2-(4-Methoxyphenyl)-1-oxo-1,2-dihydro-1,6-naphthyridine-4-carboxamide ( 4c ) underwent Hofmann rearrangement with iodobenzene diacetate in methanol to give the corresponding 4-amino compound ( 6c ). This, when reacted with 2,4-pentanedione and then hot phosphoryl chloride (attempted Combes synthesis) gave a new heterocyclic system, 6-(4-methoxyphenyl)-2-methylpyrido[3,2- c]pyrrolo[2,3- e]azocin-7(6 H)-one ( 9c ). This showed typical pyrrole-type reactivity at the 3-position. Alternatively, an attempt to convert the 4-NH 2 in 6c to 4-OH by diazotization gave, instead, a [1,2,3]triazolo[1,5- a]pyridine-3-carboxaldehyde ( 16c ). The same series of reactions on a benzo analog, 2-methyl-1-oxo-1,2-dihydrobenzo[ b][1,6]naphthyridine-4-carboxamide ( 4a ), gave the same results.