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Mechanochemical preparation of flavonoid

A technology of flavonoids and mechanochemistry, applied in the direction of organic chemistry, can solve problems in the research and exploration stage, and achieve the effects of shortening reaction time, low production cost and high yield

Inactive Publication Date: 2009-05-27
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, some people have adopted I 2 -DMSO, Co III (salpr)(OH) or trifluoromethanesulfonic acid to synthesize flavonoids, and some people use CuCl 2 or [EtNH 3 ]NO 3 Microwave-assisted synthesis of flavonoids, but these methods are still in the research and exploration stage
Also do not see the report that adopts mechanochemical method to prepare flavonoids at present

Method used

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  • Mechanochemical preparation of flavonoid
  • Mechanochemical preparation of flavonoid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the preparation of flavone

[0024] Add 1-(2′-hydroxyphenyl)-3-phenyl-1,3-propanedione (2.40 g, 10 mmol), potassium bisulfate (0.07 g, 0.5 mmol) and silica gel (12 g ), then add grinding balls, and tighten the jar lid. The ball mill jar was put into a ball mill and operated at a rotational speed of 1290 rpm to allow the mixture to react for 5 minutes, and TLC (sample was dissolved in DMF) was used to track the progress of the reaction. After the reaction, the reaction mixture was washed with hot absolute ethanol and filtered. The filtrate was boiled to evaporate part of the ethanol to saturation, cooled to room temperature, and the solid was precipitated and dried to obtain 2.02 g of flavones with a yield of 90%.

[0025] White solid, mp: 96-97°C. 1 H NMR (400MHz, CDCl3): δ=8.24(d, J=8.0Hz, 1H, ArH), 7.94(d, J=8.0Hz, 2H, ArH), 7.71(t, J=8.0Hz, 1H, ArH ), 7.53-7.60 (m, 4H, ArH), 7.43 (t, J=8.0Hz, 1H, ArH), 6.86 (s, 1H, CH). 13 C NMR (100MHz, CDCl 3 ): ...

Embodiment 2

[0026] Embodiment 2: the preparation of flavone

[0027] Add 1-(2'-hydroxyphenyl)-3-phenyl-1,3-propanedione (2.40g, 10mmol), potassium hydrogensulfate (0.14g, 1mmol) and silica gel (12g) into a 75mL ball mill jar , then add the grinding balls, and tighten the jar lid. The ball mill jar was put into a ball mill and operated at a rotational speed of 1290 rpm to allow the mixture to react for 5 minutes, and TLC (sample was dissolved in DMF) was used to track the progress of the reaction. The separation and purification steps are the same as in Example 1 to obtain 2.04 g of flavonoids with a yield of 91%, and the physical data are the same as in Example 1.

Embodiment 3

[0028] Embodiment 3: the preparation of flavone

[0029] Add 1-(2'-hydroxyphenyl)-3-phenyl-1,3-propanedione (2.40g, 10mmol), potassium hydrogensulfate (0.27g, 2mmol) and silica gel (24g) into a 75mL ball mill jar , then add the grinding balls, and tighten the jar lid. The ball mill jar was put into a ball mill and operated at a rotational speed of 1290 rpm to allow the mixture to react for 5 minutes, and TLC (sample was dissolved in DMF) was used to track the progress of the reaction. The separation and purification steps are the same as in Example 1 to obtain 2.09 g of flavonoids with a yield of 93%, and the physical property data are the same as in Example 1.

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Abstract

The invention discloses a mechanochemical preparation method for flavone compounds with a structure shown in a formula (II), which comprises the following steps: 1-(2'-hydroxy phenyl)-3-aryl-1, 3-propanedione with a structure shown in a formula (I) is taken as a raw material, hydrosulfate is taken as a catalyst, and silica gel is taken as a grinding aid to perform a ball grinding reaction in a closed ball grinding tank; and after the reaction is finished, a reaction mixture is separated and purified to obtain the flavone compounds with the structure shown in the formula (II). The method has the advantages of short reaction time, generally higher reaction yield, safe and reliable production, low production cost, simple post-treatment, small pollution and so on, and is the preparation method for the flavone compounds with better popularization and application prospects.

Description

(1) Technical field [0001] The invention relates to a mechanochemical preparation method of flavonoids. (2) Background technology [0002] Flavonoids are an important class of natural products, which have various activities such as anti-cardiovascular disease, anti-inflammation, anti-hepatic virus, and antibacterial. 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 rearrangement to generate a β-propanedione intermediate, and fi...

Claims

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Application Information

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IPC IPC(8): C07D311/30
Inventor 李振华朱兴一苏为科舒强锋周陈锋
Owner ZHEJIANG UNIV OF TECH
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