2-Chlorophenyl Zinc Bromide: A Convenient Nucleophile for the Mannich-Related Multicomponent Synthesis of Clopidogrel and Ticlopidine

A methodological study devoted to the Mannich-like multicomponent synthesis of the antiplatelet agent (±)-clopidogrel (7) and the ethyl ester analogue 6 is described. The process involves the formation of 2-chlorophenyl zinc bromide (2) and its subsequent reaction with an alkyl glyoxylate and 4,5,6,...

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Autores principales: Aillaud, Isabelle, Haurena, Caroline, Gall, Erwan Le, Martens, Thierry, Ricci, Gino
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259200/
https://www.ncbi.nlm.nih.gov/pubmed/21072025
http://dx.doi.org/10.3390/molecules15118144
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author Aillaud, Isabelle
Haurena, Caroline
Gall, Erwan Le
Martens, Thierry
Ricci, Gino
author_facet Aillaud, Isabelle
Haurena, Caroline
Gall, Erwan Le
Martens, Thierry
Ricci, Gino
author_sort Aillaud, Isabelle
collection PubMed
description A methodological study devoted to the Mannich-like multicomponent synthesis of the antiplatelet agent (±)-clopidogrel (7) and the ethyl ester analogue 6 is described. The process involves the formation of 2-chlorophenyl zinc bromide (2) and its subsequent reaction with an alkyl glyoxylate and 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (3). We demonstrate that the organozinc reagent 2 also constitutes a very convenient nucleophile for the multicomponent synthesis of the benzylamine core of ticlopidine (9).
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spelling pubmed-62592002018-12-06 2-Chlorophenyl Zinc Bromide: A Convenient Nucleophile for the Mannich-Related Multicomponent Synthesis of Clopidogrel and Ticlopidine Aillaud, Isabelle Haurena, Caroline Gall, Erwan Le Martens, Thierry Ricci, Gino Molecules Article A methodological study devoted to the Mannich-like multicomponent synthesis of the antiplatelet agent (±)-clopidogrel (7) and the ethyl ester analogue 6 is described. The process involves the formation of 2-chlorophenyl zinc bromide (2) and its subsequent reaction with an alkyl glyoxylate and 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (3). We demonstrate that the organozinc reagent 2 also constitutes a very convenient nucleophile for the multicomponent synthesis of the benzylamine core of ticlopidine (9). MDPI 2010-11-11 /pmc/articles/PMC6259200/ /pubmed/21072025 http://dx.doi.org/10.3390/molecules15118144 Text en © 2010 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 license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Aillaud, Isabelle
Haurena, Caroline
Gall, Erwan Le
Martens, Thierry
Ricci, Gino
2-Chlorophenyl Zinc Bromide: A Convenient Nucleophile for the Mannich-Related Multicomponent Synthesis of Clopidogrel and Ticlopidine
title 2-Chlorophenyl Zinc Bromide: A Convenient Nucleophile for the Mannich-Related Multicomponent Synthesis of Clopidogrel and Ticlopidine
title_full 2-Chlorophenyl Zinc Bromide: A Convenient Nucleophile for the Mannich-Related Multicomponent Synthesis of Clopidogrel and Ticlopidine
title_fullStr 2-Chlorophenyl Zinc Bromide: A Convenient Nucleophile for the Mannich-Related Multicomponent Synthesis of Clopidogrel and Ticlopidine
title_full_unstemmed 2-Chlorophenyl Zinc Bromide: A Convenient Nucleophile for the Mannich-Related Multicomponent Synthesis of Clopidogrel and Ticlopidine
title_short 2-Chlorophenyl Zinc Bromide: A Convenient Nucleophile for the Mannich-Related Multicomponent Synthesis of Clopidogrel and Ticlopidine
title_sort 2-chlorophenyl zinc bromide: a convenient nucleophile for the mannich-related multicomponent synthesis of clopidogrel and ticlopidine
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259200/
https://www.ncbi.nlm.nih.gov/pubmed/21072025
http://dx.doi.org/10.3390/molecules15118144
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