Phenylenediamine reacted readily with 2 mol of ethyl acetoacetate to give diethyl (2Z,2'Z)-3,3'- [(1,4-phenylene)bisimino]dibut-2-enoate, which reacted with dimethylformamide dimethylacetal, activated methylene nitriles, ylidenemalononitriles and phenyl and benzoyl isothiocyanate to give, respectively, a 4,7-phenanthroline-2,9-dicarboxylate-1,10-diol, and tricyclic bispyridine and bispyrimidine derivatives. Two compounds showed strong antibacterial activity against several microorganisms, while six others showed high to moderate activity.