4-(1H-naphtho[1,8-de][1,2,3]triazin-1-ylsulfonyl)aniline [1] undergoes facile condensation with various aromatic aldehydes to gave 4-(1H-naphtho[1,8-de][1,2,3]triazin-1-ylsulfonyl)-N-arylideneaniline [2a-g] in excellent yield. Cyclocondensation of compounds [2a-g] with chloro acetyl chloride yields 1-(4-(1H-naphtho [1,8- de][1,2,3]triazin-1-ylsulfonyl)phenyl)-3-chloro-4-arylazetidin-2-one [3a-g]. The structures of these compounds were established on basis of analytical and spectral data. The newly synthesized compounds were evaluated for their antibacterial and antifungal activities.