CN115557952B - Five-membered and seven-membered nitrogen heterocyclic compound and preparation method thereof - Google Patents
Five-membered and seven-membered nitrogen heterocyclic compound and preparation method thereof Download PDFInfo
- Publication number
- CN115557952B CN115557952B CN202211252899.7A CN202211252899A CN115557952B CN 115557952 B CN115557952 B CN 115557952B CN 202211252899 A CN202211252899 A CN 202211252899A CN 115557952 B CN115557952 B CN 115557952B
- Authority
- CN
- China
- Prior art keywords
- membered
- compound
- aza
- fused ring
- methanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims description 19
- -1 nitrogen heterocyclic compound Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 84
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 24
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 14
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- MLOXIXGLIZLPDP-UHFFFAOYSA-N 2-amino-1h-imidazole-4,5-dicarbonitrile Chemical compound NC1=NC(C#N)=C(C#N)N1 MLOXIXGLIZLPDP-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 19
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 238000003786 synthesis reaction Methods 0.000 abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 10
- 238000011160 research Methods 0.000 abstract description 4
- 238000005580 one pot reaction Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000009257 reactivity Effects 0.000 abstract description 3
- 229940125904 compound 1 Drugs 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- NDGSDCLCVGQSKB-UHFFFAOYSA-N 1h-pyrazole-4,5-dicarbonitrile Chemical compound N#CC1=CNN=C1C#N NDGSDCLCVGQSKB-UHFFFAOYSA-N 0.000 description 1
- RHEFLWRCYOAOTQ-UHFFFAOYSA-N 2-nitro-1h-imidazole-4,5-dicarbonitrile Chemical compound [O-][N+](=O)C1=NC(C#N)=C(C#N)N1 RHEFLWRCYOAOTQ-UHFFFAOYSA-N 0.000 description 1
- IVANFNGOSJTZFM-UHFFFAOYSA-N 2h-triazole-4,5-dicarbonitrile Chemical compound N#CC1=NNN=C1C#N IVANFNGOSJTZFM-UHFFFAOYSA-N 0.000 description 1
- ZPICOUKAFAPIOK-UHFFFAOYSA-N 3-amino-1h-pyrazole-4,5-dicarbonitrile Chemical compound NC1=NNC(C#N)=C1C#N ZPICOUKAFAPIOK-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention discloses a five-membered and seven-membered aza fused ring compound, which enriches the variety of aza fused ring frameworks through the fused ring compound formed by five-membered aza and seven-membered aza, widens the reactivity of the compound through the introduction of amino, lays a foundation for the research of novel energetic materials based on aza fused ring frameworks, provides a new thought, and also discloses a preparation method of the five-membered and seven-membered aza fused ring compound, which starts from known raw materials and realizes the synthesis of the novel five-membered and seven-membered aza fused ring compound through one-step reaction.
Description
Technical Field
The invention relates to the technical field of energetic materials, in particular to a five-element and seven-element nitrogen heterocyclic compound and a preparation method thereof.
Background
The energetic material is an energy material which is relevant to national strategic safety and is an energy source for the propulsion, the emission and the damage of a weapon system. With the ever-changing international forms and the development of the era, there is also an increasing demand for energetic materials, in particular for safety features, to cope with instabilities in manufacturing, transportation, use and storage.
The aza-fused ring skeleton is a skeleton formed by combining two or more aza-rings, is widely applied to low-sense high-energy energetic materials, and a novel energetic material based on the aza-fused ring skeleton has become a current research hot spot. However, at present, the aza-condensed ring skeleton is mainly limited to three kinds of five-membered ring, six-membered ring and six-membered ring, so that the number of aza-condensed ring skeletons is small, and the skeleton modification sites are usually small because the skeleton needs to be modified by high-energy groups, so that the development of novel low-sense high-energy energetic materials is limited to a certain extent. Therefore, in view of the current situation that the types of the aza-fused ring frameworks are few, development of a novel aza-fused ring framework is very important for the field of novel energetic materials.
