Mechanistic study of in vitro chemical interaction of trimipramine drug with barbituric derivative after its oxidation: Electrochemical synthesis of new dibenzazepine derivative.

ABSTRACT

Electrochemical oxidation of trimipramine in the absence and presence of 1,3 dimethyl barbituric acid as a nucleophile in aqueous solution has been studied using cyclic voltammetry and controlled-potential coulometry electrolysis. Voltammetric studies of electro-oxidation of trimipramine were realized in a range of pH1.0 to 8.0 in the absence and presence of 1,3 dimethyl barbituric acid. Based on the obtained electrochemical results, dimerization is the main reaction of electro-oxidation of trimipramine in the absence of nucleophile. The voltammetric data indicate that the 1,3 dimethyl barbituric acid participation in Michael addition reaction with the oxidized dimeric form of trimipramine via an ECEC electrochemical mechanisms. On the other hand the results indicate existence of a catalytic (EC') electrochemical mechanism in parallel with ECEC electrochemical mechanism. This method provides a facile and one-pot procedure for the synthesis of new dibenzazepine derivative. Finally, a possible mechanism is proposed for the electrode process, on the basis of the present and previous investigations. The product has been characterized by IR, 1H NMR, 13CNMR and MS methods.