2-Aminoquinoline and 3-amino-1, 8-naphthyridine (XI) were cyclized by ethoxy methylenemalonate and both afforded an angular type products (II and XIII). Hydrolysis of II, ethyl 4-hydroxy-5-methyl-1, 6-phenanthroline-3-carboxylate, and XIII gave 2-aminoquinoline from II and carboxylic acid derivatives (III and XIV) from the others. N-Alkylation of III, ethyl carboxylate of III, and XIV gave IV, VII, and XV. The active methylene group in XVI was oxidized with selenium dioxide to the aldehyde derivative (XVII) and XVII was oxidized with hydrogen peroxide to obtain a carboxylic acid derivative (XVIII). Antibacterial test of the synthesized compounds, III to VII, XV to XVIII, and diazaphenanthrenes (XIX to XXXIII) indicated that these compounds have a slightly strong antibacterial activity against Pseudomonas aeruginosa.