Disclosure of Invention
It is an object of the present invention to address at least the above problems and/or disadvantages and to provide at least the advantages described below.
The invention also aims to provide a five-membered and seven-membered aza fused ring compound, which enriches the variety of aza fused ring frameworks through the fused ring compound formed by five-membered aza fused ring and seven-membered aza fused ring, widens the reactivity of the compound through the introduction of amino, lays a foundation for the research of novel energetic materials based on aza fused ring frameworks, and provides a new thought.
Still another object of the present invention is to provide a method for preparing a five-membered and seven-membered aza-fused ring compound, which starts from known available raw materials, successfully synthesizes the five-membered and seven-membered aza-fused ring compound through one-step reaction, enriches the variety of aza-fused ring skeletons, lays a foundation for the research of novel energetic materials based on aza-fused ring skeletons, and provides a new idea.
To achieve these objects and other advantages and in accordance with the purpose of the invention, there is provided a five-and seven-membered aza-fused ring compound, wherein the energetic compound has the structure of the following formula (I):
wherein X, Y is independently a carbon or nitrogen atom, R 1 、R 2 、R 3 、R 4 、R 5 Independently hydrogen, nitro or amino.
Preferably, wherein X, Y is independently a carbon or nitrogen atom, R 1 Is nitro or amino, R 2 Is hydrogen, nitro or amino, R 3 、R 4 、R 5 All are amino groups.
Preferably, wherein X is a carbon atom, Y is a nitrogen atom, R 1 Is nitro or amino, R 3 、R 4 、R 5 All are amino groups.
Preferably, wherein X is a nitrogen atom, Y is a carbon atom, R 2 Is hydrogen, nitro or amino, R 3 、R 4 、R 5 All are amino groups.
Preferably, wherein X is a carbon atom, Y is a nitrogen atom, R 1 Is amino, R 3 、R 4 、R 5 All are amino groups.
Preferably, wherein X is a nitrogen atom and Y is a nitrogen atomSon, R 3 、R 4 、R 5 All are amino groups.
The object of the invention can be further achieved by a method for preparing five-membered and seven-membered aza fused ring compounds, comprising the steps of: adding dicyano substituted five-membered nitrogen heterocycle into solvent, adding guanidine into the reaction mixture for reaction, filtering and recrystallizing after the reaction is finished to obtain the target compound of formula (I) ；
Wherein the dicyano-substituted five-membered nitrogen heterocycle has the structure of formula (II):
preferably, the molar ratio of the dicyano-substituted five-membered nitrogen heterocycle to guanidine is 1:1.0-1:1.5.
Preferably, the reaction temperature is 60-85 ℃ and the reaction time is 10-48 h.
Preferably, the solvent is one of methanol, ethanol, acetone and acetonitrile.
The invention at least comprises the following beneficial effects:
1. according to the invention, the five-membered nitrogen heterocycle and seven-membered nitrogen heterocycle form a condensed ring compound, and the five-membered and seven-membered condensed ring skeleton has better aromaticity than five-membered and five-membered condensed rings and five-membered and six-membered condensed rings, so that better stability and safety performance can be obtained. Because the seven-membered ring has more modification sites than the six-membered ring, the novel energy-containing material can be obtained more abundantly through functionalization. The invention enriches the variety of the aza-condensed ring skeleton, widens the reactivity of the compound by introducing amino, lays a foundation for researching novel energetic materials based on the aza-condensed ring skeleton, and provides a new idea.
2. The preparation method of the penta-hepta-membered aza-fused ring compound successfully synthesizes the azole energetic compound by one-step reaction from known raw materials. The synthesized azole energetic compound has potential as a high-energy material.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
Drawings
FIG. 1 is a DSC of Compound 1 of example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of compound 1 in example 1 of the present invention;
FIG. 3 is a nuclear magnetic resonance carbon spectrum of compound 1 in example 1 of the present invention.
Detailed Description
The present invention is described in further detail below with reference to the drawings to enable those skilled in the art to practice the invention by referring to the description.
It will be understood that terms, such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
The experimental methods described in the following embodiments are conventional methods unless otherwise indicated, and the reagents and materials are commercially available.
