CN112125865A - Synthesis method of furoxan compound - Google Patents

Synthesis method of furoxan compound Download PDF

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CN112125865A
CN112125865A CN202011059071.0A CN202011059071A CN112125865A CN 112125865 A CN112125865 A CN 112125865A CN 202011059071 A CN202011059071 A CN 202011059071A CN 112125865 A CN112125865 A CN 112125865A
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furoxan
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furoxan compound
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CN112125865B (en
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何春林
赵铖
尹平
庞思平
窦辉
陈鹏
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Beijing Institute of Technology BIT
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
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    • C07—ORGANIC CHEMISTRY
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    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
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Abstract

The invention discloses a synthesis method of a furazan oxide compound, which comprises the following steps: and oxidizing the glyoxime compound by using diethyl iodobenzene as an oxidant to obtain a furazan oxide compound. The method has no heavy metal and acid-base participating reaction process, has the advantages of mild reaction conditions, high efficiency, green and environment-friendly process, simple post-treatment and the like, and is a synthetic method with certain industrial value; in addition, the reaction raw materials do not have acyl chloride compounds with high activity, the strict requirement on the substituent group of the furoxan compound is not required, and a new synthesis path is opened up for the furoxan compound containing a group which is easy to react with the acyl chloride compounds.

Description

Synthesis method of furoxan compound
Technical Field
The invention relates to the technical field of organic chemistry, in particular to a synthetic method of a furazan oxide compound, which can be applied to the fields of energetic chemistry and medicine.
Background
The furoxan compound is a compound containingThe nitrogen-oxygen five-membered heterocyclic compound of active coordinated oxygen has wide application in the fields of medicine and energetic chemistry due to the particularity of the structure and the performance. Research shows that, the substitution of drug molecules or other heterocyclic molecules on the carbon atom of the furazan ring can release NO under the induction of thiol factors, the furazan as a NO donor affects physiological and pathological processes, high concentration of nitric oxide can induce apoptosis to cause tumor cell death, and low concentration of nitric oxide can cause vasodilation and anticoagulation, etc., for example, 3-cyano-4-phenyl furazan can be used for the chemotherapy of hematuria disease. In addition, in the field of energetically-containing chemistry, which is excellent as a high-energy backbone group, such as 3-cyano-4-aminofuroxan, which is an intermediate precursor compound frequently used in designing high-energy compounds, on the basis of which an excellent energetic compound, 3, 4-bis (3-nitrofuroxan-4-yl) furoxan (1.91 g/cm) can be synthesized39503m/s), while the direct 3, 4-dinitrofurazanyl furoxan (DNTF) is also an energetic material of high energy density.
The existing main means for synthesizing the furoxan structure comprises the following steps: dimerization of cyano nitroxides, condensation of alpha-nitro (halogen, amino) oximes, deaza gas ring closure of alpha-nitro azides and dehydrooxidation of bis-oximino groups. In the method for designing the furoxan ring, in some reports, the synthesis is to catalyze sulfonyl chloride to react with a nitrooximino group in the presence of organic base to realize the ring formation function of dehydrogenation and dehydration, but the acyl chloride has high activity, so that the conditions of the synthesis method are severe, and meanwhile, the acyl chloride with high activity has certain requirements on substituent groups, so that the synthesis method is not favorable for the synthesis design of the energy-containing furoxan structure; in addition, some copper perchlorate salts are adopted as dehydrogenation materials to participate in the ring closing reaction process, such as: (iii) the synthetic method disclosed in Das O, Paria S, Paine T K. Copper (II) -mediated oxidation of 1,2-dioxime to furoxan [ J ]. Tetrahedron Letters,2008,49(41): 5924-); some methods for using bromine water and chlorine water as oxidants to achieve the ring closing purpose, such as the Synthesis method disclosed in Fischer, D., et al (2014), "Synthesis and chromatography of Diambis fuel." European Journal of organic Chemistry 2014(34): 5808-; lead peroxide or concentrated nitric-sulfuric mixed acid is adopted by other researchers to participate in the reactions, but the chemical reactions have the characteristics of high pollution, complex post-treatment process, dangerous reaction reagents, easy volatilization of oxidants, more side reactions or reaction limitation and the like. Aiming at the defects of the synthetic furoxan compound and the purpose of structural design of the furoxan compound containing a functional group, under the requirements of industrial greenization, high efficiency, economy and the like, the green and environment-friendly mild method for synthesizing the furoxan is necessary.
Disclosure of Invention
