Synthesis and properties of 1,2,4-triazolo[4,3-d]-1,2,4-triazolo-[3,4-f]furazano[3,4-b]pyrazines

Khisamutdinov, G. Kh.; Korolev, V. L.; Parkhomenko, T. N.; Sharonova, V. M.; Artem'eva, Elena; Abdrakhmanov, I. Sh.; Smirnov, S. P.; Уграк, Б. И.

doi:10.1007/bf00697044

Cited by 12 publications

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“…With the triazolyl acetate 3 in hand, we were able to look at CH 2 nitration of its acetate moiety.W ee nvisioned aK hisamutdinov nitration [18] may be applicable in this case. The nitration of compound 3 was found to proceed cleanly with 100 % HNO 3 /95 %H 2 SO 4 at 0-5 8Cf or 1hand follow stirring up to 3d at ambient temperature.…”

Section: Resultsmentioning

confidence: 99%

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

Sheremetev

Aleksandrova

Semyakin

et al. 2019

Chemistry An Asian Journal

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The synthesis of a new energetic 1,2,4‐triazole compound bearing nitrofurazanyl and fluorodinitromethyl units, which may find use as a component for rocket ramjet engines (RRE), is described. The target product was prepared in a four‐step process applying oxidation/nitration/decarboxylation/fluorination reactions and is fully characterized. Its density and structural features were uniquely determined by X‐ray analysis. It is shown that replacing HMX with the compound of this study in boron‐based fuels gives an increase in energy.

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Section: Resultsmentioning

confidence: 99%

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

Sheremetev

Aleksandrova

Semyakin

et al. 2019

Chemistry An Asian Journal

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“…Recrystallization of the crude product (HNO 3 )g ave pure compound 5 (2.7 g, 54 %) as aw hite solid, which decomposed upon melting at 129-130 8C; ref. [10] m.p. 128 8C( dec).…”

Section: Methodsmentioning

confidence: 99%

“…[12,21,22] However,e xamples, in which this transformationh as been employed, use al imited number of 5-substituted tetrazole precursors. To the best of our knowledge,s uch ar eaction that uses 5-(nitroalkyl)tetrazoles has not been re- Scheme1.Previoussynthesis of compound 5.R eagents and conditions: [10] ported to date. We, therefore, proceeded to explore the participation of 5-(trinitromethyl)tetrazoles in the formation of compound 5.This new protocoliss hown in Scheme 2.…”

Section: Synthesismentioning

confidence: 99%

“…Oxygen-rich compounds are useful in the processing of energetic formulations.T ypically, compounds with an oxygen balance close to zero yield ah igherp erformance. An interesting molecule is 5,10-bis(trinitromethyl)furazano [3,4- [10] (Scheme 1). Althought hey describe the preparation of the molecule, only IR and NMR data are presented without any crystal structures or details of its physicala nd energetic properties.…”

Section: Introductionmentioning

confidence: 99%

“…The previous synthesis of compound 5 was accomplished in af ive-step sequence (Scheme 1) [10] by startingf rom available 5,6-dichlorofurazano[3,4-b]pyrazine (7). [11] Chloride displacement by treatment with hydrazine gave dihydrazinylc ompound 8 followed by its conversion into tetracyclic acid ester 9 using ethyl 3-ethoxy-3-iminopropanoate hydrochloride.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2016

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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.

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

2020

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In this study, high energy materials (HEMs) derived from 1,2,4‐triazolo[3,4‐d]‐1,2,4‐triazolo[3,4‐f]furazano[3,4‐b]pyrazine (TTFP) substituted with −NH2, −NHNO2, −ONO2, −NO2, and −N3 explosophoric groups were designed and computationally characterized. Density functional calculations with B3PW91/6‐31G(d,p) method were used to explore the optimized structures, energetic properties, and sensitivity of TTFP derivatives. It is found that the TTFP is an effective molecular backbone for improving the energy content and energetic performance of the designed compounds. The effect of various explosophoric groups on energy content, density, detonation performance, and sensitivity was investigated. The energetic evaluation indicated that TTFP derivatives having −NHNO2 (F4), −ONO2 (F5), and −NO2 (F6) groups demonstrate good detonation performances and exceed the performance of TNT and close to that of RDX. Compounds F4‐F6 displays the best energetic properties (density > 1.85 g/cm3, detonation velocity >8.30 km/s, detonation pressure > 32.0 GPa). Considering the energetic properties, the TTFP backbone can be regarded as an energy‐rich unit, which can be substituted with suitable explosophoric groups for constructing HEMs.

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Synthesis and properties of 1,2,4-triazolo[4,3-d]-1,2,4-triazolo-[3,4-f]furazano[3,4-b]pyrazines

Cited by 12 publications

References 0 publications

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

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

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

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

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