Electrochemical reduction of quinoxalino[2,3-b]quinoxaline

The electrochemical reduction of quinoxalino[2,3-b]quinoxaline gives fluoflavine (2) the structure of which is discussed. The electrochemical reduction of fluoflavine in acidic medium leads to a hexahydroquinoxalino[2,3-b]quinoxaline. A reduction mechanism is proposed based on cyclic voltammetry results and preparative electrolysis. The results obtained in the case of quinoxalino[2,3-b]quinoxaline are used to rationalize the results obtained in the case of pyrazino[2,3-b]pyrazines and pyrazino[2,3-b]quinoxalines.