An object of the present invention is to solve at least the above problems and/or disadvantages and to provide at least the advantages described hereinafter.
The invention also aims to provide a synthesis method of the furoxan compound, which has no heavy metal and acid-base participating in the reaction process, has the advantages of mild reaction conditions, high efficiency, green and environment-friendly process, simple post-treatment and the like, and has certain industrial value; in addition, the reaction raw materials do not have acyl chloride compounds with high activity, the strict requirement on the substituent group of the furoxan compound is not required, and a new synthesis path is opened up for the furoxan compound containing a group which is easy to react with the acyl chloride compounds.
To achieve these objects and other advantages in accordance with the purpose of the present invention, there is provided a synthesis method of a furoxan compound, in which diethyliodobenzene is used as an oxidizing agent.
Preferably, wherein the diethyliodobenzene is used to oxidize the glyoxime compound.
Preferably, wherein the furoxan compound has the structure as in formula (I) below:
Figure BDA0002711795360000021
wherein R is1Is one of amino, aryl and alkyl, R2Is one of hydrogen, cyano, aryl and alkyl.
Preferably, wherein the glyoxime compound has the structure as in the following formula (I):
Figure BDA0002711795360000031
preferably, the method for synthesizing the furoxan compound comprises the following steps:
dissolving the glyoxime compound in an organic solvent, placing the solution in a water bath to keep a reaction system at 30 ℃, adding the diethyl iodobenzene oxidant in batches to react, decompressing after the reaction is finished, removing the organic solvent, and purifying to obtain the furoxan compound.
Preferably, the organic solvent is one of anhydrous acetonitrile, anhydrous ethanol, anhydrous dichloromethane and anhydrous methanol.
Preferably, the reaction temperature is 25 to 30 ℃.
Preferably, the molar ratio of the compound in the formula (II) to the dehydrogenation oxidizing agent is 1:1-1: 1.5.
Preferably, the reaction time is 1-2 h.
Preferably, wherein the purification treatment comprises: washing with ice water, filtering and drying.
The invention at least comprises the following beneficial effects:
1. the synthesis method disclosed by the invention has no heavy metal and acid-base participating in the reaction process, has the advantages of mild reaction conditions, high efficiency, green and environment-friendly process, simple post-treatment and the like, and has a certain industrial value;
2. the reaction raw materials of the invention do not contain acyl chloride compounds with larger activity, have no strict requirements on the substituent group of the furoxan compound, and open up a new synthetic path for the furoxan compound containing groups which are easy to react with the acyl chloride compounds.
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 hydrogen spectrum of nuclear magnetic resonance of 3-cyano-4-aminofuroxan synthesized in example 1 of the present invention;
FIG. 2 is a carbon spectrum diagram of nuclear magnetic resonance of 3-cyano-4-aminofuroxan synthesized in example 1 of the present invention;
FIG. 3 is a hydrogen spectrum of nuclear magnetic resonance of 3, 4-diphenylfuroxan synthesized in example 2 of the present invention;
FIG. 4 is a carbon spectrum of nuclear magnetic resonance of 3, 4-diphenylfuroxan synthesized in example 2 of the present invention;
FIG. 5 is a hydrogen spectrum by nuclear magnetic resonance of cyclohexanonofuroxan synthesized in example 3 of the present invention;
FIG. 6 is a carbon spectrum by nuclear magnetic resonance of cyclohexanonofuroxan synthesized in example 3 of the present invention;
FIG. 7 is a NMR hydrogen spectrum of 1,2, 5-oxadiazole-2-oxide synthesized in example 4 of the invention;
FIG. 8 is a carbon spectrum of nuclear magnetic resonance of 1,2, 5-oxadiazole-2-oxide synthesized in example 4 of the present invention.
Detailed Description
The present invention is further described in detail below with reference to the attached drawings so that those skilled in the art can implement the invention by referring to the description text.
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.
It is to be noted that the experimental methods described in the following embodiments are all conventional methods unless otherwise specified, and the reagents and materials are commercially available unless otherwise specified.
The general reaction formula of the invention is:
Figure BDA0002711795360000041
< example 1>
The synthesis of 3-cyano-4-aminofuroxan, the structural formula of 3-cyano-4-aminofuroxan is as follows:
Figure BDA0002711795360000042
the reaction mechanism is as follows:
Figure BDA0002711795360000051
the synthesis method comprises the following steps:
a250 mL three-neck flask is taken and put into a magnetic stirrer, 1-amino-2-cyanoglyoxime (5.12g, 0.04mol) is weighed and added, the reactor is placed into a water bath to keep a reaction system at 30 ℃, 120mL of anhydrous acetonitrile solvent is added, finally, diethyl iodobenzene (12.88g,0.04mol) is added in batches for multiple times, and the reaction is stirred and reacted for 2 hours at room temperature. After the reaction is finished, the organic solvent is removed by a rotary evaporator, and the white and yellow pure furoxan solid particle product is obtained by washing, filtering and drying with ice water, wherein the yield is 60 percent.1H NMR(400MHz,DMSO)7.10；13C NMR(101MHz,DMSO)156.16,107.14,93.48。Anal calcd for C3H2O2N2:C28.57,H1.587,N44.44；Found C28.84,H1.75,N44.91。
