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Synthesis of 2-(6-nitrobenzofuroxan-4-yl)-2H-[1,2,3]triazolo-[4,5-e][1,2,3,4]tetrazine 4,6-dioxide
Russian Chemical Bulletin ( IF 1.7 ) Pub Date : 2020-04-01 , DOI: 10.1007/s11172-020-2826-3
A. O. Shvets , A. A. Konnov , M. S. Klenov , A. M. Churakov , Yu. A. Strelenko , V. A. Tartakovsky

At heating of 2-(2-azido-3,5-dinitrophenyl)-2H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 4,6-dioxide in toluene at 110 °C, the azido group interacts mainly with the neighboring nitro group and to a lesser extent with the neighboring 1,2,3-triazole ring, resulting in 2-(6-nitrobenzofuroxan-4-yl)-2H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 4,6-dioxide (2) in 68% yield, as well as 8,10-dinitro-5,11-dehydro-5H,11H-[1,2,3,4]tetrazino[5′,6′:4,5]-[1,2,3]triazolo[2,1-a][1,2,3]benzotriazole 1,3-dioxide and 8,10-dinitro-5,11-dehydro-5H,11H-[1,2,3,4]tetrazino[5′,6′:4,5][1,2,3]triazolo[2,1-a][1,2,3]benzotriazole 2,4-dioxide in 5% yields respectively. Furoxan 2 may be of interest as an energetic compound due to the combination of good thermal stability, positive estimated enthalpy of formation (ΔH°f = 1005 kJ mol−1) and optimal density.

中文翻译:

2-(6-nitrobenzofuroxan-4-yl)-2H-[1,2,3]triazolo-[4,5-e][1,2,3,4]四嗪4,6-dioxide的合成

在加热 2-(2-叠氮基-3,5-二硝基苯基)-2H-[1,2,3]三唑并[4,5-e][1,2,3,4]四嗪 4,6-二氧化物时在 110 °C 的甲苯中,叠氮基主要与相邻的硝基相互作用,并在较小程度上与相邻的 1,2,3-三唑环相互作用,产生 2-(6-硝基苯并呋喃-4-基)-2H-[ 1,2,3]三唑并[4,5-e][1,2,3,4]四嗪4,6-二氧化物(2),产率为68%,以及8,10-二硝基-5,11- dehydro-5H,11H-[1,2,3,4]tetrazino[5',6':4,5]-[1,2,3]triazolo[2,1-a][1,2,3]苯并三唑 1,3-二氧化物和 8,10-二硝基-5,11-脱氢-5H,11H-[1,2,3,4]tetrazino[5',6':4,5][1,2,3 ]三唑并[2,1-a][1,2,3]苯并三唑2,4-二氧化物,产率分别为5%。由于良好的热稳定性、正估计的生成焓 (ΔH°f = 1005 kJ mol-1) 和最佳密度,呋喃 2 可能作为一种高能化合物而受到关注。
更新日期:2020-04-01
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