SYNTHESIS OF 4-AMINO-SUBSTITUTED-6-HYDROXY AND 11-HYDROXY-NAPHTHO[2,3-G]QUINOLINE-5,12-DIONES, AND THE UNEXPECTED FORMATION OF DISUBSTITUTED IMIDAZO[4,5,1-I,J]NAPHTHO[2,3-G]QUINOLIN-7-ONES

4-Chloroquinoline-5,8-dione (8a) and 6-bromo-4-chloroquinoline-5,8-dione (8b) were reacted with homophthalic anhydride to give tetracyclic compounds 10 and 11 respectively. The 6,11-dihydroxy derivative 12 was prepared in low yield by photochemical addition of benzocyclobutenedione to 4-chloroquinoline-5,8-dione (8a) and in better yield through a Friedel-Crafts reaction of phthalic anhydride with 4-chloro-5,8-dimethoxyquinoline (7a). Whereas 4-chloro-6-hydroxynaphtho[2,3-g]quinoline-5,12-dione (11) was substituted by amines in the usual way to the corresponding 4-amino-substituted derivatives, 4-chloro-11-hydroxynaphtho[2,3-g]quinoline-5,12-dione (10) led to a mixture of 4-amino derivatives and the unexpected 2,6-disubstituted-imidazo[4,5,1-i,j]naphtho[2,3-g]quinolin-7-ones, 13a-b.