Electrochemical behaviour of imipramine in the presence of benzensulfinic acid at glassy carbon electrode

Electrochemical methods are widely used for the study of electroactive compounds in pharmaceutical forms and physiological fluids due to their simple, rapid, and economical properties [1]. Among the popular electrochemical techniques cyclic voltammetry (CV) is the most versatile available ones. Under favorable circumstances, CV can also be used for mechanistic studies of systems in which the electron transfer reactions are coupled to chemical reactions, due to the characteristic appearance of cyclic voltammograms associated with different mechanisms [2]. Tricyclic antidepressant drugs (TCAs) are one of the largest groups of drugs for the treatment of psychiatric disorders such as depression. On the other hand, arylsulfinic acids are widely used in the practice of medicinal chemistry, chemical industry, chemical synthesis. The importance of these compounds has motivated us to synthesize new imipramine derivatives via electrochemical oxidation of imipramine in the presence of arylsulfinic acids. The electrochemical oxidation of imipramine have been studied in a range of pH between 1.0 to 9.0 in the presence of arylsulfinic acids as nucleophiles in aqueous solutions by using cyclic voltammetry and constant current coulometry methods. The results indicate that the dibenzazepine derived from oxidation of imipramine participates in Michael type addition reaction with arylsulfinic acids to form the corresponding new sulfone derivatives of imipramine. The present work has led to the development of a facile and environmentally friendly reagent-less electrochemical method for the synthesis of some new imipramine derivatives in aqueous solutions with high atom economy, under green conditions.