Synthesis of 4,4'-dinitro-1H,1'H-[3,3'-bipyrazole]-5,5'-diamine

Шкинева, Т. К.; Kormanov, Alexandr V.; Boldinova, Valeriya N.; Вацадзе, И. А.; Далингер, И. Л.

doi:10.1007/s10593-018-2336-5

Cited by 15 publications

(7 citation statements)

References 33 publications

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“…Acidic hydrolysis of the cyano groups in bipyrazole 75 a at 50–60 °C gave the amide 62 and treatment of 75 b with triphenylphosphine at room temperature gave the diphosphimine 76 . Hofmann rearrangement of either amide 62 or the diphosphimine 76 led to the corresponding diamine 63 in a satisfactory yield [62] …”

Section: Synthetic Routes To Bipyrazolesmentioning

confidence: 99%

Synthetic Routes to Bioactive Bipyrazole Derivatives

Dawood

Abbas

2021

ChemistrySelect

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The synthetic routes to six differently connected bipyrazole systems 1,1′‐, 1,3′‐ and 1,4′‐, 3,3′‐, 3,4′‐ and 4,4′‐bipyrazoles are thoroughly reported. Two main synthetic platforms are outlined; i) cyclocondensation reactions of tetraketones or pyrazoles having difunctional moieties with hydrazines, or pyrazolyl‐hydrazines with difunctional substrates, ii) 1,3‐dipolar cycloaddition of nitrilimines with bis‐olefines, or bis‐nitrilimines with activated alkenes and alkynes. Many of the reported bipyrazoles have potent applications; in pharmaceutical and material science areas.

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Section: Synthetic Routes To Bipyrazolesmentioning

confidence: 99%

Synthetic Routes to Bioactive Bipyrazole Derivatives

Dawood

Abbas

2021

ChemistrySelect

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“…(a) Gas-phase heats of formation for selected azoles and oxadiazoles. [9,16] (b) Literature known explosives based on linked pyrazoles and tetrazoles: TN-4,4'-BP (tetranitro-4,4'-bipyrazole), [26] TN-3,3'-BP (tetranitro-3,3'-bipyrazole), [27] TKX-50 (dihydroxylammonium 5,5Ј-bitetrazole-1,1Ј-dioxide), [14] DNNPENT (N-(1-(2-(3,4-dinitro-5-(nitroamino)-pyrazol-1-yl)ethyl)-5H-tetrazol-5-ylidene)nitramide). [28]…”

Section: Introductionmentioning

confidence: 99%

Combining Performance with Thermal Stability: Synthesis and Characterization of 5‐(3,5‐Dinitro‐1H‐pyrazol‐4‐yl)‐1H‐tetrazole and its Energetic Derivatives

Benz

Klapötke

Stierstorfer

2020

Zeitschrift anorg allge chemie

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In this study, we present the synthesis of 5‐(3,5‐dinitro‐1H‐pyrazol‐4‐yl)‐1H‐tetrazole and its energetic derivatives starting from 4‐amino‐3,5‐dinitropyrazole, which was diazotized and cyanide substituted. A subsequent cycloaddition reaction with sodium azide led to 5‐(3,5‐dinitro‐1H‐pyrazol‐4‐yl)‐1H‐tetrazole (3). Several alkaline metal and nitrogen‐rich salts were prepared and characterized by low‐temperature X‐ray diffraction. Additionally, all compounds were analyzed by vibrational spectroscopy (IR), 1H, 13C and 14N NMR spectroscopy, elemental analysis and differential thermal analysis (DTA). Additionally, the heats of formation for selected compounds were calculated using the atomization method based on CBS‐4M enthalpies as well as important detonation parameters by using the EXPLO5 code (V6.05). Furthermore, the sensitivities of 3 and all synthesized salts toward friction, impact and electrostatic discharge according to BAM (Bundesamt für Materialforschung) were determined and compared to RDX.

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“…Direct nitration of amino-substituted reactants is an important process for preparation of nitramino products. Various nitration methods have been reported such as use of a mixture of concentrated sulfuric acid and nitric acid, − fuming (100%) nitric acid, ,− or HNO 3 /Ac 2 O/TFA. − However, the reaction yields are often low or require quite low reaction temperatures and often large amounts of harmful waste acid result, which create serious environmental issues. Therefore, developing a green, mild, and efficient approach for the synthesis of nitramino-based compounds is highly desirable.…”

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confidence: 99%

“…3,5-Diamino-4-nitropyrazole ( I ) was prepared according to the literature. − Many attempts to nitrate it have failed. By following a typical procedure on nitration of amino-substituted pyrazole derivatives, , the nitrating system (HNO 3 /Ac 2 O/TFA) was tried, and the dinitramino product ( I′ ) was isolated. However, the yield is low (10%), and the product is also quite sensitive to mechanical interactions.…”

mentioning

confidence: 99%

“…Use of such a protocol is reasonably safe since it is not necessary to isolate the extremely sensitive neutral dinitramino compound. Similarly, the nitrating system (HNO 3 /Ac 2 O/TFA) was used to nitrate compound II according to the literature, but the yield was quite low and sometimes no product ( II′ ) was obtained. The nitrating mixture (KNO 3 /H 2 SO 4 ) was then employed to introduce dinitramino groups into II , which were subsequently reacted with nitrogen-rich bases to form salts 5 – 7 in high yields.…”

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Green Synthetic Approach for High-Performance Energetic Nitramino Azoles

et al. 2019

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A mild and efficient strategy for the nitration of aminosubstituted pyrazoles/triazole employing a mixture of potassium nitrate and concentrated sulfuric acid (KNO 3 /H 2 SO 4 ) as a nitrating reagent proceeded smoothly to give nitramino-substituted products. These were treated with corresponding bases to give energetic salts 1− 10. The compounds were fully characterized, and single crystal X-ray diffraction studies were obtained for 1, 4, 6, and 10. The physical properties and detonation performance were measured or calculated. Salts 1, 2, 6, 8, and 9 exhibited excellent detonation performance and acceptable sensitivities as well as good stabilities, which suggested that they have potential to be useful as highperformance explosives.

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Synthesis of 4,4'-dinitro-1H,1'H-[3,3'-bipyrazole]-5,5'-diamine

Cited by 15 publications

References 33 publications

Synthetic Routes to Bioactive Bipyrazole Derivatives

Synthetic Routes to Bioactive Bipyrazole Derivatives

Combining Performance with Thermal Stability: Synthesis and Characterization of 5‐(3,5‐Dinitro‐1H‐pyrazol‐4‐yl)‐1H‐tetrazole and its Energetic Derivatives

Green Synthetic Approach for High-Performance Energetic Nitramino Azoles

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