Wherein the NMR spectrum is shown in figure 1, and the NMR spectrum is shown in figure 2.
< example 2>
The synthesis of 3, 4-diphenyl furoxan, the structural formula of 3, 4-diphenyl furoxan is as follows:
Figure BDA0002711795360000052
the synthetic route is as follows:
Figure BDA0002711795360000053
the synthesis method comprises the following steps:
taking a 100mL three-neck flask, putting a magnetic stirrer, weighing and adding benzil dioxime (0.24g, 1mmol), placing the reactor in a water bath to keep a reaction system at 30 ℃, adding 30mL of absolute ethanol solvent, stirring the system to be milk white, adding diethyl iodobenzene (0.322g, 1mmol) in batches for multiple times, quickly changing the solution into a yellow-green clear system, and stirring and reacting for 2 hours at room temperature. After the reaction is finished, absolute ethyl alcohol is removed by using a rotary evaporator, ice water is added for washing, ethyl acetate is used for extraction, liquid separation is carried out to keep an organic phase, anhydrous sodium sulfate is dried and filtered, ethyl acetate is continuously removed through reduced pressure rotary evaporation, and vacuum drying is carried out to realize purification, so that 0.204g of yellow pure furazan oxide solid product can be obtained, and the yield is 86.0%.1H NMR(400MHz,CDCl3)7.51,7.46；13C NMR(101MHz,CDCl3)156.24,130.56,130.18,129.04,128.97,128.70,128.30,126.67,122.88。Anal calcd for C14H10O2N2:C70.58,H4.23,N11.76。Found C70.1,H4.3,N11.5。
Wherein the NMR spectrum is shown in FIG. 3, and the NMR spectrum is shown in FIG. 4.
< example 3>
The synthesis of the cyclohexanonofuroxan has the following structural formula:
Figure BDA0002711795360000061
the synthetic route is as follows:
Figure BDA0002711795360000062
the synthesis method comprises the following steps:
adding a magnetic stirrer into a 250mL three-neck flask, weighing and adding 1, 2-cyclohexanedione dioxime (0.142g, 1mmol), placing the reactor in a water bath to keep a reaction system at 30 ℃, adding 30mL of anhydrous acetonitrile solvent, and finally adding iodobenzene diethyl ether for multiple times in batchesEster (0.322g, 1mmol) and the reaction stirred at room temperature for 2 h. After the thin-layer chromatography monitoring reaction is finished, removing the organic solvent by using a rotary evaporator, washing by using ice water, extracting and layering by using ethyl acetate for multiple times, retaining an organic phase after liquid separation, drying by using anhydrous sodium sulfate to remove residual water, carrying out reduced pressure rotary evaporation to remove the solvent, and finally carrying out vacuum drying to obtain 0.115g of a yellow pure furazan oxide oily product, wherein the yield is 88.7%.1H NMR(400MHz,CDCl3)2.79,2.59；13C NMR(101MHz,CDCl3)156.07,113.02,22.11,21.27,21.05,19.42。Anal calcd for C6H8O2N2:C51.43,H5.71,N20.00。Found C50.84,H5.62,N20.46。
Wherein the NMR spectrum is shown in FIG. 5, and the NMR spectrum is shown in FIG. 6.
< example 4>
Synthesis of 1,2, 5-oxadiazole-2-oxide, the structural formula of 1,2, 5-oxadiazole-2-oxide is as follows:
Figure BDA0002711795360000063
the synthetic route is as follows:
Figure BDA0002711795360000064
the synthesis method comprises the following steps:
a magnetic stirrer is placed in a 100mL three-neck flask, glyoxime (0.176g and 2mmol) is weighed and added, the reactor is placed in a water bath to keep a reaction system at 30 ℃, 50mL dichloromethane solvent is added, the stirring system is milky, then iodobenzene diethyl ester (0.644g and 2mmol) is added, the solution gradually becomes brown yellow, and the stirring reaction is continued for 2 hours. After the reaction is finished, filtering and rotary steaming are carried out to remove dichloromethane, ice water is added for washing, ethyl acetate is used for extraction, liquid separation and organic phase retention are carried out, anhydrous sodium sulfate is dried and filtered, decompression and rotary steaming are carried out continuously to remove ethyl acetate, vacuum drying is carried out, 0.146g of yellow oily product can be obtained, and the yield is 85.0%.1H NMR(400MHz,CDCl3)7.71,7.10.13C NMR(101MHz,CDCl3)137.46,127.44。
Wherein the NMR spectrum is shown in FIG. 7, and the NMR spectrum is shown in FIG. 8.
In conclusion, the synthesis method disclosed by the invention has the advantages that no heavy metal or acid and alkali participate in the reaction process, the reaction condition is mild, the efficiency is high, the process is green and environment-friendly, and the post-treatment is simple; the raw materials of the reaction have no acyl chloride compounds with larger activity, the strict requirement on the substituent group of the furoxan compound is not required, the yield is equivalent to that of a synthetic route in which sulfonyl chloride and organic base participate in the reaction, and a new synthetic path is opened up for the furoxan compound containing a group which is easy to react with the acyl chloride compounds.
While embodiments of the invention have been disclosed above, it is not intended to be limited to the uses set forth in the specification and examples. It can be applied to all kinds of fields suitable for the present invention. Additional modifications will readily occur to those skilled in the art. It is therefore intended that the invention not be limited to the exact details and illustrations described and illustrated herein, but fall within the scope of the appended claims and equivalents thereof.

