1,4,5-TRISUBSTITUTED 1,2,3-TRIAZOLES IN THE SYNTHESIS OF BI- AND POLYCYCLIC COMPOUNDS

At present, nitrogen-containing heteroaromatic compounds have found application due to the wide range of their biological activity. Based on this, it can be assumed that the simultaneous combination in the structure of several azacyclic fragments of different nature can lead to the creation of new compounds that potentially have a variety of physiological effects. In the presented work, on the basis of the cyclocondensation reaction of 5-amino-1-aryl(hetaryl)-1,2,3-triazole-4-carboxamides and heterocyclic alpha-monobromo-substituted ketones with various nucleophiles, bi- and polynuclear heterocyclic compounds were synthesized, combining heterocyclic (potentially pharmacoform) structural fragments of various nature. In particular, the target [1,2,3]-triazole-[4,5-d]-pyrimidinones with high yields; cyclocondensation of 2-bromo-1-(5-methyl-1-phenyl-1,2,3-triazol-4-yl)-ethanone and 2-bromo-1-(5-methyl-1-(1,2,4 -triazol-3-yl)-1,2,3-triazol-4-yl)ethanone with thiourea and its functional derivatives with access to bi- and tricyclic heterocyclic assemblies combining triazole (sim- and vic-) and thiazole fragments at the same time. It was found that in a solution of dimethyl sulfoxide for 4-(5-methyl-1-phenyl-1,2,3-triazol-4-yl)thiazol-2-amine aminoimine tautomerism is fixed, for the nitrogen atom of the thiazole fragment and the amino group there is one common (averaged signal) -215.6 ppm. having a correlation with the proton of the CH=cycle in the region of 7.17 ppm. changes in the H-1, C-13, and N-15 NMR spectra and the dominance of the amine form of the product. Iin the interaction of the above heterocyclic alpha-bromo ketones with such an N-nucleophile as 2-aminopyridine, the corresponding imidazo[1,2-a]pyridines were obtained. The composition and structure of the synthesized compounds were proved by NMR and IR spectroscopy and confirmed by elemental analysis data.