Synthesis, Characterization and Anti-corrosion Activity of New Triazole, Thiadiazole and Thiazole Derivatives Containing Imidazo[1,2-a]pyrimidine Moiety

Abstract

In this research, several heterocyclic rings (triazole, thiadiazol, thiazol) containing imidazo (1,2-a) pyrimidine moiety have been prepared via a series of reactions. To do this, synthesis of 2-substituted imidazo (1,2-a) pyrimidine was performed by condensation of 2-aminopyrimidine with (4-bromo phenacyl bromide) or (4-phenyl phenacyl bromide). Carbaldehyde group was prepared at position-3 of 2-substituted imidazo/pyrimidine rings by Vilsmeier-Haak reaction. Thiosemicarbazon derivatives (Schiff bases) were synthesized by condensation of 3-carbaldehyde derivatives with thiosemicarbazide. Cyclization of thiosemicarbazone derivatives with Ac2O, 4-bromophenacyl bromide and HCl afforded the corresponding thiadiazole(diacetyl) derivatives, 1,3-thiazole derivatives and 1,2,4-triazole derivatives respectively. Structures of the new derivatives were confirmed via FT-IR spectroscopy, some of which were confirmed via 1H-NMR spectroscopy. Three of these new derivatives were evaluated by their anti-corrosion activity.