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Alpha-azidocarbonyl compounds and preparation method thereof

A technology for azidocarbonyl compounds, which is applied in the field of organic compound synthesis, can solve problems such as insufficiently mild reaction conditions and complicated operation of α-azidocarbonyl compounds, and achieve the effects of simple operation, simple post-treatment, and high reaction efficiency

Inactive Publication Date: 2017-08-18
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The first technical problem to be solved by the present invention is the problem of complex operation in the preparation process of α-azidocarbonyl compounds
[0014] The second technical problem to be solved by the present invention is the problem that the reaction conditions are not mild enough in the preparation process of α-azidocarbonyl compounds
[0015] The third technical problem to be solved by the present invention is to make the preparation process of α-azidocarbonyl compound suitable for large-scale industrial production

Method used

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  • Alpha-azidocarbonyl compounds and preparation method thereof
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  • Alpha-azidocarbonyl compounds and preparation method thereof

Examples

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preparation example Construction

[0067] In the preparation method of the present invention, the reaction temperature is -80-40°C, non-limitingly, for example, -80°C, -40°C, -20°C, -10°C, 0°C, 10°C or 40°C

[0068] (6) Response time

[0069] In the preparation method of the present invention, the reaction time is not particularly limited. For example, the appropriate reaction time can be determined by detecting the residual percentage of the target product or raw material by liquid chromatography, which is usually 0.5-30 hours, non-limitingly for example 1 hour, 4 hours, 6 hours, 8 hours, 10 hours, 12 hours, 14 hours, 26 hours, 28 hours or 30 hours.

[0070] (7) Separation and purification

[0071] The mixture obtained after the reaction can be further separated and purified to obtain a purer final product. Those of ordinary skill in the art are familiar with the methods of separation and purification, for example, methods such as extraction, column chromatography, distillation, decantation, filtration, cent...

Embodiment 1

[0075] Synthesis of 2-Azide-Acetophenone

[0076]

[0077] At room temperature, copper acetate (5mol%) and potassium persulfate (0.8mmol, 2equiv) were added to the reaction tube, then pumped-oxygenated, and replaced three times, under an oxygen environment, the reaction solvent 2mLDMSO, phenylacetylene ( 0.4mmol, 1equiv), trimethylsilyl azide (1.2mmol, 3equiv), stirred at a reaction temperature of 25°C for 12h; after the reaction was monitored by thin-layer chromatography, 20mL of water and 10mL of ethyl acetate were added for extraction operation, and then added Dry over anhydrous sodium sulfate, filter after 5 minutes, wash the filter cake with ethyl acetate (5mL x 3 times), then spin off the solvent, and obtain the product after separation by column chromatography (elution machine: petroleum ether: diethyl ether=100: 1), the product is a colorless liquid with a yield of 91%;

[0078] The data of the proton nuclear magnetic resonance spectrum of gained product are as fol...

Embodiment 2

[0086] Synthesis of 2-Azido-1-(4-Hydroxyphenyl)ethanone

[0087]

[0088] At room temperature, copper acetate (5mol%), potassium persulfate (0.8mmol, 2equiv) were added to the reaction tube, then pump-filled with oxygen, and replaced three times, under oxygen environment, the reaction solvent 2mLDMSO, 4-hydroxy Phenylacetylene (0.4mmol, 1equiv), trimethylsilyl azide (1.2mmol, 3equiv), stirred at a reaction temperature of 25°C for 12h; after the completion of the reaction was monitored by thin-layer chromatography, 20mL of water and 10mL of ethyl acetate were added for extraction operation , then add anhydrous sodium sulfate to dry, filter after 5 minutes, the filter cake is washed with ethyl acetate (5mL x 3 times), then spin off the solvent, obtain the product after separation by column chromatography (elution machine: petroleum ether: diethyl ether =100:5), the product is a white solid, and the yield is 89%;

[0089] The data of the proton nuclear magnetic resonance spec...

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Abstract

The invention relates to alpha-azidocarbonyl compounds and a preparation method thereof. The method comprises the step of carrying out alkyne difunctionalization reaction on terminal alkynes and azidotrimethylsilane used as reaction raw materials in an organic solvent under the acceleration actions of a copper catalyst and a persulfate oxidizer, thereby obtaining the alpha-azidocarbonyl compounds. In the azido free radical oxidizing process, air is used as the terminal oxidizer to perform a key function in the reaction process. The method has the advantages of wide substrate range, ambient operation, mild reaction conditions, simple after-treatment, and high product yield and purity, provides a new synthesis route and method for alpha-azidocarbonyl compounds, and thus, has great application potential and research value.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to an α-azidocarbonyl compound and a preparation method. Background technique [0002] α-Azidocarbonylation is often used as a useful intermediate in the synthesis of heterocyclic compounds such as oxazole, pyrazole, imidazole and pyrrole and other nitrogen-containing heterocyclic compounds; Alkanes, β-amino alcohol compounds and amino acid derivatives. In recent years, copper-catalyzed "click chemistry" of azides and alkynes has been used to synthesize a series of functionalized 1,2,3-triazole compounds. [0003] [0004] α-Azidocarbonyl compounds as key intermediates [0005] Although this type of compound has a wide range of uses, its preparation method is less reported, mainly using the nucleophilic substitution reaction of carbonyl α-halogen compound and sodium azide. [0006] In 2000, Lee et al. reported that organic ketone compounds and HNIB (hydroxyl...

Claims

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Application Information

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IPC IPC(8): C07C247/10C07D295/112C07D333/22C07C247/04C07D231/12C07D409/04
CPCC07C247/10C07C247/04C07D231/12C07D295/112C07D333/22C07D409/04
Inventor 吴戈
Owner WENZHOU MEDICAL UNIV
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