Synthesis and physical properties of azapolycyclic hydrocarbons. Part 1. Preparation of 1-azabenzanthrone and its condensation products and their structural determination

Abstract

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]phe-nanthro[1,10,9-cde]pentaphene (4), 5,17-diazadibenzo[a,rst]naphtho[8,1,2-cde]pentaphene (3), and 5,10-diazabenzo[rst]phenaleno[1,2,3-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[1,2,3-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 (10) are new structural isomers of fused nanocyclic compounds whose parent aromatic hydrocarbons have not been prepared, though (10) has not actually been isolated.