Tetracycle Formation from the Reaction of Acetophenones with 1-Aminoanthraquinone, and Further Annulation of Pyridine and Diazepine Rings

Abstract

Acetophenones (H, o-, m-, p-Cl, o-aza) react with aminoanthraquinone in pyridine containing solid sodium hydroxide to form 6-(arylcarbonyl)methyl-2-aryl-7H-naphtho[1,2,3-de]quinolin-7-ones (with the 4-(arylcarbonyl)methyl isomer as minor product). Preformed 7H-benzo[e]perimidin-7-one with acetophenone underwent the second part of this process, i.e. nucleophilic substitution to form 6-phenacyl-7H-benzo-[e]perimidin-7-one. Further reactions are described, including cyclization with ammonium acetate/acetic acid to 2,7-diphenyl-1,6-diazabenzo[e]pyrene and 7-phenyl-1,3,8-triazabenzo[e]pyrene, respectively, and with hydrazine hydrate to 3,8-diphenyl-4H-[1,2]diazepino[3,4-4′,3′ : 4,5-f]naphtho[1,2,3-de]quinoline and 3-phenyl-4H-benzo[e][1,2]diazepino[3,4,5-gh]perimidine.