This study demonstrated the synthesis and characterization of novel heterocyclic compounds, particularly oxazepine derivatives, using a cycloaddition procedure. The synthesis involved the reaction of chloroacetohydrazide with various aromatic aldehydes under acidic conditions in ethanol solvent to produce hydrazone compounds. These hydrazones subsequently underwent pericyclic synthesis with phthalic anhydride to yield oxazepine derivatives. The physicochemical properties of the synthesized compounds (F1 to F13) were characterized using FT-IR and H-NMR spectroscopy. The antibacterial activity of the synthesized oxazepine derivatives (F8, F9, F10, F11, F12, and F13) was evaluated against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacterial strains using the cup plate agar diffusion technique. Notably, compounds F8, F9, and F10 exhibited potent antibacterial activity against both Gram-positive and Gram-negative bacteria, suggesting their potential as effective antibacterial agents. Molecular docking studies were also conducted to investigate the binding interactions of selected compounds with bacterial protein receptors, specifically Escherichia coli K-12 (PDB ID: 4QGS) and Staphylococcus aureus (PDB ID: 7PQ1). The results demonstrate the potential of these novel oxazepine derivatives as antibacterial agents, highlighting their promising biological activities and molecular interactions with bacterial proteins.