Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes

In a simple procedure, the intramolecular hydroarylation of N-propargyl-pyrrole-2-carboxamides was accomplished with the aid of gold(III) catalysis. The reaction led to differently substituted pyrrolo[2,3-c]pyridine and pyrrolo[3,2-c]pyridine derivatives arising either from direct cyclization or fro...

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Autores principales: Borsini, Elena, Broggini, Gianluigi, Fasana, Andrea, Baldassarri, Chiara, Manzo, Angelo M, Perboni, Alcide D
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3252845/
https://www.ncbi.nlm.nih.gov/pubmed/22238519
http://dx.doi.org/10.3762/bjoc.7.170
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author Borsini, Elena
Broggini, Gianluigi
Fasana, Andrea
Baldassarri, Chiara
Manzo, Angelo M
Perboni, Alcide D
author_facet Borsini, Elena
Broggini, Gianluigi
Fasana, Andrea
Baldassarri, Chiara
Manzo, Angelo M
Perboni, Alcide D
author_sort Borsini, Elena
collection PubMed
description In a simple procedure, the intramolecular hydroarylation of N-propargyl-pyrrole-2-carboxamides was accomplished with the aid of gold(III) catalysis. The reaction led to differently substituted pyrrolo[2,3-c]pyridine and pyrrolo[3,2-c]pyridine derivatives arising either from direct cyclization or from a formal rearrangement of the carboxamide group. Terminal alkynes are essential to achieve bicyclic pyrrolo-fused pyridinones by a 6-exo-dig process, while the presence of a phenyl group at the C–C triple bond promotes the 7-endo-dig cyclization giving pyrrolo-azepines.
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spelling pubmed-32528452012-01-11 Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes Borsini, Elena Broggini, Gianluigi Fasana, Andrea Baldassarri, Chiara Manzo, Angelo M Perboni, Alcide D Beilstein J Org Chem Full Research Paper In a simple procedure, the intramolecular hydroarylation of N-propargyl-pyrrole-2-carboxamides was accomplished with the aid of gold(III) catalysis. The reaction led to differently substituted pyrrolo[2,3-c]pyridine and pyrrolo[3,2-c]pyridine derivatives arising either from direct cyclization or from a formal rearrangement of the carboxamide group. Terminal alkynes are essential to achieve bicyclic pyrrolo-fused pyridinones by a 6-exo-dig process, while the presence of a phenyl group at the C–C triple bond promotes the 7-endo-dig cyclization giving pyrrolo-azepines. Beilstein-Institut 2011-10-26 /pmc/articles/PMC3252845/ /pubmed/22238519 http://dx.doi.org/10.3762/bjoc.7.170 Text en Copyright © 2011, Borsini 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
Borsini, Elena
Broggini, Gianluigi
Fasana, Andrea
Baldassarri, Chiara
Manzo, Angelo M
Perboni, Alcide D
Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes
title Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes
title_full Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes
title_fullStr Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes
title_full_unstemmed Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes
title_short Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes
title_sort access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3252845/
https://www.ncbi.nlm.nih.gov/pubmed/22238519
http://dx.doi.org/10.3762/bjoc.7.170
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