Condensed Tetrazolo-1,3,5-triazines. 2. Alkylation and Nucleophilic Substitution of 5-Trinitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-ones

Abstract

ray diffraction structural analysis of this product was carried out and feasibility was demonstrated for the nucleophilic substitution of the trinitromethyl group in this compound by the action of phenol, phenol derivatives, and thiophenol.Keywords: condensed tetrazolo-1,3,5-triazines, 5-aryloxy-3-methyl-and 5-arylthio-3-methyltetrazolo[1,5-a]-1,3,5-triazin-7-ones, 3-methyl-5-trinitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one, alkylation, nucleophilic substitution of the trinitromethyl group.In a continuation of a study of condensed tetrazolo-1,3,5-triazines [1], we synthesized covalent derivatives of substituted tetrazolo[1,5-a]-1,3,5-triazin-7-one by the alkylation of various salts of 5-trinitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one using methyl iodide in DMF and acetonitrile. Alkylation could not be obtained using the tetramethylammonium salt of 5-trinitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one (1a) [1] despite broad variation of the reaction conditions such as the solvent, reaction temperature, and reaction time. The desired product could be obtained by alkylation only through use of the silver salt of 5-trinitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one [2].