Chemical synthesis method of flavonoid compound

A technology of chemical synthesis of flavonoids, which is applied in the field of chemical synthesis of flavonoids, can solve the problems of being in the research and exploration stage, difficult to recycle, and environmental pollution, and achieve the effects of environmental friendliness, no three wastes, and reasonable process routes

Inactive Publication Date: 2009-10-14
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Wherein the cyclization reaction generally uses acid catalysts such as sulfuric acid and hydrochloric acid before the method of the present invention, and the use of these acids has not only corroded equipment, is difficult to recycle and apply mechanically, but also pollutes the environment
Although in recent years some people have used I 2 -DMSO, Co III (salpr)(OH) or microwave assisted (addition of CuCl 2 or [EtNH 3 ]NO 3 ) and other methods to synthesize flavonoids, but these methods are still in the research and exploration stage

Method used

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  • Chemical synthesis method of flavonoid compound
  • Chemical synthesis method of flavonoid compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the preparation of flavone

[0024] Add 50mL of nitromethane 1-(2'-hydroxyphenyl)-3-phenyl-1,3-propanedione into a 100mL four-necked reaction flask equipped with mechanical stirring, drying tube, thermometer and dropping funnel (4.8g, 20mmol) and gallium trifluoromethanesulfonate (516mg, 1mmol), the temperature was raised to 80°C for 2 hours, and the progress of the reaction was tracked by TLC. After the reaction, the reaction mixture was poured into 100 mL of water, extracted three times with 20 mL of dichloromethane × 3, the organic layers were combined, dried over anhydrous sodium sulfate, the solvent was removed by rotary evaporation, and then recrystallized with ethanol to obtain 4.28 g of flavonoids, white Solid, melting point 96-97°C, yield 96.4%. The aqueous phase was concentrated under reduced pressure to obtain white crystals, which were heated to 200°C under vacuum to obtain white crystals (Ga(OTf) 3 ) 475 mg, 92%.

Embodiment 2

[0025] Embodiment 2: the preparation of flavone

[0026] Nitromethane 50 mL, 1-(2'-hydroxyphenyl)-3-phenyl-1,3-propanedione (4.8 g, 20 mmol), bismuth trifluoromethanesulfonate (656 mg, 1 mmol). Other operations are the same as in Example 1. 4.19 g of flavonoids were obtained with a yield of 94.4%. 590.4 mg of bismuth trifluoromethanesulfonate was recovered, and the yield was 90%.

Embodiment 3

[0027] Embodiment 3: the preparation of flavone

[0028] Nitromethane 50 mL, 1-(2'-hydroxyphenyl)-3-phenyl-1,3-propanedione (4.8 g, 20 mmol), copper trifluoromethanesulfonate (362 mg, 1 mmol). Other operations are the same as in Example 1. 4.01 g of flavonoids were obtained with a yield of 90.3%. 307.5 mg of copper trifluoromethanesulfonate was recovered, and the yield was 84.9%.

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Abstract

The invention discloses a chemical synthesis method of a flavonoid compound shown by a formula (II). The synthesis method comprises the following steps : under the catalysis of trifluoromethanesulfonic salt, a beta-propanedione derivant shown by a formula (I) fully reacts in an organic solvent under temperature of 0 DEG C to 100 DEG C, and the flavonoid compound shown by the formula (II) is obtained after reaction solution is separated and purified. The synthesis method has the advantages of reasonable technology, low production cost, simple operation, high reaction yield, little catalyst amount, environment protection, and has a favorable popularization and application prospect; in addition, the catalyst can be recycled and reused.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of flavonoids. (2) Background technology [0002] Flavonoids belong to phenolic compounds, and there are at least 4,000 flavonoids with known chemical structures. Flavonoids have extensive and important biological activities and pharmacological effects, including: anti-oxidation, anti-inflammatory, anti-cancer, anti-mutagenic, anti-cardiovascular disease and other effects. Therefore, the synthesis of such compounds has important theoretical significance and application prospects, and has become an important research field of organic chemistry. [0003] One of the classic synthetic methods of flavonoids is to use o-hydroxyacetophenone and aryl formyl chloride (or aryl formic anhydride or aryl formic acid) to generate esters, then rearrange to generate β-propanedione intermediates, and finally Cyclization produces flavonoids. Wherein the cyclization reaction generally uses acid catalysts such as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
CPCY02P20/584
Inventor 吴华悦何飞苏为科陈久喜
Owner WENZHOU UNIVERSITY
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