Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane

Triethylborane (TEB) was found to be a mild, efficient, and acid catalyst in electrophilic substitution reaction of indoles with aldehydes compounds to afford the corresponding bis(indolyl)methanes. Vibrindole A (5) and bis(indolyl)methanes derivatives 16 and 18 were synthesized using this methodolo...

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Autores principales: Merinos, J. Pablo García, Ruíz, Heraclio López, López, Yliana, Lima, Susana Rojas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Bentham Science Publishers 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4475781/
https://www.ncbi.nlm.nih.gov/pubmed/26120289
http://dx.doi.org/10.2174/1570178612666150220225335
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author Merinos, J. Pablo García
Ruíz, Heraclio López
López, Yliana
Lima, Susana Rojas
author_facet Merinos, J. Pablo García
Ruíz, Heraclio López
López, Yliana
Lima, Susana Rojas
author_sort Merinos, J. Pablo García
collection PubMed
description Triethylborane (TEB) was found to be a mild, efficient, and acid catalyst in electrophilic substitution reaction of indoles with aldehydes compounds to afford the corresponding bis(indolyl)methanes. Vibrindole A (5) and bis(indolyl)methanes derivatives 16 and 18 were synthesized using this methodology. Compound 16 is an intermediary in the synthesis of the natural bisindoles arsindoline B (2) and streptindole (6). The structure of vibrindole A (5) was unequivocally confirmed by a single crystal X-ray diffraction analysis.
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spelling pubmed-44757812015-06-24 Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane Merinos, J. Pablo García Ruíz, Heraclio López López, Yliana Lima, Susana Rojas Lett Org Chem Article Triethylborane (TEB) was found to be a mild, efficient, and acid catalyst in electrophilic substitution reaction of indoles with aldehydes compounds to afford the corresponding bis(indolyl)methanes. Vibrindole A (5) and bis(indolyl)methanes derivatives 16 and 18 were synthesized using this methodology. Compound 16 is an intermediary in the synthesis of the natural bisindoles arsindoline B (2) and streptindole (6). The structure of vibrindole A (5) was unequivocally confirmed by a single crystal X-ray diffraction analysis. Bentham Science Publishers 2015-06 2015-06 /pmc/articles/PMC4475781/ /pubmed/26120289 http://dx.doi.org/10.2174/1570178612666150220225335 Text en © 2015 Bentham Science Publishers http://creativecommons.org/licenses/by-nc/3.0/ This is an open access article licensed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted, non-commercial use, distribution and reproduction in any medium, provided the work is properly cited.
spellingShingle Article
Merinos, J. Pablo García
Ruíz, Heraclio López
López, Yliana
Lima, Susana Rojas
Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane
title Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane
title_full Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane
title_fullStr Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane
title_full_unstemmed Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane
title_short Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane
title_sort synthesis of bis(indolyl)methanes catalyzed by triethylborane
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4475781/
https://www.ncbi.nlm.nih.gov/pubmed/26120289
http://dx.doi.org/10.2174/1570178612666150220225335
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