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

Abstract

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.

An Expedient Synthesis of Unusual Oxoisoaporphine and Annelated Quinoline Derivatives

“…2 About the same time, the synthesis of 7H-dibenzo [de,h]quinolin-7-one derivatives via N-phenethylphthalimides was reported in connection with their possible antiviral activity, 3 and the synthesis of some 2,3-dihydro derivatives by cyclization of 3-(b-dialkoxyarylethylamino)phthalides was also reported. 4 In the case of the 5-methoxy-2,3-dihydro analogue (2), this compound was obtained in large enough quantities to subject it to some preliminary reduction studies, affording a basic carbinol whose structure, however, was not adequately confirmed. Since the 1980's, a small group of alkaloids possessing the 7H-dibenzo [de,h]quinoline skeleton and bearing different substitution patterns have been isolated from Menispermum dauricum DC.…”

Convenient Synthesis of 7H-Naphtho-[1,8-gh]quinolin-7-one

“…In addition, ultraviolet (UV)-visible spectra of homologs (1a, 1b, and 1c) resemble each other (Fig. 8), and comparison of the melting points of 1c (168 C) with those of 1a (170 C [15] ) and 1b (181-183 C [4] ) is interesting. Compound 1c showed a melting point very near that of 1a.…”

Interplay of thermochemistry and Structural Chemistry, the journal (volume 17, 2006) and the discipline

“…As alkaloids possessing the 7H-dibenzo[de,h]quinoline skeleton have been earlier synthesized due to their possible photo-and electrochemical properties [268], as intermediates for the formation of dyes [269] and as some of them have exhibited cytotoxic activities against a small panel of cancer cell lines [270]. With the objective to understand the synthesis of some alkaloids in which the number of oxy groups varies Sobarzo-Sánchez, Castedo and De la Fuente [271] in the next paper report the synthesis and theoretical study of 5,6-dimethoxy-2,3-dihydro-7H-dibenzo[de,h] quinolin-7-one.…”