Example 1 ]
Five-membered and seven-membered nitrogen heterocyclic compound 1 has the following structural formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
2-amino-4, 5-dicyanoimidazole (133.0 mg,1.0 mmol) was dissolved in 15mL of ethanol, and a methanol solution of guanidine (64.9 mg,1.1 mmol) was added thereto at room temperature, followed by heating to 80℃and stirring for reaction for 10 hours. The reaction solution was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 1 (117.1 mg, yield 61%). The nuclear magnetic resonance hydrogen spectrum of the compound 1 is shown in figure 2, and the nuclear magnetic resonance carbon spectrum is shown in figure 3.
Example 2 ]
Which differs from example 1 in that:
the specific synthesis steps are as follows:
2-amino-4, 5-dicyanoimidazole (133.0 mg,1.0 mmol) was dissolved in 15mL of methanol, and a solution of guanidine (88.5 mg,1.5 mmol) in methanol was added thereto at room temperature, followed by heating to 70℃and stirring for reaction for 24 hours. The reaction solution was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 1 (140.2 mg, yield 73%).
Example 3 ]
Which differs from example 1 in that:
the specific synthesis steps are as follows:
2-amino-4, 5-dicyanoimidazole (133.0 mg,1.0 mmol) was dissolved in 15mL of methanol, and a methanol solution of guanidine (70.8 mg,1.2 mmol) was added thereto at room temperature, followed by heating to 70℃and stirring for reaction for 36h. The reaction solution was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 1 (155.5 mg, yield 81%).
Example 4 ]
Which differs from example 1 in that:
the specific synthesis steps are as follows:
2-amino-4, 5-dicyanoimidazole (133.0 mg,1.0 mmol) was dissolved in 15mL of acetonitrile, and a solution of guanidine (76.7 mg,1.3 mmol) in methanol was added thereto at room temperature, followed by heating to 85℃and stirring for reaction for 36h. The reaction solution was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 1 (149.8 mg, yield 78%).
Example 6 ]
Which differs from example 1 in that:
the specific synthesis steps are as follows:
2-amino-4, 5-dicyanoimidazole (133.0 mg,1.0 mmol) was dissolved in 15mL of acetone, and a methanol solution of guanidine (59.0 mg,1.0 mmol) was added thereto at room temperature, followed by heating to 60℃and stirring for 48 hours. The reaction solution was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 1 (115.2 mg, yield 60%).
Example 7 ]
Five-membered and seven-membered nitrogen heterocyclic compound 2 has the following structural formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
4, 5-dicyano-1H-1, 2, 3-triazole (119 mg, mmol) was dissolved in 10mL of acetonitrile, and a methanol solution of guanidine (70.8 mg,1.2 mmol) was added thereto at room temperature, followed by heating to 100℃and stirring for reaction for 10 hours. The reaction solution was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 2 (115.7 mg, yield 65%).
Example 8 ]
Five-membered and seven-membered nitrogen heterocyclic compound 3 has the following structural formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
2-nitro-4, 5-dicyanoimidazole (163 mg,1 mmol) was dissolved in 15mL of methanol, a solution of guanidine (70.8 mg,1.2 mmol) in methanol was added thereto at room temperature, and then the temperature was raised to 76℃and the reaction was stirred for 36h. The reaction solution was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 3 (179.8 mg, yield 81%).
Example 9 ]
Five-membered and seven-membered nitrogen heterocyclic compound 4 has the following structural formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
4, 5-dicyanopyrazole (118 mg,1 mmol) was dissolved in 10mL of methanol, a methanol solution of guanidine (70.8 mg,1.2 mmol) was added thereto at room temperature, and then the temperature was raised to 78℃and the reaction was stirred for 36h. The reaction solution was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 4 (138 mg, yield 78%).
