A novel series of eleven novel 4-(2, 3-dihydro-4H-1,4-benzoxazin-4-yl)-3-fluoroaniline derivatives (I e – I o) have been synthesized from commercially available 2-aminophenol as a starting material. High yield and high purity indicates lack of side reaction and by product. The chemical structures of the synthesized compounds were confirmed by means of 1HNMR and mass spectral data. The synthesized compounds were then examined for their antibacterial and antifungal activities. Some of them were found to possess good antibacterial and antifungal activity.