Synthesis and Reactivity of Fluorinated Dithiocarboxylates to Prepare Thioamides—Effective Access to a 4-Styrenylthioamide-Cinchona Alkaloid Monomer

A simple and rapid access to fluorinated dithioesters was developed by a one-pot sequence corresponding to a Grignard reaction—Mitsunobu type substitution. These activated dithioesters have shown excellent reactivity in an aminolysis reaction from simple or more complex primary amines such as cincho...

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Autores principales: Gonzalo-Barquero, Aimar, Lepoittevin, Bénédicte, Rouden, Jacques, Baudoux, Jérôme
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10649591/
https://www.ncbi.nlm.nih.gov/pubmed/37959753
http://dx.doi.org/10.3390/molecules28217333
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author Gonzalo-Barquero, Aimar
Lepoittevin, Bénédicte
Rouden, Jacques
Baudoux, Jérôme
author_facet Gonzalo-Barquero, Aimar
Lepoittevin, Bénédicte
Rouden, Jacques
Baudoux, Jérôme
author_sort Gonzalo-Barquero, Aimar
collection PubMed
description A simple and rapid access to fluorinated dithioesters was developed by a one-pot sequence corresponding to a Grignard reaction—Mitsunobu type substitution. These activated dithioesters have shown excellent reactivity in an aminolysis reaction from simple or more complex primary amines such as cinchona alkaloids. A stoichiometric amount of amine was sufficient to prepare various thioamides, including a 4-styrenylthioamide cinchonidine monomer, under environmentally friendly conditions, at room temperature, and in a very short time.
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spelling pubmed-106495912023-10-30 Synthesis and Reactivity of Fluorinated Dithiocarboxylates to Prepare Thioamides—Effective Access to a 4-Styrenylthioamide-Cinchona Alkaloid Monomer Gonzalo-Barquero, Aimar Lepoittevin, Bénédicte Rouden, Jacques Baudoux, Jérôme Molecules Article A simple and rapid access to fluorinated dithioesters was developed by a one-pot sequence corresponding to a Grignard reaction—Mitsunobu type substitution. These activated dithioesters have shown excellent reactivity in an aminolysis reaction from simple or more complex primary amines such as cinchona alkaloids. A stoichiometric amount of amine was sufficient to prepare various thioamides, including a 4-styrenylthioamide cinchonidine monomer, under environmentally friendly conditions, at room temperature, and in a very short time. MDPI 2023-10-30 /pmc/articles/PMC10649591/ /pubmed/37959753 http://dx.doi.org/10.3390/molecules28217333 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Gonzalo-Barquero, Aimar
Lepoittevin, Bénédicte
Rouden, Jacques
Baudoux, Jérôme
Synthesis and Reactivity of Fluorinated Dithiocarboxylates to Prepare Thioamides—Effective Access to a 4-Styrenylthioamide-Cinchona Alkaloid Monomer
title Synthesis and Reactivity of Fluorinated Dithiocarboxylates to Prepare Thioamides—Effective Access to a 4-Styrenylthioamide-Cinchona Alkaloid Monomer
title_full Synthesis and Reactivity of Fluorinated Dithiocarboxylates to Prepare Thioamides—Effective Access to a 4-Styrenylthioamide-Cinchona Alkaloid Monomer
title_fullStr Synthesis and Reactivity of Fluorinated Dithiocarboxylates to Prepare Thioamides—Effective Access to a 4-Styrenylthioamide-Cinchona Alkaloid Monomer
title_full_unstemmed Synthesis and Reactivity of Fluorinated Dithiocarboxylates to Prepare Thioamides—Effective Access to a 4-Styrenylthioamide-Cinchona Alkaloid Monomer
title_short Synthesis and Reactivity of Fluorinated Dithiocarboxylates to Prepare Thioamides—Effective Access to a 4-Styrenylthioamide-Cinchona Alkaloid Monomer
title_sort synthesis and reactivity of fluorinated dithiocarboxylates to prepare thioamides—effective access to a 4-styrenylthioamide-cinchona alkaloid monomer
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10649591/
https://www.ncbi.nlm.nih.gov/pubmed/37959753
http://dx.doi.org/10.3390/molecules28217333
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