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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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Autores principales: Bonnaterre, Florence, Bois-Choussy, Michèle, Zhu, Jieping
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2008
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.
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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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