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Application of biomass-supported copper-catalyzed three-component reaction in preparation of fluorine-containing medicine

A biomass and copper-catalyzed technology, applied in physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, organic chemistry, etc., can solve the problems of limited practicability due to reaction conditions, and achieve good yields, The effect of promoting industrialization and efficient recycling capabilities

Active Publication Date: 2021-09-28
ZHEJIANG SHUREN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the presence of noble metals and toxic transition metals, harsh reaction conditions, and high catalytic loading greatly limit the practicality of these methods

Method used

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  • Application of biomass-supported copper-catalyzed three-component reaction in preparation of fluorine-containing medicine
  • Application of biomass-supported copper-catalyzed three-component reaction in preparation of fluorine-containing medicine
  • Application of biomass-supported copper-catalyzed three-component reaction in preparation of fluorine-containing medicine

Examples

Experimental program
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Effect test

preparation example Construction

[0045] Preparation of Chitosan-supported Copper Catalyst

[0046] In a 100 mL round bottom flask, dissolve anhydrous copper acetate in H 2 O middle. Chitosan was then added to the solution to obtain a suspension which was stirred at 40 °C for 8 h. After the solution was cooled to room temperature, the H was slowly removed by suction filtration under reduced pressure. 2 O, the filter cake was washed three times with ethanol and water to give a light blue solid. The obtained light blue solid was dried under vacuum at 60 °C for 12 hours; different Cu(OAc) 2 Loaded chitosan-supported copper catalyst. The chitosan supported copper catalyst was named Cu(OAc) 2 @CS. Different Cu(OAc) 2Catalysts with loads were prepared according to the above method, and catalysts with loads of 10, 15, 20, and 30 mol% were prepared respectively, named as Cu(OAc) 2 @CS-10, Cu(OAc) 2 @CS-15, Cu(OAc) 2 @CS-20, Cu(OAc) 2 @CS-30.

Embodiment 1

[0048] The preparation of N-methylquinoxalinone (R in structural formula (II) 1 is methyl, R 2 for H)

[0049] In a 100mL round bottom flask, add 2-hydroxyquinoxalinone (12mmol, 1.75g), potassium hydroxide (42mmol, 2.36g), 15mL N,N-dimethylformamide (DMF), under ice bath After stirring, a DMF solution of iodomethane (14.4 mmol, 2 g) was added dropwise to the round bottom flask. After the dropwise addition, the reaction was continued at room temperature for 6 hours, and the reaction was detected by TLC. After the reaction was completed, the reaction solution was washed with saturated ammonium chloride solution, extracted with ethyl acetate, and the organic phase was washed with brine, the organic phase was separated, dried, spin-dried, and extracted with petroleum ether and ethyl acetate (10:1 ) ratio is that the eluent is purified through the column, and N-methylquinoxalinone is obtained after drying.

[0050] The preparation of N-methylindole (R in structural formula (III)...

Embodiment 2

[0057] Effect of Different Catalysts

[0058] Chitosan supported copper acetate Cu(OAc) 2 @CS-10, Cu(OAc) 2 @CS-20, Cu(OAc) 2 @CS-30 replaces Cu(OAc) 2 @CS-15, the yields of the prepared target products were 76%, 87%, and 81%, respectively.

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Abstract

The invention relates to an application of a biomass-supported copper-catalyzed three-component reaction in preparation of a fluorine-containing medicine, which comprises the following steps: catalyzing quinoxalinone and derivatives thereof, indole and derivatives thereof and sodium trifluoromethanesulfinate by using a copper catalyst taking chitosan as a carrier, so as to synthesize the 3-(2-(trifluoromethyl)-indol-3-yl) quinoxalin-2-one derivative from the three components by a one-pot method. The heterogeneous biomass copper-loaded catalyst is adopted to catalyze the reaction, and the problems that a traditional homogeneous catalyst cannot be recycled, and metal residues exist are solved; and the 3-(2-(trifluoromethyl)-indol-3-yl)quinoxalin-2-one compound with different substituent groups is expanded, the biomass supported copper catalyst can be cyclically catalyzed for multiple times, the target product keeps good yield, and it is indicated that the catalyst has efficient cycle capacity and can promote the possibility of industrialization of a reaction system.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to the application of a biomass-loaded copper-catalyzed three-component reaction in the preparation of fluorine-containing medicines. Background technique [0002] Trifluoromethyl-containing compounds are important components of natural products, functional materials and drugs, such as the antidepressant fluoxetine, AIDS-specific drug efavirenz, and pyrethroid insecticides, etc., and their structural formulas are as follows: [0003] [0004] They play an important role in biology and medicine, so it is necessary to continuously explore more efficient and concise trifluoromethylation methods. Typical methods for trifluoromethylation include transition metal-catalyzed trifluoromethylation of phenylboronic acids, halogenated hydrocarbons, carboxylic acids, anilines, and C–H compounds. However, the presence of noble metals and toxic transition metals, harsh r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04B01J31/06
CPCC07D403/04B01J31/06Y02P20/584
Inventor 沈超郑凯章乐天徐好孙娜波朱丹诚乔军
Owner ZHEJIANG SHUREN UNIV
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