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Preparation method for flavonoid compounds

A technology of flavonoids and compounds, applied in the direction of organic chemistry, can solve the problems of unreported synthesis and achieve the effects of high reaction yield, simple operation and mild reaction conditions

Inactive Publication Date: 2011-04-13
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no report about applying Vilsmeier-Hacck to the synthesis of flavones

Method used

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  • Preparation method for flavonoid compounds
  • Preparation method for flavonoid compounds
  • Preparation method for flavonoid compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Embodiment 1: the preparation of flavone

[0026] Add 12.4mL of N,N-dimethylformamide (160mmol) and 10mL of 1,2-dichloroethane into a 100mL four-necked reaction flask equipped with a mechanical stirrer, a drying tube, a thermometer, and a dropping funnel. Stir and cool down to 0-5°C, then add bis(trichloromethyl)carbonate solution (11.9g, 40mmol, dissolved in 30mL 1,2-dichloroethane) dropwise, and react at 0-5°C after dropping 0.5 hours, then add 1-(2'-hydroxyphenyl)-3-phenyl-1,3-propanedione (4.8g, 20mmol) at 0-5°C The reaction was carried out at low temperature for 0.5 hours, and then the temperature was raised to 25-30° C. for 10 hours, and the progress of the reaction was tracked by TLC. After the reaction, pour the reaction mixture into 100mL ice water, stir for 1-1.5h, separate the organic layer, extract the water layer twice with 20mL×2 of 1,2-dichloroethane, combine the organic layers, and wash with 50mL saturated saline Wash once, dry over anhydrous sodium su...

Embodiment 2

[0028] Embodiment 2: the preparation of flavone

[0029]Add 6.2mL of N,N-dimethylformamide (80mmol) and 10mL of 1,2-dichloromethane into a 100mL four-necked reaction flask equipped with a mechanical stirrer, a drying tube, a thermometer, and a dropping funnel, and stir in an ice-water bath Cool down to 0-5°C, then add bis(trichloromethyl)carbonate solution (11.9g, 40mmol, dissolved in 30mL 1,2-dichloromethane) dropwise, and react at 0-5°C for 0.5 hour, and then added 1-(2'-hydroxyphenyl)-3-phenyl-1,3-propanedione (4.8g, 20mmol) at 0-5°C, and after the drop was completed, at 0-5°C React for 0.5 hours, then raise the temperature to 25-30° C. and react for 10 hours, and track the progress of the reaction by TLC. The separation and purification steps are the same as in Example 1 to obtain 4.0 g of flavonoids with a yield of 90%, and the physical property data are the same as in Example 1.

Embodiment 3

[0030] Embodiment 3: the preparation of flavone

[0031] Add 31.0mL N,N-dimethylformamide (400mmol) and 10mL 1,2-dichloromethane into a 100mL four-necked reaction flask equipped with a mechanical stirrer, a drying tube, a thermometer, and a dropping funnel, and stir to cool down in an ice-water bath to 0-5°C, then dropwise added bis(trichloromethyl)carbonate solution (23.7g, 80mmol, dissolved in 30mL 1,2-dichloromethane), and reacted at 0-5°C for 0.5 hours after dropping, Add 1-(2'-hydroxyphenyl)-3-phenyl-1,3-propanedione (4.8g, 20mmol) at 0-5°C, and react at 0-5°C for 0.5 hours, then the temperature was raised to 25-30° C. for 10 hours, and the progress of the reaction was tracked by TLC. The separation and purification steps are the same as in Example 1 to obtain 4.1 g of flavonoids with a yield of 91%, and the physical data are the same as in Example 1.

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Abstract

The invention provides a preparation method of flavonoids of formula (II), which comprises that adding bis (trichloromethyl) carbonate and N-N-dimethylformamide as raw materials into an organic solvent at 0-5 DEG C for reaction, adding 1-(2'-hydroxybenzene)-3-phenyl-1,3-propanedione compound of formula (I) at 0-5DEG C into the organic solvent to react for 0.5-2h, raising temperature to 25-30DEG C and reacting for 5-15h, separating and purifying the reaction liquid after the reaction to obtain the flavonoids of the formula (II), wherein the mass ratio between the 1-(2'-hydroxybenzene)-3-phenyl-1,3-propanedione compound, bis(trichloromethyl) carbonate and N-N-dimethylformamide is 1:2-4:4-20, and the organic solvent is a halohydrocarbon of C1-C4 or toluene. The invention has mild reaction condition, simple operation, high reaction yield and little pollution, which is a flavonoids chemical synthesis method with better application prospect.

Description

(1) Technical field [0001] The invention relates to a preparation method of flavonoids. (2) Background technology [0002] Flavonoids are a class of natural products that widely exist in the plant kingdom. It has a wide range of physiological activities, including anti-cardiovascular disease, anti-inflammatory, anti-hepatic virus, antibacterial and other activities. Flavonoids can be obtained directly from food, or extracted from plants rich in flavonoids, and used as food additives to make various health foods. The synthesis of flavonoids has received widespread attention from chemists. [0003] The research on the chemical synthesis of flavonoids has a long history, and there are two main routes for the classic synthesis methods, namely the chalcone route and the β-propanedione route. The β-propanedione route is that o-hydroxyacetophenone and aryl formyl chloride (or aryl formic acid or aryl formic anhydride) first form an ester, then intramolecular Claisen rearrangemen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/30
Inventor 苏为科李振华朱兴一
Owner ZHEJIANG UNIV OF TECH