A Mild Synthesis of o-Ureidobenzonitrile Derivatives via Iodide-Mediated Electrolysis from 2-Aminobenzamides

Abstract

An efficient electrochemical synthesis of o-ureidobenzonitrile derivatives from 2-aminobenzamides and isothiocyanates was developed using ammonium iodide as the electrolyte and mediator (0.5 equivalent). This iodide-mediated desulfurization-cyclization process proceeds under mild conditions in an undivided cell with graphite electrodes, delivering a broad range of products in good to excellent yields (44 examples, up to 98%). This method avoids the use of stoichiometric amounts of strong oxidants and toxic solvents, offering a greener alternative to traditional approaches. The synthesized compounds were evaluated for α-glucosidase inhibition and antioxidant activity, demonstrating moderate biological efficacy, highlighting their potential for pharmaceutical applications.