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Synthesis of Substituted Tetrahydroindoloisoquinoline Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination Reactions
[Image: see text] Intramolecular Pd-catalyzed alkene carboamination reactions of substituted 2-allyl-N-(2-bromobenzyl)anilines are described. The substrates for these reactions are generated in two steps from readily available 2-allylanilines and 2-bromobenzaldehyde derivatives. The transformations...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4011572/ https://www.ncbi.nlm.nih.gov/pubmed/24724560 http://dx.doi.org/10.1021/jo500470m |
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author | Alicea, Jeremiah Wolfe, John P. |
author_facet | Alicea, Jeremiah Wolfe, John P. |
author_sort | Alicea, Jeremiah |
collection | PubMed |
description | [Image: see text] Intramolecular Pd-catalyzed alkene carboamination reactions of substituted 2-allyl-N-(2-bromobenzyl)anilines are described. The substrates for these reactions are generated in two steps from readily available 2-allylanilines and 2-bromobenzaldehyde derivatives. The transformations afford substituted tetrahydroindoloisoquinolines, an uncommon class of fused bicyclic heterocycles, in good yield. The mechanism of these transformations is described, and a model that accounts for the observed product stereochemistry is proposed. |
format | Online Article Text |
id | pubmed-4011572 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-40115722015-04-11 Synthesis of Substituted Tetrahydroindoloisoquinoline Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination Reactions Alicea, Jeremiah Wolfe, John P. J Org Chem [Image: see text] Intramolecular Pd-catalyzed alkene carboamination reactions of substituted 2-allyl-N-(2-bromobenzyl)anilines are described. The substrates for these reactions are generated in two steps from readily available 2-allylanilines and 2-bromobenzaldehyde derivatives. The transformations afford substituted tetrahydroindoloisoquinolines, an uncommon class of fused bicyclic heterocycles, in good yield. The mechanism of these transformations is described, and a model that accounts for the observed product stereochemistry is proposed. American Chemical Society 2014-04-11 2014-05-02 /pmc/articles/PMC4011572/ /pubmed/24724560 http://dx.doi.org/10.1021/jo500470m Text en Copyright © 2014 American Chemical Society |
spellingShingle | Alicea, Jeremiah Wolfe, John P. Synthesis of Substituted Tetrahydroindoloisoquinoline Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination Reactions |
title | Synthesis of Substituted Tetrahydroindoloisoquinoline
Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination
Reactions |
title_full | Synthesis of Substituted Tetrahydroindoloisoquinoline
Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination
Reactions |
title_fullStr | Synthesis of Substituted Tetrahydroindoloisoquinoline
Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination
Reactions |
title_full_unstemmed | Synthesis of Substituted Tetrahydroindoloisoquinoline
Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination
Reactions |
title_short | Synthesis of Substituted Tetrahydroindoloisoquinoline
Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination
Reactions |
title_sort | synthesis of substituted tetrahydroindoloisoquinoline
derivatives via intramolecular pd-catalyzed alkene carboamination
reactions |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4011572/ https://www.ncbi.nlm.nih.gov/pubmed/24724560 http://dx.doi.org/10.1021/jo500470m |
work_keys_str_mv | AT aliceajeremiah synthesisofsubstitutedtetrahydroindoloisoquinolinederivativesviaintramolecularpdcatalyzedalkenecarboaminationreactions AT wolfejohnp synthesisofsubstitutedtetrahydroindoloisoquinolinederivativesviaintramolecularpdcatalyzedalkenecarboaminationreactions |