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Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

Medium-sized heterocycles (with 8 to 11 atoms) constitute important structural components of several biologically active natural compounds and represent promising scaffolds in medicinal chemistry. However, they are under-represented in the screening of chemical libraries as a consequence of being di...

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Autores principales: Choury, Mickael, Basilio Lopes, Alexandra, Blond, Gaëlle, Gulea, Mihaela
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7397130/
https://www.ncbi.nlm.nih.gov/pubmed/32660105
http://dx.doi.org/10.3390/molecules25143147
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author Choury, Mickael
Basilio Lopes, Alexandra
Blond, Gaëlle
Gulea, Mihaela
author_facet Choury, Mickael
Basilio Lopes, Alexandra
Blond, Gaëlle
Gulea, Mihaela
author_sort Choury, Mickael
collection PubMed
description Medium-sized heterocycles (with 8 to 11 atoms) constitute important structural components of several biologically active natural compounds and represent promising scaffolds in medicinal chemistry. However, they are under-represented in the screening of chemical libraries as a consequence of being difficult to access. In particular, methods involving intramolecular bond formation are challenging due to unfavorable enthalpic and entropic factors, such as transannular interactions and conformational constraints. The present review focuses on the synthesis of medium-sized heterocycles by transition-metal-catalyzed intramolecular cyclization, which despite its drawbacks remains a straightforward and attractive synthesis strategy. The obtained heterocycles differ in their nature, number of heteroatoms, and ring size. The methods are classified according to the metal used (palladium, copper, gold, silver), then subdivided according to the type of bond formed, namely carbon–carbon or carbon–heteroatom.
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spelling pubmed-73971302020-08-05 Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization Choury, Mickael Basilio Lopes, Alexandra Blond, Gaëlle Gulea, Mihaela Molecules Review Medium-sized heterocycles (with 8 to 11 atoms) constitute important structural components of several biologically active natural compounds and represent promising scaffolds in medicinal chemistry. However, they are under-represented in the screening of chemical libraries as a consequence of being difficult to access. In particular, methods involving intramolecular bond formation are challenging due to unfavorable enthalpic and entropic factors, such as transannular interactions and conformational constraints. The present review focuses on the synthesis of medium-sized heterocycles by transition-metal-catalyzed intramolecular cyclization, which despite its drawbacks remains a straightforward and attractive synthesis strategy. The obtained heterocycles differ in their nature, number of heteroatoms, and ring size. The methods are classified according to the metal used (palladium, copper, gold, silver), then subdivided according to the type of bond formed, namely carbon–carbon or carbon–heteroatom. MDPI 2020-07-09 /pmc/articles/PMC7397130/ /pubmed/32660105 http://dx.doi.org/10.3390/molecules25143147 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Choury, Mickael
Basilio Lopes, Alexandra
Blond, Gaëlle
Gulea, Mihaela
Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization
title Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization
title_full Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization
title_fullStr Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization
title_full_unstemmed Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization
title_short Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization
title_sort synthesis of medium-sized heterocycles by transition-metal-catalyzed intramolecular cyclization
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7397130/
https://www.ncbi.nlm.nih.gov/pubmed/32660105
http://dx.doi.org/10.3390/molecules25143147
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