مشخصات پژوهش

Electrochemistry provides a versatile means for the selective reduction and oxidation of organic compounds. The importance of an electrochemical synthesis lies not only in the selectivity of the reaction, but also in the formation of electrons at the electrode surface [1]. Since the electrons are reagent free, pollution of the environment by spent reagents can be avoided. Recently, we have dealt with the electrochemical oxidation of 3,4-Dihydroxycinnamic acid (1) in aqueous solution [2,3]. Our previous studies show that the electrochemically generated p-quinone imine is a reactive intermediate and as a Michael acceptor, participates in different types of reactions [2-4]. On the other hand barbituric acid derivatives are well known to possess antibacterial, sedatives, herbicides, fungicides and antiviral agents [5,6]. However, until now, no report has been published about the electrooxidation of 3,4-Dihydroxycinnamic acid (1) in the presence of barbituric acid derivatives. In this work electrochemical oxidation of 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone (1) has been studied in the presence of 2-Mercapto benzimidazole (3a) 2-Mercapto-5-methoxybenzimidazole (3b) and 2-Mercapto-5-methylbenzimidazole (3c) as nucleophiles (Fig. 1). Fig. 1. Some electrochemical techniques such as: cyclic voltammetry using diagnostic criteria derived by Nicholson and Shain for various electrode mechanisms and controlled-potential coulometry were used. Our results indicate the participation of electrochemically generated o-quinone imine in Michael-type addition reaction with 2-Mercapto benzimidazole derivatives (3a–c) to form the corresponding cinnamic acid derivatives.