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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
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. |
format | Online Article Text |
id | pubmed-10649591 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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