Condensed Tetrazolo-1,3,5-triazines. 1. Synthesis of 5-Polynitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one Salts

Abstract

Investigations of the synthesis and chemical properties of nitro-and polynitromethyl derivatives of 1,3,5-triazine have been actively carried out in recent years [1][2][3][4][5][6][7][8][9]. Our work is also based on a study of the reactivity of trinitromethyl derivatives of 1,3,5-triazine and concerns the potential synthesis of previously unreported polynitromethyltetrazolo-1,3,5-triazines in which a tetrazole ring is annelated to the 1,3,5-triazine ring.The general method for preparing condensed tetrazoles is based on the annelation of tetrazole to the triazine ring via an azido-tetrazole tautomeric conversion of the azidoazomethine fragment in the molecule [10,11]. For azido-1,3,5-triazines which contain electron-donor substitutents this question has been considered in [12,13].NaN 3 3a, 4a R 1 = R 2 = Me; 3b, 4b R 1 = R 2 = Et __________________________________________________________________________________________

Synthesis and cytotoxic activity of trinitromethyl derivatives of 1,3,5-triazine

“…Compounds I -III were synthesized as described in [4] and compound VIII was synthesized as described in [6]. IR spectra were taken on an Avatar 360ESP spectrophotometer in KBr tablets.…”

“…IR spectra were taken on an Avatar 360ESP spectrophotometer in KBr tablets. PMR spectra were recorded using a Bruker AM300 spectrometer (300 MHz), the spectra of compounds I -III, VI, and VII being recorded in acetone-d 6 and that of compound VIII in DMSO-d 6 , using HMDS as the internal standard. Elemental analysis data corresponded to calculated values.…”

“…R = CH 2 CH 2 Cl (I); R = CH 2 Ph (II); R = cyclo-C 6 H 11 (III) 2,4-Diamino-6-trinitromethyl-1,3,5-triazines (VI -VII) were prepared by nucleophilic substitution of the trinitro-methyl group in the corresponding 2-amino-4,6bis(trinitromethyl)-1,3,5-triazines (IV-V), which we synthesized previously as described in [5], in the presence of amines. R 1 = R 2 = Me (IV, VI); R 1 = R 2 = Et (V, VII) 2-Dimethylamino-4-azido-6-trinitromethyl-1,3,5-triazine (VIII) was synthesized by interaction of 2-dimethylamino-4,6-bis(trinitromethyl)-1,3,5-triazine (IV) with sodium azide as described in [6].…”

Energetic Co-Crystal of a Primary Metal-Free Explosive with BTF. Ideal Pair for Co-Crystallization

“…The starting co-formers, tetramethylammonium 5-(trinitromethyl)tetrazolo [1,5-a] [1,3,5] triazin-7-olate (1) [34] and benzotrifuroxan (BTF, 2) [37], were obtained according to published procedures. BTF (1 eq) and salt 1 (2 eq) were added to ethanol (50 eq) and heated with stirring until complete dissolution.…”

“…In an earlier communication we disclosed our initial results on the discovery of energetic 5-(trinitromethyl)tetrazolo [1,5-a] [1,3,5]triazine structures [34], among which tetramethylammonium salt of 7-oxo-5-(trinitromethyl)-4,5,6,7-tetrahydrotetrazolo [1,5-a] [1,3,5]triazin-5-ide (1) is a potential metal-free primary explosive. However, despite the acceptable sensitivity to heat and shock, the density and energetic performance (see below) of this compound should be increased.…”