated, extending the molecular diversity and versatility of these scaffolds. Beilstein-Institut 2013-07-24 /pmc/articles/PMC3740684/ /pubmed/23946846 http://dx.doi.org/10.3762/bjoc.9.168 Text en Copyright © 2013, Jean et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Jean, Alexandre
Blanchet, Jérôme
Rouden, Jacques
Maddaluno, Jacques
De Paolis, Michaël
An organocatalytic route to 2-heteroarylmethylene decorated N-arylpyrroles
title An organocatalytic route to 2-heteroarylmethylene decorated N-arylpyrroles
title_full An organocatalytic route to 2-heteroarylmethylene decorated N-arylpyrroles
title_fullStr An organocatalytic route to 2-heteroarylmethylene decorated N-arylpyrroles
title_full_unstemmed An organocatalytic route to 2-heteroarylmethylene decorated N-arylpyrroles
title_short An organocatalytic route to 2-heteroarylmethylene decorated N-arylpyrroles
title_sort organocatalytic route to 2-heteroarylmethylene decorated n-arylpyrroles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3740684/
https://www.ncbi.nlm.nih.gov/pubmed/23946846
http://dx.doi.org/10.3762/bjoc.9.168
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