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A method for one-step synthesis of flavonoids catalyzed by 1,3-dialkylimidazolium oxometalates

A technology for flavonoids and dialkylimidazoles, which is applied in the field of synthesizing flavonoids, can solve the problems of low yield of flavonoids, complicated operation and the like, and achieves the effects of improving synthesis efficiency, concise operation steps and high product yield

Active Publication Date: 2018-11-23
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it should be pointed out that the synthesis of flavonoids via the chalcone route still requires multiple independent synthesis steps such as condensation dehydration, intramolecular ring formation, and oxidative dehydrogenation, and the catalysts required for each step are different, and the operation is very complicated. cumbersome and consistently low yields of flavonoids

Method used

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  • A method for one-step synthesis of flavonoids catalyzed by 1,3-dialkylimidazolium oxometalates
  • A method for one-step synthesis of flavonoids catalyzed by 1,3-dialkylimidazolium oxometalates
  • A method for one-step synthesis of flavonoids catalyzed by 1,3-dialkylimidazolium oxometalates

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of flavonoids

[0026] Ionic liquid catalyst 1-butyl-3-methylimidazolium molybdate (abbreviated as [Bmim] 2 [MoO 4 ]), its structural formula is:

[0027]

[0028] In a 10mL reactor, add 0.2122g (2mmol) benzaldehyde, 0.2723g (2mmol) 2-hydroxyacetophenone, 0.8174g (8mmol) solvent n-hexanol and 0.2630g (0.6mmol) ionic liquid catalyst [Bmim] successively 2 [MoO 4 ], stir and mix evenly, heat up to the reaction temperature of 70°C, stir and react in an open environment for 3h, cool to room temperature after the reaction, add water for extraction, stand for phase separation, and remove the solvent n-hexanol from the upper phase by vacuum distillation , and then separated by column chromatography and recrystallization to obtain the target product flavone, the yield is 98%, and its structural formula is determined by proton nuclear magnetic resonance spectrum, carbon spectrum and high resolution mass spectrometry:

[0029]

[0030] The low...

Embodiment 2

[0031] Embodiment 2: the synthesis of 4'-methylflavone

[0032] Ionic liquid catalyst 1-ethyl-3-methylimidazolium vanadate (abbreviated as [Emim] 2 [VO 4 ]), its structural formula is:

[0033]

[0034] In a 10mL reactor, add 0.2403g (2mmol) 4-methylbenzaldehyde, 0.2723g (2mmol) 2-hydroxyacetophenone and 0.2024g (0.6mmol) ionic liquid catalyst [Emim] 2 [VO 4 ], and 0.4085g (4mmol) tetrahydrofurfuryl alcohol solvent, after stirring and mixing uniformly, heat up to the reaction temperature of 50°C, stir and react for 3h under an oxygen atmosphere of 0.1MPa, cool to room temperature after the reaction, and remove the solvent by distillation under reduced pressure After tetrahydrofurfuryl alcohol, add ethyl acetate and water to extract, let stand to separate the phases, and then separate the upper phase through column chromatography and recrystallization to obtain the target product 4'-methylflavone with a yield of 95%. , carbon spectrum and high-resolution mass spectrometry ...

Embodiment 3

[0036] Embodiment 3: the synthesis of 2'-chloroflavone

[0037] Ionic liquid catalyst 1-propyl-3-methylimidazolium vanadate (abbreviated as [Pmim] 2 [VO 4 ]), its structural formula is:

[0038]

[0039] In a 10mL reactor, add 0.2811g (2mmol) 2-chlorobenzaldehyde, 0.2723g (2mmol) 2-hydroxyacetophenone and 0.1461g (0.4mmol) ionic liquid catalyst [Pmim] 2 [VO 4 ], and 0.3724g (6mmol) ethylene glycol solvent, after stirring and mixing evenly, heat up to the reaction temperature of 60°C, stir and react for 3h under an oxygen atmosphere of 0.1MPa, cool to room temperature after the reaction, and remove the solvent by distillation under reduced pressure After ethylene glycol, add ethyl acetate and water for extraction, let stand to separate the phases, and then separate the upper phase through column chromatography and recrystallization to obtain the target product 2'-chloroflavone with a yield of 94%. Carbon spectrum and high-resolution mass spectrometry determine that its s...

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Abstract

The invention discloses a method for catalyzing one-step synthesis of flavonoids by using 1,3-dialkylimidazole oxometalate. ‑Hydroxyacetophenone or 2‑hydroxyacetophenone derivatives, ionic liquid catalyst, and organic solvent, stirred and heated to 50-90°C, then using oxygen or air as oxidant, reacting at constant temperature for 2-7 hours, cooling, and depressurizing After separation by distillation, column chromatography and recrystallization, the target flavonoids are obtained. The biggest feature of the present invention is that ionic liquid is used as a catalyst, and the yield of one-step synthesis of flavonoids is as high as 85%. Therefore, compared with the existing synthesis method, the present invention shortens the reaction steps and significantly improves the synthesis of flavonoids Efficiency, with the advantages of high product yield, low production cost, simple operation steps, mild reaction conditions, etc., so it is considered to be a new method for efficiently synthesizing flavonoids.

Description

technical field [0001] The invention relates to a method for synthesizing flavonoids, in particular to a method for synthesizing flavonoids in one step by catalyzing 1,3-dialkylimidazolium oxymetalate. Background technique [0002] Flavones, flavanones, isoflavones, flavonols and other flavonoids are an important class of natural products, because they have anti-tumor, anti-bacterial, anti-viral, anti-aging, liver protection, cardiovascular system protection, blood pressure, and blood lipids , analgesic and many other physiological activities, there is a huge demand in many fields such as health food, medicine and cosmetics. However, at present, flavonoids are mainly extracted and separated from natural plants by water extraction or organic solvent extraction. The shortcomings of this traditional method are very obvious, not only the extraction efficiency is extremely low (only 3%-5%), and The components of the extracted product are complex, and the flavonoids of a single c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/30B01J31/02
CPCB01J31/0284B01J2231/766C07D311/30
Inventor 陶端健黄伟宋智彬陈凤凤周言
Owner JIANGXI NORMAL UNIV
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