Collect. Czech. Chem. Commun. 1990, 55, 1311-1320

Synthesis and antibacterial activity of some 1-aryl-1,4-dihydro-4-oxocinnoline-3-carboxylic acids

Stanislav Rádl, Jaroslav Moural and Radoslava Bendová

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


The coupling reaction of corresponding benzene diazonium chlorides with benzoyl acetates IIIa-IIIc yielded intermediates IVa-IVe. Their intramolecular nucleophilic cyclization provided 1-aryl-1,4-dihydro-4-oxocinnoline-3-carboxylates Va-Ve. Compounds Va, Vb, Vd, and Ve were hydrolyzed to acids VIa-VIc. Treatment of these acids with the respective cyclic amines yielded compounds VIIa-VIIg which were converted to their hydrochlorides. All compounds prepared were tested for their antimicrobial activity in vitro.