Abstarct: Of the more than 20 million chemical compounds currently registered, about one half contains heterocyclic systems. In this research work, new derivatives of 3-aryl-substituted-6-chloroimidazo[2,1-a] phthalazines synthesized by the Sonogashira coupling reaction from 1,4-dichlorophthalazine, propargyl amine, and aryl halides. Also in the continue, new derivatives of mono and bis 1,2,3-triazole-lixnked phthalazine-1,4-dione synthesized from 2-methyl-2,3-dihydrophthalazine-1,4-dione and 2,3-dihydrophthalazine-1,4-dione, propargyl bromide, and aromatic azides in the presence of copper catalyst via copper-catalyzed click reactions. The structures of all the synthesized compounds were confirmed by the spectroscopic data. A number of synthesized compounds were evaluated for anti-bacterial activities.