Synthesis, characterization, and thermal decomposition performance of 1,2,3-triazolyl-substituted 1,3,5-triazines with carbonyl, ester, and azide functional groups

Abstract

Based on the organocatalytic reaction of enamine azide addition of 2,4,6-triazido-1,3,5-triazine to acetylacetone acetoacetic ester, we synthesized a series of previously unknown mono-, di-, and tri(1,2,3-triazolyl)-substituted-1,3,5-triazines that additionally carried carbonyl, ester, and azide groups. The structure of the obtained compounds was proved by NMR (¹H, ¹³C) and IR spectroscopy, and the composition was confirmed by elemental analysis. With the aid of differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) coupled to mass spectrometry (TG-MS), we obtained data on the thermal behavior and decomposition mechanism for these compounds. We demonstrated that di(1,2,3-triazolyl)-substituted 1,3,5-triazines have an increased thermal stability and have higher values of decomposition onset temperature (220–250 °C) in comparison with tri(1,2,3-triazolyl)-substituted 1,3,5-triazines (180 °C and 160 °C, respectively).