A series of 2-(arylidene)-indan-1, 3-diones 1 were prepared by Knoevenagel reaction between indane-1,3-dione and the appropriate araldehydes. The alpha,beta-enones 1 have been used as a component of Michael addition with equimolar amounts of 2-aminopyridine/2-aminopyrimidine to give novel heterocyclic systems 4 and 5, respectively. They are reported here for the first time. The structures of the newly synthesized compounds were confirmed by IR, (1)H-NMR, (13)C-NMR, and elemental analysis. All compounds were screened for their antibacterial and antifungal activities. Some of them showed promising activities.