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Substituted [1,2,4]triazolo[4,3-b] [1,2,4,5] tetrazine compounds and preparation thereof

A 3-b, triazolo technology, applied in the directions of nitrated acyclic/alicyclic/heterocyclic amine explosive compositions, organic chemistry, etc., can solve the problem that there is no report on the energetic properties of compounds, and the introduction of energetic groups such as nitro groups And other issues

Active Publication Date: 2018-08-24
BEIJING INSTITUTE OF TECHNOLOGYGY
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Problems solved by technology

However, the synthesis of compounds with energetic groups at the 3- and 6-positions of [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine has not been reported yet
[0003] In 1998, David E.Chavez synthesized a series of triazolotetrazine compounds, but their research group did not introduce energetic groups such as nitro groups on this skeleton (David E.Chavez, Michael.A.Hiskey, Synthesis of the Bi-Heterocyclic Parent Ring System 1,2,4-Triazolo[4,3-b][1,2,4,5]Tetrazine and Some 3,6-Disstituted Derivatives, J.Heterocyclic chem.,1998,35, 1239.)
In 2012, Aleksei B. Sheremetev synthesized a series of triazolotetrazine compounds. It can be seen from the single crystal structure that triazolotetrazine has good coplanarity, but their research group has no research on this kind of compounds. Energetic properties were reported, and no energetic groups such as nitro were introduced into this parent ring (Nadezhda V.Palysaeva, KaterinaP.Kumpan, Aleksei B.Sheremetev, A Direct Approach to a 6-Hetarylamino[1,2,4] triazolo[4,3-b][1,2,4,5]tetrazine Library Org. Lett. 2014, 16, 406-409.)

Method used

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  • Substituted [1,2,4]triazolo[4,3-b] [1,2,4,5] tetrazine compounds and preparation thereof
  • Substituted [1,2,4]triazolo[4,3-b] [1,2,4,5] tetrazine compounds and preparation thereof
  • Substituted [1,2,4]triazolo[4,3-b] [1,2,4,5] tetrazine compounds and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056]In a 100mL one-mouth bottle, 500mg (2.3mmol) 6-(3,5-dimethyl-pyrazol-1-yl)-[1,2,4]triazolo[4,3-b][1, 2,4,5] Tetrazine (see the following literature for its preparation: David E.Chavez, Michael.A.Hiskey, Synthesis of the Bi-Heterocyclic Parent Ring System 1,2,4-Triazolo[4,3-b] [1,2,4,5]Tetrazine and Some 3,6-Disstituted Derivatives, J.Heterocylic chem.,1998,35,1239.) was dissolved in 50mL of methanol, and 359.6mg (2.8mmol) of 3-amino-5 -Nitro-[1,2,4]furazan (for its preparation, see the following literature: F.Pang, G.Wang, T.Lu, G Fan, F.-X.Chen, Preparation and characteristics of 1,2, 4-oxadiazole-derived energetic ionic salts with nitrogen linkages, New J.Chem., 2018, 42, 4036-4044.), and then add 283.3mg (2.8mmol) triethylamine to obtain a reaction solution; the reaction solution was reacted at 50°C After 8 hours, cool to room temperature, add 100 mL of water to the reaction solution for dilution, and adjust the pH to 2 with 1mol / L HCl, then extract with ethyl acetat...

Embodiment 2

[0062] In a 250mL single-necked bottle, 2g (8.6mmol) of 3-amino-6-(3,5-dimethyl-pyrazol-1-yl)-[1,2,4]triazolo[4,3-b ][1,2,4,5]tetrazine was dissolved in 100mL acetonitrile, added 1.35g (10.4mmol) 3-amino-5-nitro-[1,2,4]furazan, then added 1.3g (9.5 mmol) potassium carbonate, followed by reflux reaction for 5 days, cooled to room temperature, adding 100mL water to the reaction solution for dilution, and adjusting the pH to 1.5 with 3mol / L HCl, then extracting with ethyl acetate, and using saturated Wash with sodium chloride, and dry with sodium sulfate, carry out underpressure distillation to remove organic solvent at 0.01MPa and 30 DEG C with rotary evaporator again, separate with silica gel column chromatography (V 甲醇 :V 二氯甲烷 =1:10), and then use a rotary evaporator at 0.01MPa and 30°C to carry out rotary evaporation of the separated organic phase to remove the organic solvent, to obtain the solid product 3-amino-6-N-(5-nitro-[1 ,2,4]furazan-3-yl)-[1,2,4]triazolo[4,3-b][1,2...

Embodiment 3

[0068] In a 50mL three-necked flask, 250mg (0.94mmol) of 3-amino-6-N-(5-nitro-[1,2,4]furazan-3-yl)-[1,2,4]triazolo [4,3-b][1,2,4,5]tetrazine (see Example 2 for its preparation) was added to 6.5mL 2mol / L H 2 SO 4 6.5mL sodium nitrite (130.1mg, 1.89mmol) aqueous solution was added in an ice-water bath to obtain a reaction solution; after the reaction solution was reacted at 30°C for 2h, it was extracted with ethyl acetate, and the extracted organic phase was washed with saturated Wash with sodium chloride, and dry with sodium sulfate, then carry out vacuum distillation to remove solvent at 0.01MPa and 30 ℃ with rotary evaporator, then use silica gel column chromatography to separate (V 甲醇 :V 二氯甲烷 =1:20), and then use a rotary evaporator at 0.01MPa and 30°C to carry out rotary evaporation of the separated organic phase to remove the organic solvent to obtain a solid product 3-nitro-6-N-(5-nitro-[ 1,2,4]furazan-3-yl)-[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine.

[0069] At 20°C, ...

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Abstract

The invention relates to a substituted [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine energetic compounds and preparation thereof, and belong to the field of organic synthesis and energetic materials. Energetic groups are successfully introduced into position 3 or / and position 6 of [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine by a substitution reaction, so that the compounds have the characteristics of highenthalpy of formation, high detonation velocity and detonation pressure, good thermal stability, low mechanical sensitivity and the like, and have potential application value in the field of energetic materials. Besides, the adopted synthesis method is simple to operate and reaction conditions are mild.

Description

technical field [0001] The present invention specifically relates to a [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine containing an energetic group introduced at the 3-position or / and 6-position The invention relates to an energy compound and a preparation method thereof, belonging to the fields of organic synthesis and energetic materials. Background technique [0002] 3,6-Disubstituted-[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine is a class of [1,2,4]triazolo[ 4,3-b][1,2,4,5] The polynitrogen structure characterized by the tetrazine skeleton, based on [1,2,4]triazolo[4,3-b][1,2,4, 5] Tetrazine-based energetic materials have been studied in calculations for many years (Tao Wei, Weihua Zhu, Heming Xiao et al., DFT study on energetic tetrazolo-[1,5-b]-1,2,4, 5-tetrazine and 1,2,4-triazolo-[4,3-b]-1,2,4,5-tetrazine derivatives[J], Journal of Hazardous Materials 179(2010)581–590; Sonal Deswal, Vikas D .Ghule, S.Radhakrishnan, Quantum-chemical design of tetrazolo[1,5-b][1,2,4,5]tetrazi...

Claims

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Application Information

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IPC IPC(8): C07D487/04C06B25/34
CPCC06B25/34C07D487/04
Inventor 陈甫雪王桂龙范桂娟
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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