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Application of three-component reaction catalyzed by biomass-supported copper in the preparation of fluorine-containing drugs

A biomass, copper catalysis technology, applied in physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, organic chemistry, etc. Efficient recycling ability, the effect of promoting industrialization

Active Publication Date: 2022-05-13
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 three-component reaction catalyzed by biomass-supported copper in the preparation of fluorine-containing drugs
  • Application of three-component reaction catalyzed by biomass-supported copper in the preparation of fluorine-containing drugs
  • Application of three-component reaction catalyzed by biomass-supported copper in the preparation of fluorine-containing drugs

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 the application of a biomass-supported copper-catalyzed three-component reaction in the preparation of fluorine-containing medicines. The copper catalyst using chitosan as a carrier catalyzes quinoxalinone and its derivatives, indole and its derivatives and three Sodium fluoromethyl sulfinate, three-component one-pot synthesis of 3-(2-(trifluoromethyl)-indol-3-yl)quinoxaline-2-one derivatives. The invention adopts heterogeneous biomass-supported copper catalyst to catalyze the reaction, which solves the problems of non-recyclable and metal residue of traditional homogeneous catalysts; expands 3-(2-(trifluoromethyl)-indole-3 with different substituents ‑base) quinoxaline‑2‑ketone compounds, biomass-supported copper catalysts can catalyze the reaction for multiple cycles, and the target product maintains a good yield, indicating that the catalyst has an efficient cycle ability and promotes the possibility of industrialization of the 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 Patents(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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