JOURNAL OF HETEROCYCLIC CHEMISTRY, vol.58, no.10, pp.1943-1954, 2021 (SCI-Expanded)
Coumarin derivatives, one of the organic fluorescent materials, are widely applied in many areas such as laser dyes, organic light emitting diodes (OLED), pharmaceuticals and bio/chemosensors, with the advantages of the large conjugated system and planar structure. In the coumarin analogs, which are polarity sensitive fluorophores, a shift to the red zone is observed in the case of pi expansion at 3-positions and electron donor groups at 7-positions. The present article reports the synthesis of novel hybrid compounds (CD1-CD8) containing coumarin and benzodiazepine rings using ethyl 3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-oxopropanoate reagent and 1,2-diaminobenzene derivatives under optimized reaction conditions with PTSA catalyst. The structures of target compounds synthesized were characterized by FTIR, (HNMR)-H-1, (CNMR)-C-13, HRMS and UV-Vis spectra. The effects of electron withdrawing and electron donor groups in the cyclocondensation reaction that takes place as regioselective were evaluated in detail. The substituent effects were investigated for n-pi* and pi-pi* electronic transitions in UV-Vis Spectroscopy.