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Title Synthesis of the N,N-Dimethyl-1,3-benzothiazole-2-sulfonamide Based on the Electrochemical Oxidation of 2-Mercaptobenzoxazole in the Presence of the Diethylamine
Type Presentation
Keywords N,N-Dimethyl-1,3-benzothiazole-2-sulfonamide 2-Mercaptobenzoxazole Diethylamine
Abstract The organosulfur compounds play a very important role in various fields such as organic synthesis, materials science, agriculture, and medicinal chemistry. In particular, sulfonamide derivatives exhibit a wide range of biological activities such as anticancer, antibacterial, anticonvulsant, anti-inflammatory, and antiviral and HIV protease inhibitory activity [1]. Thus, synthesis of biologically and synthetically important sulfur-nitrogen bonds is one of the essential transformations in organic synthesis. However, the limited availability of commercial starting materials, the formation of undesired by-products and/or harsh reaction conditions are the main drawbacks of these methods. Therefore, the search for novel and ecofriendly approaches to the synthesis of sulfur-nitrogen bond-containing compounds is a challenge and open discussion. Along with this line, recently, oxidative coupling of thiols and N–H compounds has gained a lot of attention because of the eye-catching and promising properties [2]. To the best of our knowledge, the presented synthetic methods for the production of sulfonamide compounds still suffer from drawbacks so long-time conditions, un-safe and multi-step methods, high temperatures, using of organic and toxic solvents, and the employing of the expensive catalysts and toxic transition metals. With this in mind, we have developed a mild electrochemical procedure for the synthesis of a sulfonamide compound by employing of the 2-Mercaptobenzoxazole in the presence of the diethylamine, as a metalfree and catalyst-free procedure in room temperature and aqueous solution. As the first step, the exhaustively voltammetric survey as an easy-to-apply electrochemical technique has done in more details in order to shed more lights on the mechanistic aspect of this green electrochemical transformation under various conditions. The pH-dependence, scan rate effect, various solvents, and diagnostic tests have evaluated to obtain better insight into this reacti
Researchers Davood Nematollahi (Third Researcher), (Second Researcher), (First Researcher)