The multi-component reaction of diacetyl triazole derivative with ethyl cyanoacetate and various aromatic aldehydes according to the conventional and solvent free methods leads to the corresponding 2-oxonicotinonitriles. A number of chalcones has been obtained via condensation of diacetyl triazole derivative with a variety of aromatic aldehydes. Heterocyclization of dichalcones with thiourea, hydroxyl amine, 3-aminocrotononitrile and hydrazine hydrate leads to a series of functionalized triazoles. Fluorescent properties of some products have been studied and characterized by λem.max 463–499 nm. A series of newly synthesized compounds demonstrate high antimicrobial activity against the tested microorganisms