This study includes the synthesis of a few different coumarin-3-carboxylic acid derivatives of 1,2,3-triazole and triazoline as a starting material. The first step involves the formation of compound (a) in absolute ethanol through the reaction of coumarin-3-carboxylic acid to thiosemicarbazide. Then compound (a) reacts with chloroacetyl chloride in the presence of triethylamine for compound forming (b). Azide derivative compound (c) was prepared with sodium azide in DMF by compound reaction (b). The heterocyclic compounds 1,2,3-triazole and triazoline derivatives (Mch1, Mch2, d, e , and f) were prepared with some unsaturated compounds such as propergyl bromide, cinnamic acid, and maleic anhydride in DMF from the reaction of compound (c). All compounds were identified by FT-IR, 1H-NMR spectrum, and C.H.N.S elemental analysis. The heterocyclic compounds were tested as an antibacterial activity with certain microorganism types. They showed good antimicrobial activity towards the investigated specific microorganisms.