Benzodiazepines are used as anxiolytic, hypnotic, sedative, and antidepressant drugs and to treat anxiety, insomnia, and epileptic seizures and show other types of biological activities. In this study, ten new 4(2)-(8-hydroxyquinolinil-5)-2(-4)-aryl-2,3-dihydro-1H-1,5-benzodiazepines and their rearrangement products, 2-substituted benzimidazoles, were synthesized from 1-aryl-3- (8-hydroxyquinolinil-5) propenone-1 (-3) and ophenylenediamine in methanol-triethylamine (1:1) solution. The reaction between the diamine and chalcones containing the 8-hydroxyquinoline fragment was carried out under mild conditions by base-catalysis amination of the β-enonic fragment of the chalcones followed by cyclo condensation. The structures of these compounds were studied by spectroscopic methods (IR and 1H-NMR) and their chelating properties were demonstrated. We calculated and discuss their theoretical biological activity and the influence of metal chelation on the electron acceptor hydroxyquinolinic fragment on the electronic spectra.