Electrochemical synthesis of new quinone-imines with assisted of 4-ethynylaniline and para-toluidine as nucleophile

Electrochemical oxidation of 3 and 4 substituted catechols in the presence of 4-ethynylaniline and para-toluidine as a nucleophile in acetonitrile/ sodium acetate 0.15 M (30/70) solution has been carried out in detail with employing the cyclic voltammetry and controlled potential coulometry methods. The results show that the obenzoquinones derived from these catechols participate in Michael type reaction with these nucleophiles to form the corresponding new p-quinone imines. We derived some new p-quinone-imines derivatives with good yields based on the electrochemical oxidation in the controlled potential situation, without toxic reagents and solvents, at the carbon electrode, and in an undivided cell.

Automated summary

This study investigates the electrochemical oxidation of 3 and 4 substituted catechols, and finds that the resulting p-quinones can react with nucleophiles to form p-quinone imine derivatives.