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. (5th January 2021)

• Record Type: Journal Article
• Authors: Boureghda, Chaima; Boulcina, Raouf; Dorcet, Vincent; Berrée, Fabienne; Carboni, Bertrand; Debache, Abdelmadjid
• Is Part Of: Tetrahedron letters. Volume 62(2021)
• Publication Date: 2021-01-05
• Subjects: Knoevenagel reaction -- 5-Arylidene rhodanine -- 2-Mercaptoacrylic acids -- Sodium sulfite -- Benzoxaborole; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152690
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: 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 Na2 SO3 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.