Example 10 ]
Five-membered and seven-membered nitrogen heterocyclic compound 5 has the following structural formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
3-amino-4, 5-dicyanopyrazole (133 mg,1 mmol) was dissolved in 15mL of methanol, and a solution of guanidine (70.8 mg,1.2 mmol) in methanol was added thereto at room temperature, followed by heating to 75℃and stirring for 48 hours. The reaction solution was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 5 (138.2 mg, yield 72%).
Example 11 ]
Five-membered and seven-membered nitrogen heterocyclic compound 6 has the following structural formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
3-nitro-4, 5-dicyanopyrazole (163 mg,1 mmol) was dissolved in 15mL of methanol, and a solution of guanidine (70.8 mg,1.2 mmol) in methanol was added thereto at room temperature, followed by heating to 60℃and stirring for 48 hours. The reaction solution was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 6 (146.5 mg, yield 66%).
Example 12 ]
DSC thermogram property test experiment is carried out on five-membered and seven-membered aza fused ring compound 1 synthesized in example 1 of the invention:
compound 1 (1.0±0.1 mg) was taken for testing, test conditions: standard aluminum crucible, temperature 25-400 deg.c, heating rate 10 deg.c/min and nitrogen flow rate 50mL/min. The test results are shown in FIG. 1. As can be seen from FIG. 1, compound 1 shows a decomposition temperature of 344℃and is obtained by the sensitivity performance test: the impact sensitivity is more than 40J, the friction sensitivity is more than 360N, and the compound has excellent heat stability and safety performance.
Impact sensitivity and friction sensitivity are key factors for expressing the safety of energetic compounds, and the higher the numerical value, the more insensitive energetic materials are stable, and the safer the use and storage.
The invention enriches the variety of the aza-condensed ring skeleton by the condensed ring compound formed by five-membered aza-seven-membered aza-ring, widens the reaction activity of the compound by introducing amino, lays a foundation for researching novel energetic materials based on the aza-condensed ring skeleton, and provides a new thought. The existing aza condensed ring skeleton mainly takes five-membered ring and five-membered ring, five-membered ring and six-membered ring as main components, and the development of novel low-inductance high-energy containing materials is limited to a certain extent. The seven-membered ring has more modification sites than the six-membered ring, and can obtain a richer novel energetic material through functionalization. The invention provides a brand new five-membered ring and seven-membered ring 5/7 aza condensed ring skeleton and a preparation method thereof, wherein the skeleton has higher aromaticity than 5/5 condensed rings and 5/6 condensed rings, and can obtain better stability and safety performance. If the decomposition peak temperature of the compound 1 reaches 344 ℃, the friction sensitivity test limit value is more than 360N, the impact sensitivity is more than 40J, and the compound has excellent thermal stability and safety performance.
Although embodiments of the invention have been disclosed above, they are not limited to the use listed in the specification and embodiments. It can be applied to various fields suitable for the present invention. Additional modifications will readily occur to those skilled in the art. Therefore, the invention is not to be limited to the specific details and illustrations shown and described herein, without departing from the general concepts defined in the claims and their equivalents.
Claims (5)
1. A five-and seven-membered nitrogen heterocyclic compound, said energetic compound having the structure of formula (I):
2. a method of preparing the five-and seven-membered aza-fused ring compound of claim 1, comprising the steps of: adding 2-amino-4, 5-dicyanoimidazole into a solvent, adding guanidine into a reaction mixture for reaction, filtering after the reaction is finished, and recrystallizing to obtain a target compound shown as a formula (I).
3. The method of claim 2, wherein the molar ratio of 2-amino-4, 5-dicyanoimidazole to guanidine is 1:1.0 to 1:1.5.
4. The method of claim 2, wherein the reaction is carried out at a temperature of 60 to 85 ℃ for a time of 10 to 48 hours.
