Electrocatalytic multicomponent assembling of aldehydes, dimedone and 1-naphthylamine for synthesis of novel tetrahydrobenzo[c]acridin-8(7H)-one derivatives

An efficient and convenient synthesis of novel tetrahydrobenzo[c]acridin-8(7H)-one derivatives is described using the electrogenerated anion of acetonitriles as the base in the presence of tetrabutylammonium fluoride as an effective supporting electrolyte in a one-pot, three-component condensation of aromatic aldehyde, dimedone and 1-naphthyl amine. The reaction carried out in an undivided cell containing an iron cathode and a graphite anode under a constant current density of 5 mA/cm^2 (I=20 mA, electrode surface=5 cm^2) in CH3CN at room temperature was found to be optimum for the electrochemically induced chain process and resulted in the highest yield.