Synthesis of azidopropargylamino-substituted 1,3,5-triazines – novel monomers for the production of energetic polymers

Efficient methods for the synthesis of novel azidopropargylamino-substituted 1,3,5-triazines were developed. 4,6-Diazido-N-(prop-2-yn-1-yl)-1,3,5-triazin-2-amine was obtained by the method of sequential nucleophilic substitution of chlorine atoms in cyanuric chloride by amino and azido groups or by the method of selective substitution of the azido group in triazidotriazine with propargylamine. 6-Azido-N2,N4-dimethyl-N2,N4-di(prop-2-yn-1-yl)-1,3,5-triazine-2,4-diamine was obtained by nitrosation of the corresponding 6-hydrazinyl-N2,N4-dimethyl-N2,N4-di(prop-2-yn-1-yl)-1,3,5-triazine-2,4-diamine. Monomers with a lower melting point were obtained by N-methylation of azidopropargylamino-substituted 1,3,5-triazines.