Electrochemically induced oxidative cyclization of 2,3-dihydroxypyridine. Synthesis of a novel highly oxygenated heterocyclic compound

摘要

Electrochemical oxidation of 2,3-dihydroxypyridine in aqueous phosphate buffer solution at a glassy carbon electrode has been studied using cyclic voltammetry and controlled potential coulometry. The results indicate that oxidation of 2,3-dihydroxypyridine on glassy carbon electrode shows an irreversible feature in aqueous solution. This data indicates that the electrochemically generated pyridindione is unstable and via an oxidative conversion pathway converts to a novel highly oxygenated heterocyclic compound. By means of the obtained electrochemical data, an efficient, one-pot method for the synthesis of this heterocyclic compound based on the oxidative cyclization of 2,3-dihydroxypyridine under green conditions, and in a good yield and purity is described.