2-styrylchromones have structural similarities with flavonoids, particularly those belonging to the class of flavones. Three new 2-styrylchromones and their two analogues have been prepared from β–diketones in acidic medium. The structures of all synthesized compounds were confirmed by spectral studies like FT-IR, 1H-NMR, 13C-NMR and Mass Spectroscopy. The antioxidant and antimicrobial activities of synthesized compounds were determined by superoxide free radical (NBT) method and Agar-cup method respectively. Among the five synthesized compounds, 16, 17 show good antioxidant activity whereas 16, 15 show better antimicrobial activity.