Synthese substituierter 1,2,3-Benzotriazin-4(3H)-on-N ²-oxide und heteroanellierter 1,2,3-Triazin-4(3H)-on-N ²-oxide

Detonation performance enhancement through a positional isomerism modification strategy

“…All reagents were purchased from Sigma-Aldrich or Energy Chemicals and were used without further purifications; the starting material ANPO was synthesized using a method reported in the literature. 6b The 1 H and 13 C NMR spectra were recorded on a Bruker AVL300 spectrometer; chemical shifts were determined with respect to external SiMe 4 ( 1 H: 400.0 MHz, 13 C: 100.0 MHz). IR spectra were recorded on a PerkinElmer Spectrum BX-FTIR spectrometer.…”

“…The precipitate was collected to give NPT (2.33 g, 9.4 mmol) in a yield of 94%. DSC (5 1C min À1 ) 274.1 1C(dec); IR (KBr, cm À1 ) 3478,3320,3021,1610,1560,1525,1488,1421,1362,1284,1160,778,685,654; 1 H NMR (400 MHz, DMSO-d 6 ) d 9.77 (s, 1H), 9.13 (s, 1H) ppm, 13 C NMR (100 MHz, DMSO-d 6 ) d 163. 5, 155.0, 154.7, 153.6, 147.8, 93.7 2,4]triazolo[5 0 ,1 0 : 2,3]pyrimido[4,5d][1,2,3]triazine 2-oxide (TPTO).…”

Intramolecular Reaction of tert‐Butyl‐NNO‐Azoxy and Cyano Groups – Novel Synthesis of Pyridazine, 1,2,3‐Triazepine, and Furan Rings

“…Dinitrile 9 was obtained after careful acidification of salt 5 with 1 N HCl to pH 5 followed by extraction with pentane and removing the solvent in vacuo at room temperature. The 1 H and 13 C NMR spectra show that in CDCl 3 solutions this compound exists as an equilibrium mixture of E/Z isomers in 4:1 ratio (see below for details).…”

“…Besides that, the intramolecular reaction of the N-nitro and the cyano groups is known, which affords 4-hydroxy-1,2,3-triazine 2-oxides. [13,14] In the course of this reaction, the cyano group is also transformed to carboxamide group followed by cyclization.…”

“…H NMR (500.1 MHz, CDCl 3 ): δ = 1.42 (s, 9 H, CMe 3 ), 2.38 (s, 3 H, Me), 6.21 (br., 2 H, NH 2 ) ppm 13. C NMR (125.8 MHz, CDCl 3 ): δ = 11.6 (Me), 26.2 (CMe 3 ), 58.7 (CMe 3 ), 111.8 (br., C-4), 112.1 (CN), 113.4 (C-3 or C-2), 132.7 (C-2 or C-3), 155.4 (C-5) ppm.…”