Triazido-s-triazin

Azide ion is a rather weak nitrogen nucleophile, but in aqueous acetone (20°, 5 min) it readily produces 2-azido-4,6-dichloro-s-triazine (330) and also yields more slowly (0°, 12 hr, 90% yield) the 2,4,6-triazido-s-triazine. The latter is rapidly hydrolyzed (50°) to cyanuric acid and is easily mono-aminated (0°, 1 hr, in ether). 

No tetrazolo species were found in solutions of 2,4,6-triazido-s-triazine and 2,4,6-triazidopyrimidine (79UKZ975). 

T. Sato, A. Narazaki, Y. Kawaguchi, H. Niino, G. Bucher, Dicyanocarbodiimide and Trinitreno-s-triazine Generated by Consecutive Photolysis of Triazido-s-triazine in a Low-Temperature Nitrogen Matrix, Angew. Chem. Int. Ed., 2003, 42, 5206-5209. 

The synthesis, characterization, and energetic properties of various heterocycles containing azide groups are reported. Compound 105 is prepared by the reaction of cyanuric chloride with sodium azide. The preparation of 106 utilizes the conversion of a pyrazole derivative by reaction with hydrazine to form the hydrazo intermediate which is subsequently reacted with NaN02. 2,5,8-Trichloro-s-heptazine is converted quantitatively into 2,5,8-triazido-s-heptazine (107) with trimethylsilyl azide. The nucleophilic reaction of hydrazine with 4,4, 6,6 -tetra(chloro)hydrazo-l,3,5-triazine... 

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