I Hyakunincho, Shinjuku-ku, Tokyo 160, Japan Preparation of 1 -azabenz[de]anthrone (27) was carried out by making use of a German Patent reaction. An improved procedure gave (27) easily and rapidly. Compound (27) underwent self-condensation via a zinc-catalysed method or an alkali-fusion procedure. The zinc-catalysed condensation product was separated into four isomers; 3,12-diazatetrabenzo[a,cd,j,lm]perylene ( 7 ) , 3,15-diazabenzo[rst]phenanthro[l,l O,9-cdelpentaphene (4), 5,17-diazadibenzo[a,rst] naphtho[8,1,2-cde] pentaphene (3), and 5,1O-diazabenzo[rst]phenaleno[l,2,3-de]pentaphene (6). The major component was (3). The reduced product after alkali-fusion condensation of (27) was separated into four isomers; ( 7 ) , (3), (6), and 5,14-diazadinaphtho[l,2,3-cd: 1 ',2',3'-lm]perylene ( 2 ) . The major component was ( 2 ) .The structures of the isomers were assigned from their oxidation products, m.p., u.v.-visible, i.r., and mass spectra. According to our assignments, (6) and possibly 5,14-diazatetrabenzo-[a,cd,lm,o] perylene (1 0) are new structural isomers of fused nanocyclic compounds whose parent aromatic hydrocarbons have not been prepared, though (10) has not actually been isolated.
