2-(5-(Naphthalenyloxymethyl)-2-thioxo-1,3,4-oxadiazol-3(2H)-yl)aceto hydrazide (1) undergoes facile condensation with aromatic aldehydes to afford the corresponding N'-aryl-2-(5-(naphthalenyloxymethyl)-2-thioxo-1,3,4- oxadiazol-3(2H)-yl)acetohydrazide (2a-e) in good yields. Cyclocondensation of compounds (2a-e) with thioglycolic acid yields N-(2-aryl-4-oxothiazolidin-3-yl)-2-(5-(naphthalenyloxymethyl)-2-thioxo-1,3,4-oxadiazol-3(2H)-yl) acetamide (3a-e). The structures of these compounds were established on the basis of analytical and spectral data. All the newly synthesized compounds were evaluated for their antibacterial and antifungal activities.