9-α-Nitro(hydroxy, amino)benzylidene- and 9-Hydroxy(amino)methylene-4-azafluorenes

Nitration of 9-benzylidene-4-azafluorene with acetyl nitrate leads to the formation of its 9-α-nitrobenzylidene derivative; reduction of the latter gives the corresponding enamine and oxime. Reaction of 4-azafluorene with ethyl benzoate and ethyl formate gives the hydroxybenzylidene and hydroxymethylene derivatives, which upon condensation with amines generate the corresponding enamines. Reduction of 9-formylazafluorene oxime gives 9-aminomethyleneazafluorene. All of the newly synthesized compounds were isolated in the form of mixtures of their Z- and E-isomers, and their structures were established using PMR spectroscopy. © 1991 Plenum Publishing Corporation.