A convenient synthesis of alkyl-2-(2-imino-4-oxothiazolidin-5-ylidene)acetate derivatives involving an electrogenerated base of acetonitrile |
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| Authors: | Najoua Sbei Monia Chebbi Youssef Ben Smida Youssef Arfaoui Khaled Boujlel |
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| Affiliation: | 1. Department of Chemistry, Faculty of Sciences, Laboratory of Analytic Chemistry and Electrochemistry, University of Tunis, El Manar, Tunisia;2. Department of Chemistry, Faculty of Sciences, Laboratory of Physical Chemistry of Condensed Materials, University of Tunis, El Manar, Tunisia;3. Department of Chemistry, Faculty of Sciences, Laboratory of Physical Chemistry of Condensed Materials, University of Tunis, El Manar, Tunisia;4. Laboratory of Physical Chemistry of Microstructures and Micro-systems, University of Cartage, Institut Préparatoire aux Etudes Scientifiques et Techniques, La Marsa, Tunisia |
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| Abstract: | We report a simple method for the synthesis of alkyl-2-(2-imino-4-oxothiazolidin-5-ylidene) acetate derivatives 3 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 derivatives 1 and dialkyl acetylene dicarboxylate 2. The expected products, 3/4, and the structure obtained from X-ray diffraction confirm that the main products are the five-membered heterocycles 3. Furthermore, a mechanism, to explain the reaction pathways, is proposed based on the thermodynamic and kinetic data obtained from quantum calculations. |
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| Keywords: | Alkyl-2-(2-imino-4-oxothiazolidin-5-ylidene) acetates thioureas EGBs X-ray DFT calculation |
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