New 6-substituted-5,6-dihydrobenzo[4,5] imidazo[1,2-c] quinazoline compounds were synthesized using two different protocols: microwave-enhanced and classical heating methods. A comparison study that was set up to compare both the methods and the results showed that the microwave-assisted method produced a better percentage yield (up to 98%) in a very short reaction time (only a few minutes). All compounds were characterized by spectroscopic and elemental analysis. Only one compound was analyzed by single crystal X-ray diffraction despite the difficulties of getting good crystal even after several attempts. The X-ray crystallography results were chemically acceptable and confirmed the structure of benzimidazoquinazoline 5. Incidentally, the studied derivatives were found to emit a very nice blue light when exposed to UV-light. Therefore, a photoluminescence study was performed as a part of the characterization processes. Biological application as an antimicrobial and an antioxidant for the target analogues was performed. Some derivatives exhibited high antibacterial activity against studied Gram-positive strains, although they were not active against Gram-negative strains. Moreover, some of them showed excellent antioxidant activities against both of the studied antioxidant DPPH center dot and ABTS(center dot)(+) radicals. (C) 2019 Elsevier B.V. All rights reserved.