Oxygen‐Rich 1,2,4‐Triazolo[3,4‐d]‐1,2,4‐triazolo[3,4‐f]furazano[3,4‐b]pyrazines as Energetic Materials

Abstract

Oxygen-Rich 1,2,4-Triazolo [3,4-d]-1,2,4-triazolo[3,4-f]furazano [3,4b]pyrazines as Energetic Materials Aleksei B. Sheremetev,* [a] Vecheslav L. Korolev, [a] AleksandrA.P otemkin, [a, b] Abstract: Ac onvenient one-pot synthesis of 5,10-bis(trinitromethyl)-(5)a nd 5,10-bis(fluorodinitromethyl)furazano[3,4e]di([1,2,4]triazolo)[4,3-a:3',4'-c]pyrazines (6)b ye mploying the reaction of 5,6-dichlorofurazano[3,4-b]pyrazine with 5-(trinitromethyl)-and 5-(1-fluoro-1,1-dinitromethyl)tetrazoles, respectively,w as developed. The protocol was carriedo ut under mild conditions at am oderate temperature and over short reaction times to synthesize the products in excellent yields. For the first time, thesep olynitromethyl-substituted compounds, whichm ay have potential use as explosive and propellant materials,h ave been fully characterized. The burningr ate of compound 5 was shown to be slightly superior to that of 2,4,6,8,10,12-hexanitrohexaazaisowurtzitane (CL-20).[a] Prof. A. B. Sheremetev,V .L.Korolev,A .A.P otemkin, N.

Synthesis and Characterization of 3‐(5‐(Fluorodinitromethyl)‐1H‐1,2,4‐triazol‐3‐yl)‐4‐nitrofurazan: A Novel Promising Energetic Component of Boron‐based Fuels for Rocket Ramjet Engines

“…3-Nitro-4-(1H-1,2,4-triazol-3-yl)-furazan (4). Compound 2 (0.5 g, 2.1 mmol) was added in small portions to as olution of Na 2 WO 4 2H 2 O( 0.82 g, 2.5 mmol) in am ixture of H 2 O 2 (37 %, 5.7 mL) with H 2 SO 4 (95 %, 2.9 mL) at r.t. After addition, the mixture was stirred at 50 8Cf or 3h.T he cooled mixture was poured into ice water (20 mL) 3136,2894,1601,1561,1523,1457,1400,1387,1358,1307,1236,1182,1105,1032,989,968,872,827 3103,3002,2972,1771,1761,1731,1594,1562,1453,1399,1389,1376,1331,1246,1213,1170,1114,1074,1015,983,828 Ethyl 2,2-dinitro-2-(3-(4-nitrofurazan-3-yl)-1H-1,2,4-triazol-5-yl)acetate (5). Compound 3 (0.27 g,1mmol) was added in small portions to am ixture of H 2 SO 4 (3.5 mL, 95 %) and HNO 3 (2.1 mL, 100 %) at 0 8C.…”

“…While many potent energetic furazans bearing fluorodinitromethyl moiety, C(NO 2 ) 2 F, have been reported, very few syntheses of energetic 1,2,4‐triazoles which incorporate this moiety at a carbon atom of the ring have been described (Figure ). The design and synthesis of new oxygen‐rich energetic compounds with high density and improved performance has been the focus of recent studies in our group .…”

“…[2] In efforts to modulate andf ine-tune the properties of such furazan precursors, recent efforts have focused on the combination of the furazanr ing with the othersn itrogen heterocycles. [3,4] Recent work by our group [5] and others [6] has shown the synthesis and functionalization of frameworks on the base of furazan-1,2,4-triazole combinations to be an efficient way of generating attractive target high nitrogen compounds.…”

Energetic Triazolo‐Triazolo‐Furazano‐Pyrazines: A Promising Fused Tetracycle Building Block with Diversified Functionalities and Properties

“…[7] There are many experimental results for explosives and propellants containing fused rings demonstrated the promising and fascinating energetic properties with sufficient stability and insensitivity to mechanical stimuli. [8][9][10][11][12][13][14][15][16][17][18] The differences in physicochemical properties of individual heterocyclic and carbocyclic rings would be overcome in the fused backbone and will help to achieve better energetic performance and stability (see Figure 1).…”

“…The TTFP structure (molecular formula) is tetracycle consists of four fused rings including pyrazine, furazan, and two triazole rings. In the literature, the synthesis of TTFP has been reported, [31][32][33][34] however, the design of new HEMs with TTFP backbone composed of different explosophoric groups is not known. Our objective in this paper is to address the importance of TTFP fused backbone in designing the energetic molecules and also look at the relative role of À NH 2 , À NHNO 2 , À ONO 2 , À NO 2 , and À N 3 groups in determining the energetic properties.…”