In this research some new derivatives of 1,3-Oxazepine and 1,3-Diazepine with sulfadiazine moiety has been synthesized. At the first we prepared the azo derivatives of O-tolidine [A] by the coupling reaction of the dizaonium slat of sulfadiazine with O-tolidine, then different compounds of Schiff base [B1-B5] were prepared by the reaction of compound [A] with benzaldehyde derivatives. 1,3-oxazepine derivatives [C1-C5] and [C6-C10]were synthesized by the cycloaddition reaction of compounds [B1-B5] with the malic anhydride and phthalic anhydride respectively. In the last step compounds [C1-C10] were converted to diazepene derivative [D1-D10] by reaction with sulfadiazine. All the prepared compounds were characterized by FT-IR spectrophotometer and some of their by mass and 1H-NMR spectrophotometers as well as C, H, N and S analysis. All the reactions were monitored by Thin Layer Chromatography (TLC) and some of physical properties like melting point and retention factor was recorded for the prepared compounds. Finally, Biological activity of some prepared compounds were tested as antibacterial agents for two different types of bacteria Klebsiella pneumonia (Gram-negative) and Streptococcus aureus (Gram positive).