Abstract 9H-Indeno [2, 1-c] pyridine-1 (2H), 9-dione, prepared by a new efficient route, reacts with 3, 4-dimethoxy-phenyllithium to form the keto alcohol (7), which rearranges with hydrazoic acid to form 5-(3, 4-dimethoxyphenyl) benz [c][2, 7] naphthyridin-4 (3H)-one. The N-oxide photolyses smoothly to yield dehydroperloline as the sole product.