A convenient synthesis of alkyl-2-(2-imino-4-oxothiazolidin-5-ylidene)acetate derivatives involving an electrogenerated base of acetonitrile. (4th March 2017)

• Record Type: Journal Article
• Authors: Sbei, Najoua; Haouas, Baya; Chebbi, Monia; Smida, Youssef Ben; Arfaoui, Youssef; Boujlel, Khaled; Benkhoud, Mohamed Lamine
• Is Part Of: Journal of sulfur chemistry. Volume 38:Number 2(2017)
• Page Start: 152
• Page End: 162
• Publication Date: 2017-03-04
• Subjects: Alkyl-2-(2-imino-4-oxothiazolidin-5-ylidene) acetates -- thioureas -- EGBs -- X-ray -- DFT calculation; Sulfur -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.72305
• DOI: 10.1080/17415993.2016.1259416
• Languages: English
• ISSNs: 1741-5993

Abstract

ABSTRACT: We report a simple method for the synthesis of alkyl-2-(2-imino-4-oxothiazolidin-5-ylidene) acetate derivatives3 in good yields under mild conditions. The electrogenerated cyanomethyl base (EGB), obtained from electroreduction of acetonitrile-0.1 M TBABF4, assists the reaction between thiourea derivatives1 and dialkyl acetylene dicarboxylate2 . The expected products, 3 /4, and the structure obtained from X-ray diffraction confirm that the main products are the five-membered heterocycles3 . Furthermore, a mechanism, to explain the reaction pathways, is proposed based on the thermodynamic and kinetic data obtained from quantum calculations. GRAPHICAL ABSTRACT: