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This study was designed to synthesize, characterize and to evaluate the pharmacological activity of 1, 3-benzoxazin- 4-one derivatives. Totally thirteen compounds, were synthesized by conventional method. Purity of the synthesized compounds was ascertained by TLC and melting point determination by open capillary tube method and they were characterized by IR and NMR spectroscopic methods. Antidepressant activity of all the synthesized compounds was evaluated by despair swim test by using Sprague Dawley Rats. Standard drug Imipramine was used as the control. In the results of the spectral study, all the compounds showed characteristic peak in IR and NMR spectroscopy. In the despair swim test, all the synthesized derivatives showed antidepressant activity. Among them three Compounds (A4, A5 and A7) showed significant antidepressant activity comparing with control drug imipramine. These results are useful for the further investigation in the future.