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An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis
2-Aroylmethylidene-1,2,3,4-tetrahydroquinolines with the appropriate substituents can be suitable precursors for the synthesis of alkaloids from Galipea officinalis (cuspareine, galipeine, galipinine, angustureine). However, only two, rather low-yielding procedures for their synthesis are described...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4464440/ https://www.ncbi.nlm.nih.gov/pubmed/26124890 http://dx.doi.org/10.3762/bjoc.11.99 |
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author | Doušová, Hana Horák, Radim Růžičková, Zdeňka Šimůnek, Petr |
author_facet | Doušová, Hana Horák, Radim Růžičková, Zdeňka Šimůnek, Petr |
author_sort | Doušová, Hana |
collection | PubMed |
description | 2-Aroylmethylidene-1,2,3,4-tetrahydroquinolines with the appropriate substituents can be suitable precursors for the synthesis of alkaloids from Galipea officinalis (cuspareine, galipeine, galipinine, angustureine). However, only two, rather low-yielding procedures for their synthesis are described in the literature. We have developed a simple and efficient protocol for an intramolecular, palladium or copper-catalysed amination of both chloro- and bromo-substituted 3-amino-1,5-diphenylpent-2-en-1-ones leading to the above-mentioned tetrahydroquinoline moiety. The methodology is superior to the methods published to date. |
format | Online Article Text |
id | pubmed-4464440 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-44644402015-06-29 An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis Doušová, Hana Horák, Radim Růžičková, Zdeňka Šimůnek, Petr Beilstein J Org Chem Full Research Paper 2-Aroylmethylidene-1,2,3,4-tetrahydroquinolines with the appropriate substituents can be suitable precursors for the synthesis of alkaloids from Galipea officinalis (cuspareine, galipeine, galipinine, angustureine). However, only two, rather low-yielding procedures for their synthesis are described in the literature. We have developed a simple and efficient protocol for an intramolecular, palladium or copper-catalysed amination of both chloro- and bromo-substituted 3-amino-1,5-diphenylpent-2-en-1-ones leading to the above-mentioned tetrahydroquinoline moiety. The methodology is superior to the methods published to date. Beilstein-Institut 2015-05-27 /pmc/articles/PMC4464440/ /pubmed/26124890 http://dx.doi.org/10.3762/bjoc.11.99 Text en Copyright © 2015, Doušová 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 Doušová, Hana Horák, Radim Růžičková, Zdeňka Šimůnek, Petr An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis |
title | An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis |
title_full | An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis |
title_fullStr | An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis |
title_full_unstemmed | An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis |
title_short | An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis |
title_sort | intramolecular c–n cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of galipea officinalis |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4464440/ https://www.ncbi.nlm.nih.gov/pubmed/26124890 http://dx.doi.org/10.3762/bjoc.11.99 |
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