SYNTHESIS OF A NOVEL 1,3,5-TRIAZINE DERIVATIVES AS POTENTIAL INHIBITORS OF TUMOR-ASSOCIATED CARBONIC ANHYDRASE IX

Synthesis of a novel 1,3,5-triazine derivatives, starting from cyanuric chloride, is reported. Target structural motives are involved in the s-triazine skeleton via substitution of chlorine atoms by amino group in various aminobenzensulfonamides, piperazines, amino alcoholes and other amino compounds. It was found that substitution of the chlorine atoms of cyanuric chloride can be carried out as C-N coupling catalyzed by Cu(I) supported on weakly acidic macroporous cation exchanger resin of polyacrylate type via the oxidative addition - heterolytic addition - reductive elimination processes. The reaction could proceed as a one-pot/ one-step synthetic process that is carried out under temperature control. Higher and excellent yields with shorter reaction times in comparison with similar usual syntheses realized step by step were obtained. Synthetic procedures optimized by this way can be applied in the preparation of the further various s-triazine with respect to the chemical behaviour of the individual nucleophilic reagents.