Claims (10)

1. A synthetic method of a furoxan compound is disclosed, wherein diethyliodobenzene is used as an oxidant.
2. A synthesis method of a furoxan compound as claimed in claim 1, wherein the diethyliodobenzene is used to oxidize a glyoxime compound.
3. A method of synthesis of a furoxan compound as claimed in claim 1 wherein the furoxan compound has the structure as in formula (I):
Figure FDA0002711795350000011
wherein R is1Is one of amino, aryl and alkyl, R2Is one of hydrogen, cyano, aryl and alkyl.
4. A method of synthesis of a furoxan compound as claimed in claim 1 wherein the glyoxime compound has the structure as in formula (I):
Figure FDA0002711795350000012
5. a method of synthesis of a furoxan compound as claimed in claim 2, wherein the method of synthesis of a furoxan compound comprises the steps of:
dissolving the glyoxime compound in an organic solvent, placing the solution in a water bath to keep a reaction system at 30 ℃, adding the diethyl iodobenzene oxidant in batches to react, decompressing after the reaction is finished, removing the organic solvent, and purifying to obtain the furoxan compound.
6. A synthesis method of a furazan oxide compound according to claim 1, wherein the organic solvent is one of anhydrous acetonitrile, anhydrous ethanol, anhydrous dichloromethane and anhydrous methanol.
7. A synthesis method of a furoxan compound as claimed in claim 1, wherein the reaction temperature is 25-30 ℃.
8. A process for the synthesis of a furoxan compound as claimed in claim 1, wherein the molar ratio of the compound of formula (II) to dehydrooxidative reagent is from 1:1 to 1: 1.5.
9. A synthesis method of a furoxan compound as claimed in claim 1, wherein the reaction time is 1-2 h.
10. A method of synthesising a furoxan compound as claimed in claim 1 wherein the purification treatment comprises: washing with ice water, filtering and drying.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114634462A (en) * 2022-04-15 2022-06-17 北京理工大学 Nitro-imitation energetic compound containing furoxan ring or available salt thereof and preparation method thereof

Citations (1)

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Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
CN1119013A (en) * 1993-03-06 1996-03-20 赫彻斯特股份公司 Hydroxymethyl furazane carboxylic acid derivatives and their use in the treatment of cardio-vascular conditions

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Title
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OM PRAKASH ET AL: "Hypervalent iodine oxidation of 1-phenyl-3-arylpyrazole-4-carboxaldehyde oximes: a facile and efficient synthesis of new 3,4-bis(1-phenyl-3-arylpyrazolyl)-1,2,5-oxadiazole-N-oxides", 《ARKIVOC》 *
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114634462A (en) * 2022-04-15 2022-06-17 北京理工大学 Nitro-imitation energetic compound containing furoxan ring or available salt thereof and preparation method thereof
CN114634462B (en) * 2022-04-15 2023-09-29 北京理工大学 Furazan-containing cyclonitrate simulated energetic compound or usable salt thereof and preparation method thereof

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