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.

Das Naphthalinsulfonat (I) wird mit Chlorsulfonsäure in das Sulfochlorid (II) umgewandelt, aus dem durch Nitrierung, Umsetzung mit β‐Chlorethylamin und Hydrolyse das Nitronaphthylamin (VI) erhalten wird.

Syntheses of 7H-Pyrido-and 7H-Pyrano[2,3,4-kl]acridin-2(3H)-ones from 9-Chloroacridines. -Methods for the peri-annulation of a pyridine or pyran ring to an acridine skeleton are developed. -(GORELIK*, M. V.; TITOVA, S. P.; GORDIEVSKAYA, E. V.; Russ. Chem. Bull. 55 (2006) 9, 1664-1669; State Res.