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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...

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Detalles Bibliográficos
Autores principales: Doušová, Hana, Horák, Radim, Růžičková, Zdeňka, Šimůnek, Petr
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
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.
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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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