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

Aimar Gonzalo-Barquero; Bénédicte Lepoittevin; Jacques Rouden; Jérôme Baudoux

doi:10.3390/molecules28217333

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

Molecules. 2023 Oct 30;28(21):7333. doi: 10.3390/molecules28217333.

Authors

Aimar Gonzalo-Barquero¹, Bénédicte Lepoittevin¹, Jacques Rouden¹, Jérôme Baudoux¹

Affiliation

¹ Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507, ENSICAEN, UNICAEN, CNRS, Normandie Université, 6 Bd du Maréchal Juin, 14050 Caen, France.

Abstract

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.

Keywords: dithiocarboxylic acids; dithioesters; grignard reagents; mitsunobu reaction; thioamides.

Grants and funding

This research was funded by the Normandy Region (fellowships to A.G.-B.). The authors acknowledge the Ministery of Higher Education and Research, the LABEX SynOrg (ANR-11-LABX-0029) and the European FEDER.