This article describes the controlled synthesis and characterization of azo oxazolone scaffold compounds
containing multifunctional groups such as carbonyl group, imine and carbon-carbon double bond. The
reaction of the azo-oxazolone with aromatic amines led to the ring-opening of the azo-oxazolone into the corresponding
azo-benzamide derivatives in a short time (average 10 min), resulting in high yield (>90%). All newly
synthesized compounds were characterized by the common spectral analysis such as UV, IR, 1H-NMR, 13CNMR,
Elemental analysis and MS spectrometry.
Objective: The aim of the study was to synthesize new bioactive azo-benzamides by using azo-oxazolone as a
synthon utilizing its ring-opening function.
Materials and Methods: Azo-benzamide derivatives were prepared in very good yield via ring-opening reaction
of azo-oxazolone with aromatic amines in the presence of acetic acid under reflux for few minutes.
Results and Discussion: Chemical structures of the newly synthesized compounds were characterized by UV,
IR, 1H-NMR, 13C-NMR, Elemental analysis and MS spectrometry.
Conclusion: The new azo-oxazolone 4 and azo-benzamide compounds 5a, 5c, 5f, 5h, 5j were screened against
Escherichia coli as G(-ve) and Staphylococcus aureus as G(+ve) using ciprofloxacin as a standard. All compounds
showed high inhibition potency against E-Coli but low inhibition for S-aureus. Compounds 4, 5c, and 5J
showed more reactivity against E-coli.
Others: Also, the compounds were tested for their anti-oxidant activity by both DPPH and FRAP methods. The
results showed that some compounds possessed moderate anti-oxidant activity in comparison to ascorbic acid as
control, typically the compounds bearing OCH3 and OCH2CH3 groups.