Facile synthesis of 5-arylidene rhodanine derivatives using Na2SO3 as an eco-friendly catalyst. Access to 2-mercapto-3-aryl-acrylic acids and a benzoxaborole derivative

Chaima Boureghda (1) , Raouf Boulcina (1) , Vincent Dorcet (2) , Fabienne Berree (2) , Bertrand Carboni (2) , Abdelmadjid Debache (1)

1 UMC - Université Frères Mentouri – Constantine 1 = Constantine 1 – Frères Mentouri University
2 ISCR - Institut des Sciences Chimiques de Rennes

A simple, efficient and environment-friendly procedure for the synthesis of 5-arylidene rhodanines derivatives via a Knoevenagel type reaction was developed using rhodanine, a variety of differently substituted aldehydes and Na2SO3 as benign catalyst in ethanol. Selected 5-arylidene rhodanines were subjected to basic hydrolysis to afford 2-mercapto-3-substituted-acrylic acids. The presence of a boronic acid group is well tolerated in such transformations. In the case of 2-formylphenylboronic acid, this sequence opens access to a new benzoxaborole derivative.

Mots clés: Knoevenagel reaction; 5-Arylidene rhodanine; 2-Mercaptoacrylic acids; Sodium sulfite; Benzoxaborole

Domaines: Chimie

Chaima Boureghda, Raouf Boulcina, Vincent Dorcet, Fabienne Berree, Bertrand Carboni, et al.. Facile synthesis of 5-arylidene rhodanine derivatives using Na2SO3 as an eco-friendly catalyst. Access to 2-mercapto-3-aryl-acrylic acids and a benzoxaborole derivative. Tetrahedron Letters, 2021, 62, pp.152690. ⟨10.1016/j.tetlet.2020.152690⟩. ⟨hal-03122490⟩