Electrogeneration of nitranion species from nitrofuryl substituted 1,4-dihydropyridine derivatives

Abstract

We have synthesized and studied the electroreduction of 1,4-dihydropyridine derivatives with a nitrofuryl substituent at 4-position. The one-electron reduction of these compounds in non-aqueous medium generates the corresponding nitro radical anion. In addition, the existence of an acidic proton on the 1,4-dihydropyridine ring triggered the appearance of father-son type reactions between the nitro radical anion and the parent compound, generating the corresponding nitranion. The corresponding nitranion was exhaustively generated by controlled potential electrolysis. The nitranion voWe have synthesized and studied the electroreduction of 1,4-dihydropyridine derivatives with a nitrofuryl substituent at 4-position. The one-electron reduction of these compounds in non-aqueous medium generates the corresponding nitro radical anion. In addition, the existence of an acidic proton on the 1,4-dihydropyridine ring triggered the appearance of father-son type reactions between the nitro radical anion and the parent compound, generating the corresponding nitranion. The corresponding nitranion was exhaustively generated by controlled potential electrolysis. The nitranion voltammetric detection permitted a clear separation from the corresponding parent compound.