2,2'-(1,3,4-oxadiazole-2,5-diyl)diacetonitrile 2 has been prepared expeditiously from 2-cyano-N'-(2-cyanoacetyl)acetohydrazide1. Reaction of 2,2'-(1,3,4-oxadiazole-2,5-diyl)diacetonitrile 2 with aromatic aldehydes under mild alkaline conditions afforded the corresponding condensation products 3a-d, which in turn allowed to react with hydrazine, phenylhydrazine or hydroxylamine to give pyrazole and iosxazole derivatives (4-6)a-d. Also compound 3a-d was reacted with acetylacetone or ethyl acetoacetate to give pyran derivatives (7,8)a-d. Condensation of compound 2 with cyclopentanone afforded compound 9 which was reacted with acetylacetone or ethyl acetoacetate to give the corresponding spiropyran derivatives 10 and 11 respectively. The one-pot reaction of compound 2 with carbon disulfide or phenylisocyanate and ethyl chloroacetate under phase transfer catalysis conditions afforded the corresponding thiophene derivatives 12 and 13 respectively. Finally, the reaction of compound 2 with ethylcyanoacetate was studied carefully under non-catalytic and catalytic conditions where compounds 14-16 were obtained respectively. The antimicrobial activity of the obtained compounds was examined. The obtained products were characterised by their elemental and spectral data.