5. The method of claim 2, wherein the solvent is one of methanol, ethanol, acetone, and acetonitrile.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211252899.7A CN115557952B (en) | 2022-10-13 | 2022-10-13 | Five-membered and seven-membered nitrogen heterocyclic compound and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211252899.7A CN115557952B (en) | 2022-10-13 | 2022-10-13 | Five-membered and seven-membered nitrogen heterocyclic compound and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115557952A CN115557952A (en) | 2023-01-03 |
| CN115557952B true CN115557952B (en) | 2024-03-12 |
Family
ID=84744630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211252899.7A Active CN115557952B (en) | 2022-10-13 | 2022-10-13 | Five-membered and seven-membered nitrogen heterocyclic compound and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115557952B (en) |
-
2022
- 2022-10-13 CN CN202211252899.7A patent/CN115557952B/en active Active
Non-Patent Citations (2)
| Title |
|---|
| A study of the aromaticity and ring currents of azulene and azaazulenes;Rahila Mattohti;《RSC Adv.》;第6卷;fig.1中化合物45 * |
| Xie, Min.Synthesis, anticancer activity, and SAR analyses of compounds containing the 5:7-fused 4,6,8-triaminoimidazo[4,5-e][1,3]diazepine ring system.《Bioorganic & Medicinal Chemistry》.2016,第24卷(第12期),2597页化合物a，Scheme 5. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115557952A (en) | 2023-01-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9458115B2 (en) | Synthesis of substituted pyrazines | |
| CN114634462B (en) | Furazan-containing cyclonitrate simulated energetic compound or usable salt thereof and preparation method thereof | |
| CN115557952B (en) | Five-membered and seven-membered nitrogen heterocyclic compound and preparation method thereof | |
| SI9400003A (en) | Process for the preparation of biphenyl derivatives | |
| CN109705053B (en) | 2,2 '-dinitro-5, 5' -bis (1,3, 4-oxadiazole) and preparation method and application thereof | |
| WO2023151359A1 (en) | Tetrahydrocarbazole derivative as well as preparation method therefor and use thereof | |
| Zborovskii et al. | Heterocyclization reactions of 2-(2-propynylthio)-4 (1H)-quinazolinone derivatives when treated with electrophilic and nucleophilic reagents | |
| DE2508333A1 (en) | TRIAZOLO SQUARE BRACKET ON 4.3-ANGLE BRACKET FOR CHINAZOLINE | |
| Ranft et al. | New N1‐Hetarylmethylene‐Substituted Amidrazones with Potential Antimycobacterial Activity | |
| Shastin et al. | A new method for the synthesis of 2, 4-diazido-6-trinitromethyl-1, 3, 5-triazine | |
| CN115232149B (en) | Energetic compound with macrocyclic structure and preparation method thereof | |
| KR101529507B1 (en) | Di(aminoguanidium) 4,4',5,5'-tetranitro-2,2'-biimidazole, and preparation method thereof | |
| Abd-Elatif et al. | A General and a Simple Synthesis of {4-[(Z)-4-(Arylimino)-3, 4-Dihydroquinazolin-2 (1 H)-Ylidene] Cyclohexa-2, 5-Dien-1-Ylidene} Malononitrile from the Reaction of 2-Amino-N′-Arylbenzimidamides with 7, 7, 8, 8-Tetracyanoquinodimethane | |
| WO2004103282A2 (en) | Compounds, compositions and methods | |
| CN107383010A (en) | A kind of compound and preparation method thereof | |
| CN115368314A (en) | Nitro-imitation energetic compound containing oxadiazole ring and preparation method thereof | |
| US6476236B1 (en) | Synthesis of 2-cyanoaziridine-1-carboxamide | |
| CN117777145A (en) | Pyrazinopyridazine fused ring compounds and preparation method thereof | |
| US3644417A (en) | Coronary vasodilator compounds | |
| EP2327677A1 (en) | Mono-nitration of aromatic compounds | |
| Wang et al. | Synthesis and Characterization of BINOL Based Axially Chiral Nitronyl Nitroxide Radicals. | |
| Li et al. | A new convenient way to synthesize 1, 3, 4‐thiadiazol‐2‐yl urea derivatives under microwave irradiation | |
| CN116514785A (en) | Tetrazolyl-containing energetic compound and preparation method and application thereof | |
| JPH03215488A (en) | Pyrimidobenzimidazole derivative | |
| CN118084922A (en) | Inner salt type high heat-resistant explosive and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |