Hydrogenation and halogenation of 6-phenyl-5-azabenzo[f]fluoranthene and reduction of its adducts with acrylonitrile

The hydrogenation of 6-phenyl-5-azabenzo[f]fluoranthene in the presence of rhenium heptasulfide takes place in the meso positions of its azaanthracene fragment. The reaction of 5-azabenzo[f]fluoranthene with acid chlorides and aluminum chloride in nitrobenzene gives its 8-chloro derivative. The reduction of the adducts of the diene synthesis of 6-phenyl-5-azabenzo[f]fluoranthene with acrylonitrile by means of sodium in butyl alcohol leads to the corresponding aminomethyl derivatives and a product of retrodiene synthesis, viz., the starting azabenzofluoranthene. The reduction of the adduct of the diene synthesis of 1,3-diphenyl-2-azaanthracene with acrylonitrile proceeds similarly. © 1982 Plenum Publishing Corporation.