Fluorodinitroethoxy furazan pyrazine compounds and synthesis method thereof

A technology of fluorodinitroethoxyfurur and dinitroethoxy, which is applied in the field of energetic material synthesis, can solve the problems of high solvent toxicity and insufficient mild reaction conditions, and achieve simple steps, mild synthesis conditions, and extensive The effect of applying the foreground

Inactive Publication Date: 2021-06-29
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The solvents used in the above two methods are more toxic and the reaction conditions are not mild enough

Method used

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  • Fluorodinitroethoxy furazan pyrazine compounds and synthesis method thereof
  • Fluorodinitroethoxy furazan pyrazine compounds and synthesis method thereof
  • Fluorodinitroethoxy furazan pyrazine compounds and synthesis method thereof

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preparation example Construction

[0028] The preparation method of the target product of the present invention comprises the following steps: (1) dissolving 5,6-dichlorofurazo[3,4-b]pyrazine (1) in dichloromethane, adding 2-fluoro-2,2-dinitroethanol, 2,4,6-collidine, then stirred, filtered through a short column of silica gel, eluted with dichloromethane and the eluent was concentrated under reduced pressure , to obtain 5-chloro-6-(2-fluoro-2,2-dinitroethoxy)furazo[3,4-b]pyrazine (2); (2) compound 5-chloro-6 -(2-Fluoro-2,2-dinitroethoxy)furazo[3,4-b]pyrazine (2) was dissolved in dichloromethane, and 2-fluoro-2,2 -Dinitroethanol, 4-dimethylaminopyridine, stirred, filtered through a short column of silica gel, eluted with dichloromethane and concentrated under reduced pressure to obtain 5,6-bis(2-fluoro-2, 2-Dinitroethoxy)furazano[3,4-b]pyrazine (3).

[0029]

Embodiment 1

[0031] Synthesis of 5,6-bis(2-fluoro-2,2-dinitroethoxy)furazo[3,4-b]pyrazine:

[0032] (1) Dissolve 5,6-dichlorofurazo[3,4-b]pyrazine (1) (152mg, 0.8mmol) in dichloromethane (6mL), and add 2-fluoro-2 , 2-dinitroethanol (126mg, 0.8mmol), 2,4,6-collidine (99mg, 0.8mmol), then stirred it at room temperature (25°C) for 1h, filtered through a short column of silica gel, Elute with dichloromethane and concentrate the eluent under reduced pressure to obtain 5-chloro-6-(2-fluoro-2,2-dinitroethoxy)furazo[3,4-b]pyridine azine (2). (2) Compound 2 (200mg, 0.65mmol) was dissolved in dichloromethane (4mL), and 2-fluoro-2,2-dinitroethanol (100mg, 0.65mmol), 4-dimethyl Aminopyridine (80 mg, 0.65 mmol). The reaction was stirred at room temperature (25°C) for 1 h, filtered through a short column of silica gel, eluted with dichloromethane and the eluent was concentrated under reduced pressure to obtain 5,6-bis(2-fluoro-2,2-bis Nitroethoxy)furazo[3,4-b]pyrazine (3) (240 mg, 87% yield). Its c...

Embodiment 2

[0037] The reaction temperature of step (1) and step (2) is 40 DEG C, and other conditions are the same as Example 1, and the yield is 72%.

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Abstract

The invention discloses fluorodinitro ethyoxyl furazan pyrazine compounds and a synthesis method thereof. 5, 6-dichlorofurazano[3, 4-b]pyrazine used as a raw material is subjected to nucleophilic substitution with fluorine dinitroethanol in dichloromethane to obtain the target compounds 5, 6-di(2-fluoro-2, 2-dinitroethyoxy)furazano[3, 4-b]pyrazine. The synthesis route is simple and easy to implement, and reference can be provided for synthesis of the fluoro dinitroethyoxy energetic derivative; and the target compounds are excellent in performance, can be applied to the field of propellants or explosives, and have high mechanical and thermal sensitivity and good detonation performance.

Description

technical field [0001] The invention belongs to the field of energetic material synthesis, and relates to a furazanopyrazine compound and a synthesis method thereof. Background technique [0002] The introduction of fluorodinitroethyl into the heterocycle can not only improve the detonation performance of the compound, but also improve the thermodynamic stability of the compound, which has become an important research direction in the field of energetic materials. [0003] At present, there are two main methods for constructing energetic compounds by substituting halogen atoms with fluorodinitroethyl groups: (1) using acetone as the reaction solvent and sodium phosphate dodecahydrate as the basic catalyst to synthesize fluorodinitroethyl-substituted halogen atoms; Energy compounds (Chemistry Select, 2017, 2(16): 4567-4571). (2) Using triethylamine as a reaction catalyst and heating to 80°C to synthesize energetic compounds substituted with fluorodinitroethyl groups (New Jou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/04C06B25/34
CPCC07D498/04C06B25/34
Inventor 陆国平张帅谢舒丰
Owner NANJING UNIV OF SCI & TECH
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