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Synthesis of dihydrophenanthridines by a sequence of Ugi-4CR and palladium-catalyzed intramolecular C-H functionalization
BACKGROUND: Small polyfunctionalized heterocyclic compounds play important roles in the drug discovery process and in the isolation and structural identification of biological macromolecules. It is expected that ready access to diverse sets of heterocycles can not only help improving the known biolo...
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Formato: | Texto |
Lenguaje: | English |
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Beilstein-Institut
2008
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2395297/ https://www.ncbi.nlm.nih.gov/pubmed/18665200 http://dx.doi.org/10.3762/bjoc.4.10 |
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author | Bonnaterre, Florence Bois-Choussy, Michèle Zhu, Jieping |
author_facet | Bonnaterre, Florence Bois-Choussy, Michèle Zhu, Jieping |
author_sort | Bonnaterre, Florence |
collection | PubMed |
description | BACKGROUND: Small polyfunctionalized heterocyclic compounds play important roles in the drug discovery process and in the isolation and structural identification of biological macromolecules. It is expected that ready access to diverse sets of heterocycles can not only help improving the known biological and pharmacokinetic properties of drugs, but also assist the discovery of molecules that exhibit biological effects beyond those associated with previously known macromolecules. By virtue of their inherent convergence, high productivity, their exploratory and complexity-generating power, multicomponent reactions (MCRs) are undoubtedly well suited for creating molecular diversity. The combination of MCRs with an efficient post-functionalization reaction has proven to be an efficient strategy to increase the skeleton diversity. RESULTS: The Ugi reaction of an o-iodobenzaldehyde (2), an aniline (3), an isocyanide (4), and a carboxylic acid (5) afforded α-acetamido-α-phenylacetamide (6) in good to excellent yields. The palladium-catalyzed intramolecular C-H functionalization of these adducts under ligandless conditions provided the functionalized dihydrophenanthridines (1). CONCLUSION: Highly functionalized dihydrophenanthridines are synthesized in only two steps from readily accessible starting materials in good to excellent overall yields. |
format | Text |
id | pubmed-2395297 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-23952972008-07-29 Synthesis of dihydrophenanthridines by a sequence of Ugi-4CR and palladium-catalyzed intramolecular C-H functionalization Bonnaterre, Florence Bois-Choussy, Michèle Zhu, Jieping Beilstein J Org Chem Full Research Paper BACKGROUND: Small polyfunctionalized heterocyclic compounds play important roles in the drug discovery process and in the isolation and structural identification of biological macromolecules. It is expected that ready access to diverse sets of heterocycles can not only help improving the known biological and pharmacokinetic properties of drugs, but also assist the discovery of molecules that exhibit biological effects beyond those associated with previously known macromolecules. By virtue of their inherent convergence, high productivity, their exploratory and complexity-generating power, multicomponent reactions (MCRs) are undoubtedly well suited for creating molecular diversity. The combination of MCRs with an efficient post-functionalization reaction has proven to be an efficient strategy to increase the skeleton diversity. RESULTS: The Ugi reaction of an o-iodobenzaldehyde (2), an aniline (3), an isocyanide (4), and a carboxylic acid (5) afforded α-acetamido-α-phenylacetamide (6) in good to excellent yields. The palladium-catalyzed intramolecular C-H functionalization of these adducts under ligandless conditions provided the functionalized dihydrophenanthridines (1). CONCLUSION: Highly functionalized dihydrophenanthridines are synthesized in only two steps from readily accessible starting materials in good to excellent overall yields. Beilstein-Institut 2008-04-08 /pmc/articles/PMC2395297/ /pubmed/18665200 http://dx.doi.org/10.3762/bjoc.4.10 Text en Copyright © 2008, Bonnaterre 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 Bonnaterre, Florence Bois-Choussy, Michèle Zhu, Jieping Synthesis of dihydrophenanthridines by a sequence of Ugi-4CR and palladium-catalyzed intramolecular C-H functionalization |
title | Synthesis of dihydrophenanthridines by a sequence of Ugi-4CR and palladium-catalyzed intramolecular C-H functionalization |
title_full | Synthesis of dihydrophenanthridines by a sequence of Ugi-4CR and palladium-catalyzed intramolecular C-H functionalization |
title_fullStr | Synthesis of dihydrophenanthridines by a sequence of Ugi-4CR and palladium-catalyzed intramolecular C-H functionalization |
title_full_unstemmed | Synthesis of dihydrophenanthridines by a sequence of Ugi-4CR and palladium-catalyzed intramolecular C-H functionalization |
title_short | Synthesis of dihydrophenanthridines by a sequence of Ugi-4CR and palladium-catalyzed intramolecular C-H functionalization |
title_sort | synthesis of dihydrophenanthridines by a sequence of ugi-4cr and palladium-catalyzed intramolecular c-h functionalization |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2395297/ https://www.ncbi.nlm.nih.gov/pubmed/18665200 http://dx.doi.org/10.3762/bjoc.4.10 |
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