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Synthesis method of pyrazolotriazine energetic compound

A synthesis method and technology of triazines, which are applied in the field of synthesis of pyrazolotriazine energetic compounds, can solve problems such as difficult application in actual production, insufficient reaction conditions, and high toxicity of reagents, and achieve low price, The effect of mild synthetic conditions and simple steps

Pending Publication Date: 2021-03-30
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned routes for synthesizing aza-fused ring energetic compounds are complex, the reagents used are relatively toxic, the reaction conditions are not mild enough, it is not easy to operate, and the yield is too low, so it is difficult to apply in actual production

Method used

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  • Synthesis method of pyrazolotriazine energetic compound
  • Synthesis method of pyrazolotriazine energetic compound
  • Synthesis method of pyrazolotriazine energetic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Synthesis of 5-amino-3,4-dinitro-1H-pyrazole

[0031]

[0032] 3,4-Dinitro-1H-pyrazole (1g, 6.33mmol) was dissolved in dimethylsulfoxide (30mL), potassium tert-butoxide (2.84g, 2.53mmol), 4-amino- 4H-1,2,4-triazole (ATA) (1.28 g, 1.52 mmol). The reactant was stirred at 50°C for 8 h, extracted with ethyl acetate, washed with saturated NaCl solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain crude 5-amino-3,4-dinitro-1H-pyrazole.

[0033] (2) Synthesis of 4-amino-3,7,8-trinitropyrazole-[5,1-c][1,2,4]triazine

[0034]

[0035] At 0°C, add 20 mL of 10% H to the crude 5-amino-3,4-dinitro-1H-pyrazole 2 SO 4 , and NaNO dissolved in 2.4 mL of water 2 (240 mg, 3.48 mmol) solution was added dropwise to the cooled dispersion, and the mixture was stirred for 2 h to form the corresponding diazonium salt in situ. NaOH (783 mg, 19.58 mmol) and nitroacetonitrile (538 mg, 6.25 mmol) were dissolved in 6 mL of ice water to pre...

Embodiment 2

[0039] Synthesis of 3-nitropyrazolo[5,1-c][1,2,4]triazin-4-amine

[0040]

[0041] The preparation method is the same as that in Preparation Example 1, except that the pyrazole derivative in step (1) uses pyrazole, and finally synthesizes 3-nitropyrazolo[5,1-c][1,2,4]tri The yield of azin-4-amine was 37%.

[0042] 1 H NMR (500MHz, DMSO-d 6 )δ9.48(s,2H),8.35(s,1H),7.11(s,1H)ppm.

[0043] 13 C NMR (126MHz, DMSO-d 6 )δ105.91, 130.69, 138.84, 140.51, 145.32ppm.

Embodiment 3

[0045] Synthesis of 7-methyl-3-nitropyrazolo[5,1-c][1,2,4]triazin-4-amine

[0046]

[0047] The preparation method is the same as in Preparation Example 1, except that the pyrazole derivative in step (1) is 3-methyl-1H-pyrazole, and finally synthesizes 7-methyl-3-nitropyrazolo[5, The yield of 1-c][1,2,4]triazin-4-amine was 43%.

[0048] 1 H NMR (500MHz, DMSO-d 6 )δ9.34(s,2H),7.91(s,1H),2.23(s,3H)ppm.

[0049] 13 C NMR (126MHz, DMSO-d 6 )δ21.13, 101.84, 129.52, 136.24, 141.79, 149.28ppm.

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Abstract

The invention discloses a synthesis method of a pyrazolotriazine energetic compound. The method comprises the following steps: firstly, taking a pyrazole derivative as a raw material, obtaining an intermediate product 5-aminopyrazole derivative through a VNS ammoniation method, and then carrying out diazo coupling and cyclization on the 5-aminopyrazole derivative and nitroacetonitrile sodium saltto obtain the target compound pyrazolotriazine compound. The target compound can be obtained through two-step reaction, wherein the synthesis steps are shortened, the total reaction yield and safety in the reaction process are improved, and the prepared target compound is excellent in performance, high in mechanical and thermal sensitivity and good in detonation performance and is suitable for thefield of propellants and explosives.

Description

technical field [0001] The invention belongs to the field of energetic material synthesis and relates to a method for synthesizing pyrazolotriazine energetic compounds. Background technique [0002] In the design of novel high energy density compounds, fused ring compounds have attracted extensive attention due to their novel properties. The research results show that various nitrogen-heterofused ring compounds can be obtained from diazoazole and nitroacetonitrile sodium salt, and the existence of nitro and amino groups in the nitrogen-hetero-fused ring system can further increase the density and stability of molecules through hydrogen bond interactions , is a new method to construct insensitive high-energy compounds. [0003] At present, the synthesis of pyrazolotriazine aza-condensed ring energetic compounds requires the introduction of an amino group at No. 5 on the pyrazole ring, and the introduction of amino groups is relatively complicated, which ultimately leads to a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 蔡春张帅陆国平
Owner NANJING UNIV OF SCI & TECH
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