A method for peri annulation of the pyridine or pyran ring to acridine was developed and used to obtain 7H pyrido and 7H pyrano[2,3,4 kl]acridin 2(3H) ones. The peri groups were formed by a reaction of 9 chloro 1 nitroacridine with a CH acid (malononitrile, ethyl cyanoacetate, and ethyl malonate) followed by reduction of the nitro group, or by a reaction of 1 amino 10 methylacridone with PCl 5 and then with a CH acid. Replacement of the chlorine atom in 9 chloro 1 methoxyacridines by the residue of the CH acid with subsequent heating in an acidic medium afforded 7H pyrano[2,3,4 kl]acridin 2(3H) ones, which belong to a novel heterocyclic system.

1 Acylamino 10 methylacridones in a polar aprotic solvent underwent base catalyzed cy clization into the corresponding 7 methyl 7H pyrido[2,3,4 kl]acridin 2(3H ) ones. Heating of 1 butylaminoacridone in acetic anhydride in the presence of p toluenesulfonic acid and potassium acetate afforded 3 butyl 7H pyrido[2,3,4 kl]acridin 2(3H ) one, while heating of 1 aminoacridone under the same conditions gave 9 acetoxy 1 acetylimino 1,10 dihydroxy acridine.

9-Chloro-l,10-anthraquinone l-dichlorophosphorylimine formed in the reaction of I-amino-9,10-anthraquinone with PCI 5 followed by dehydrochlorination reacts with primary amines with substitution of chlorine atoms. In the case of aliphatie amines, the reaction occurs further concurrently in two directions: the addition of the amine molecule with the formation of 9,9-di(alkylamino) derivatives of the anthrone and the substitution of hydrogen atom at position 4 with the formation of 4,9-di(alkylamino) derivatives of 1,10-anthraquinone 1 Amine. In the case of aromatic amines, l-amino-9,10-anthraquinone 9-arylimines are the end products. Reactions with the anions of CH-acids containing an alkoxycarbonyl or cyano group occur with substitution in position 9 followed by intramolecular cyclization with the formation of 2-alkoxy-or 2-amino-7H-dibenzo[f,/j]isoquinolin-7-one derivatives, respectively.

Chlorierungen des Dihydroxyanthrachinons (I) mit SOCI, in Gegenwart von Basen wie Triethylamin oder DMF liefern bei hydrolytischer Aufarbeitung der Primärprodukte komplexe Gemische der Anthrachinone (II)‐(IV).