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Method for preparing flavonoid derivative containing pyrazole structural unit

A technology for structural units and flavonoids is applied in the field of preparation of flavonoid derivatives, and can solve the problems of harmful compound operation process, cumbersome, expensive reagents and the like

Inactive Publication Date: 2010-06-30
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods often require harsh reaction conditions, expensive reagents or compounds that are harmful to the environment, and the operation process is cumbersome, etc.

Method used

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  • Method for preparing flavonoid derivative containing pyrazole structural unit
  • Method for preparing flavonoid derivative containing pyrazole structural unit
  • Method for preparing flavonoid derivative containing pyrazole structural unit

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Experimental program
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Effect test

Embodiment 1

[0024] Embodiment 1: Preparation of flavonoid derivatives containing pyrazole structural unit

[0025] Product 2a: Put bis(trichloromethyl)carbonate (1.49g, 5mmol) into a dry 100mL three-neck flask equipped with mechanical stirring, drying tube, thermometer, etc., and cool to 0-5 At °C, a dichloromethane solution (4 mL) of N,N-dimethylformamide (1.31 g, 17.9 mmol) was added dropwise, the ice bath was removed after the drop, and the Vilsmeier reagent was prepared by allowing to rise to room temperature. Add the flavanone-4-hydrazone compound 1a (2.36g, 7.5mmol) represented by the prepared raw material formula (I), and heat the reaction mixture to 30-35°C for 4 hours. After the reaction, the reaction solution was added to ice water, stirred, and then saturated NaHCO 3 The pH of the solution was adjusted to neutral, and the layers were separated. The aqueous layer was extracted three times with dichloromethane (15ml×3). The dichloromethane layers were combined, washed with satur...

Embodiment 2

[0026] Embodiment 2: Preparation of flavonoid derivatives containing pyrazole structural unit

[0027] Product 2a: Put bis(trichloromethyl)carbonate (2.97g, 10mmol) into a 100mL three-necked flask equipped with mechanical stirring, drying tube, thermometer, etc., and cool to 0-5 At °C, a dichloromethane solution (8 mL) of N,N-dimethylformamide (2.63 g, 36 mmol) was added dropwise, the ice bath was removed after the drop, and the Vilsmeier reagent was prepared by allowing to rise to room temperature. Add the flavanone-4-hydrazone compound 1a (2.36g, 7.5mmol) represented by the prepared raw material formula (I), and heat the reaction mixture to 30-35°C for 4 hours. After the reaction, the reaction solution was added to ice water, stirred, and then saturated NaHCO 3The pH of the solution was adjusted to neutral, and the layers were separated. The aqueous layer was extracted three times with dichloromethane (15ml×3). The combined dichloromethane layers were washed with saturated ...

Embodiment 3

[0028] Embodiment 3: Preparation of flavonoid derivatives containing pyrazole structural unit

[0029] Product 2a: Put bis(trichloromethyl)carbonate (4.46g, 15mmol) into a dry 100mL three-neck flask equipped with mechanical stirring, drying tube, thermometer, etc., and cool to 0-5 At °C, a dichloromethane solution (12 mL) of N,N-dimethylformamide (3.94 g, 54.0 mmol) was added dropwise, the ice bath was removed after the drop, and the Vilsmeier reagent was prepared by allowing to rise to room temperature. Add the flavanone-4-hydrazone compound 1a (2.36g, 7.5mmol) represented by the prepared raw material formula (I), and heat the reaction mixture to 30-35°C for 4 hours. After the reaction, the reaction solution was added to ice water, stirred, and then saturated NaHCO 3 The pH of the solution was adjusted to neutral, and the layers were separated. The aqueous layer was extracted three times with dichloromethane (15ml×3). The combined dichloromethane layers were washed with satu...

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Abstract

The invention relates to a method for preparing flavonoid derivative containing a pyrazole structural unit, which includes the following steps that: bis(trichloromethyl) carbonate and N,N-dimethylformamide as materials are pre-reacted, so that Vilsmeier reagent is prepared, flavanone-4-hydrazone compound shown as the formula (I) is added in the Vilsmeier reagent under the temperature of 0 DEG C to 5 DEG C, reaction then takes place for 2 to 6 hours after the temperature is raised to 30 DEG C to 80 DEG C, and after the reaction is finished, reaction solution is separated and purified, so that the flavonoid derivative containing the pyrazole structural unit, shown as the formula (II), is obtained; the ratio between the flavanone-4-hydrazone compound, the bis(trichloromethyl) carbonate and the N,N-dimethylformamide is 1:0.6 to 2:2.4 to 7.2; in the formula (I) and the formula (II), R1 of ring A is H or CH3, ring B is unsubstituented, monosubstituented or multisubstituented, n is 1 or 2, and R2 is H, Cl and CH3O. The invention has the advantages of mild reaction conditions, easy operation, high reaction yield, little pollution, environment-friendliness and the like.

Description

(1) Technical field [0001] The invention relates to a preparation method of a flavonoid derivative containing a pyrazole structural unit. (2) Background technology [0002] Flavonoids are important compounds in organic chemistry, natural product chemistry and polymer chemistry. It has been reported in the literature that flavonoids have pharmacological activities such as anti-allergic, anti-cancer, cholesterol-lowering, anti-bacterial, and anti-rheumatic. Pyrazole ring compounds also have a wide range of biological activities, such as antibacterial, antitumor, anti-inflammatory, hypoglycemic, intestinal anthelmintic and anti-tuberculosis activities. It is also a very important structure in many compounds with pharmacological activity. In recent years, the research on the synthesis and biological activity of pyrazole compounds has been paid more and more attention by chemists. It is a work of practical significance to find a convenient synthesis method of flavonoid derivativ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052
Inventor 苏为科陈志卫施湘君杨艳艳
Owner ZHEJIANG UNIV OF TECH
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