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Synthesis method of furoxan compound

A technology of furoxan and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of dangerous reagents, multiple reactions, and large pollution, and achieve the effects of green and environmental protection, mild reaction conditions, and simple post-treatment

Active Publication Date: 2020-12-25
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Claims
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Problems solved by technology

In the method of designing furoxan ring, some reports reported that the synthesis is under the participation of organic base, catalyzing the action of sulfonyl chloride and nitroxime group to realize the ring-forming function of dehydrodehydration, but due to the high activity of acid chloride The conditions of this type of synthesis method are relatively harsh, and the participation of more active acid chlorides makes certain requirements for substituents, which makes it unfavorable for the synthesis design of the structure of furoxan oxide containing energy; in addition, some use copper perchlorate Participate in the ring-closing reaction process as a dehydrogenation material, such as: Das O, Paria S, Paine TK. Copper(II)-mediated oxidation of 1,2-dioxime to furoxan[J].TetrahedronLetters,2008,49(41):5924 -The synthetic method disclosed in 5927; some use bromine water and chlorine water as oxidants to achieve the purpose of ring closure, such as Fischer, D., et al. (2014). "Synthesis and Characterization of Diaminobisfuroxane." European Journal of Inorganic Chemistry 2014( 34): the synthetic method disclosed in 5808-5811; some research scholars use lead peroxide or concentrated nitric acid mixed acid to participate in this type of reaction, but when these chemical reactions are carried out, there are large pollution, cumbersome post-treatment process, and dangerous reaction reagents. , Oxidants are volatile and have many side reactions or reaction limitations

Method used

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  • Synthesis method of furoxan compound
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  • Synthesis method of furoxan compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The synthesis of 3-cyano-4-aminofuroxan, the structural formula of 3-cyano-4-aminofuroxan is as follows:

[0039]

[0040] The reaction mechanism is:

[0041]

[0042] The synthetic method comprises the steps:

[0043] Take a 250mL three-neck flask, put it into a magnetic stirrer, weigh and add 1-amino-2-cyanoglyoxime (5.12g, 0.04mol), place the reactor in a water bath to maintain the reaction system at 30°C, and then add 120 mL of anhydrous acetonitrile solvent, finally added iodobenzenediethyl ester (12.88 g, 0.04 mol) in batches, and the reaction was stirred at room temperature for 2 h. After the reaction, the organic solvent was removed with a rotary evaporator, washed with ice water, filtered and dried to obtain 3.01 g of white-yellow pure furazan oxide solid particles with a yield of 60%. 1 H NMR (400MHz, DMSO) δ7.10; 13 C NMR (101 MHz, DMSO) δ 156.16, 107.14, 93.48. Anal calcd for C 3 h 2 o 2 N 2 : C28.57, H1.587, N44.44; Found C28.84, H1.75, N44.91...

Embodiment 2

[0046] Synthesis of 3,4-diphenylfuroxan, the structural formula of 3,4-diphenylfuroxan is as follows:

[0047]

[0048] The synthetic route is:

[0049]

[0050] The synthetic method comprises the steps:

[0051] Take a 100mL three-neck flask, put it into a magnetic stirrer, weigh and add benzildioxime (0.24g, 1mmol), place the reactor in a water bath to maintain the reaction system at 30°C, and then add 30mL of absolute ethanol solvent, The stirring system was milky white, and finally iodobenzenediethyl ester (0.322 g, 1 mmol) was added in batches several times, and the solution quickly turned into a yellow-green clear system, and the reaction was stirred at room temperature for 2 h. After the reaction, use a rotary evaporator to remove absolute ethanol, add ice water to wash and extract with ethyl acetate, separate and retain the organic phase, dry and filter with anhydrous sodium sulfate, continue to remove ethyl acetate by vacuum rotary evaporation, and vacuum dry Af...

Embodiment 3

[0054] The synthesis of cyclohexane and furoxan oxide, the structural formula of cyclohexane and furoxan oxide is as follows:

[0055]

[0056] The synthetic route is:

[0057]

[0058] The synthetic method comprises the steps:

[0059] Take a 250mL three-neck flask, put it into a magnetic stirrer, weigh and add 1,2-cyclohexanedionedioxime (0.142g, 1mmol), place the reactor in a water bath to keep the reaction system at 30°C, and then add 30mL of Water and acetonitrile were used as a solvent, and finally iodobenzenediethyl ester (0.322 g, 1 mmol) was added in batches, and the reaction was stirred at room temperature for 2 h. After the reaction was monitored by thin-layer chromatography, the organic solvent was removed with a rotary evaporator, washed with ice water and extracted with ethyl acetate for multiple times to separate the layers. The solvent was removed by rotary evaporation, and finally vacuum-dried to obtain 0.115 g of a yellow pure furoxan oily product wit...

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Abstract

The invention discloses a synthesis method of a furazan oxide compound. The synthesis method comprises the following step of: oxidizing a glyoxime compound by taking iodobenzene diethyl ester as an oxidizing agent to carry out a reaction to obtain the furazan oxide compound. No heavy metal, acid or alkali participates in the reaction process. The method 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 a certain industrial value; besides, the reaction raw materials do not contain acyl chloride compounds with higher activity, no strict requirements are imposed on substituent groups of the furoxan compound, so that a new synthesis path is opened up for the furoxan compound containing groups which are easy to react with the acyl chloride compounds.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a method for synthesizing furoxan compounds applicable to the fields of energetic chemistry and medicine. Background technique [0002] Oxyfuroxan compound is a nitrogen-oxygen five-membered heterocyclic compound containing active coordinating oxygen. Because of its special structure and performance, it has a wide range of applications in the field of medicine and energetic chemistry. Studies have shown that the substitution of drug molecules or other heterocyclic molecules on the carbon atom of furoxan ring can release NO under the induction of thiol factors. Furazan oxide, as a NO donor, affects physiological and pathological processes. High concentrations of nitric oxide can induce apoptosis and lead to tumor cell death, while low concentrations of nitric oxide can cause vasodilation and anticoagulation, such as 3-cyano-4-phenylfuroxan can be used for Chemotherapy f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/08C07D271/12
CPCC07D271/08C07D271/12
Inventor 何春林赵铖尹平庞思平窦辉陈鹏
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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