Method for preparing quinazolone and derivatives thereof by using chitosan-loaded copper catalyst

A technology of copper catalyst and chitosan, which is applied in the field of compound synthesis, can solve problems such as long reaction time, large environmental pollution, and residues

Pending Publication Date: 2021-05-11
HUBEI ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above method solves the problems existing in the traditional preparation process, but there are also deficiencies, for example, the reaction time is longer, and the low-priced copper generated by reduction will remain in the solvent, which will cause great environmental pollution.

Method used

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  • Method for preparing quinazolone and derivatives thereof by using chitosan-loaded copper catalyst
  • Method for preparing quinazolone and derivatives thereof by using chitosan-loaded copper catalyst
  • Method for preparing quinazolone and derivatives thereof by using chitosan-loaded copper catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation method of compound III-1, its steps are:

[0033]

[0034] A. Add a magnetic stirrer in the reaction tube, seal it and connect it to a vacuum device; evacuate for 5 minutes and then continue to feed argon for 1 min. Repeat the above operation 3 times to completely remove the oxygen in the reaction tube; after continuously feeding argon Add 5 mg of chitosan-supported cuprous iodide (CS@CuI) (0.00001mol) and starting material I-1 to the reaction tube in sequence: (124.0mg, 0.5mmol), II-1: (79.1mg, 0.75mmol) and sodium carbonate (132.5mg, 1.25mmol), dissolved in 3mL mixed solvent (isopropanol: water = 9:1), stirred at 90°C for 12h;

[0035] B. After the reaction is finished, filter the entire reaction system and wash with 20 mL of ethyl acetate. Chitosan-supported cuprous iodide (CS@CuI) was recovered by filtration, and the filtrate was evaporated and concentrated, and the residue was separated and purified by column chromatography with different pro...

Embodiment 2

[0040] The preparation method of compound III-2, its steps are:

[0041]

[0042] A. Add a magnetic stirrer in the reaction tube, seal it and connect it to a vacuum device; evacuate for 5 minutes and then continue to feed argon for 1 min, repeat the above operation 3 times and completely remove the oxygen in the reaction tube; after continuously feeding argon Add 5 mg of chitosan-supported cuprous iodide (CS@CuI) (0.00001mol) and starting material I-1 to the reaction tube in sequence: (124.0mg, 0.5mmol), II-2: (89.7mg, 0.75mmol) and sodium carbonate (132.5mg, 1.25mmol), dissolved in 3mL mixed solvent (isopropanol:water=9:1)), stirred at 90°C for 12h;

[0043] B. After the reaction is finished, filter the entire reaction system and wash with 20 mL of ethyl acetate. Chitosan-supported cuprous iodide (CS@CuI) was recovered by filtration, and the filtrate was evaporated and concentrated. The residue was separated and purified by column chromatography with different proporti...

Embodiment 3

[0047] The preparation method of compound III-3, its steps are:

[0048]

[0049] A. Add a magnetic stirrer in the reaction tube, seal it and connect it to a vacuum device; evacuate for 5 minutes and then continue to feed argon for 1 min, repeat the above operation 3 times and completely remove the oxygen in the reaction tube; after continuously feeding argon Add 5 mg of chitosan-supported cuprous iodide (CS@CuI) (0.00001mol) and starting material I-1 to the reaction tube in sequence: (124.0mg, 0.5mmol), II-3: (101.3mg, 0.75mmol) and sodium carbonate (132.5mg, 1.25mmol), dissolved in 3mL mixed solvent (isopropanol: water = 9:1), stirred at 90°C for 12h;

[0050] B. After the reaction is finished, filter the entire reaction system and wash with 20 mL of ethyl acetate. Chitosan-immobilized cuprous iodide (CS@CuI) was recovered by filtration, and the filtrate was evaporated and concentrated. The residue was separated and purified by column chromatography with different pro...

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PUM

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Abstract

The invention discloses a method for preparing quinazolone and derivatives thereof by using a chitosan-loaded copper catalyst, which comprises the following steps of replacing residual gas in a reaction container with inert gas, adding a catalytic amount of copper ion-loaded chitosan catalyst, substituted 2-halogenated benzoic acid, substituted amidine hydrochloride, inorganic alkali and a mixed solvent into the reaction container, and heating for reaction, after the reaction time is 2-18 hours, extracting the product by using ethyl acetate, filtering and recovering the copper ion-loaded chitosan catalyst, concentrating the filtrate under reduced pressure, and purifying the product by column chromatography. The method has the advantages of low catalyst dosage, recoverability, easy separation after reaction, no metal residue, simple post-treatment, and suitableness for large-scale production.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a method for preparing quinazolones and derivatives thereof with a chitosan-loaded copper catalyst. Background technique [0002] Quinazolones and their derivatives are a large class of alkaloids, which widely exist in nature and have excellent biological and pharmaceutical activities. They are often used in medical treatment for hypnosis, sedation, analgesia, antispasmodics, antitussive, and antibacterial , anti-diabetic, anti-inflammatory and anti-tumor agents. Therefore, the development of a practical and effective method to construct the quinazolone skeleton structure has received widespread attention. The traditional synthesis methods of quinazolones derivatives mostly use o-amino or o-nitrobenzoic acid derivatives which are difficult to prepare as raw materials, and they need to be prepared in toxic organic solvents, and at the same time, specific ligands need to be used ...

Claims

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Application Information

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IPC IPC(8): C07D239/90C07D239/88C07D239/91B01J31/22
CPCC07D239/90C07D239/88C07D239/91B01J31/2217B01J2531/16B01J2531/0213B01J2231/4277Y02P20/584
Inventor 朱磊韩彪文蔚张瑶瑶李博解夏彩芬颜永斌李伟汪连生
Owner HUBEI ENG UNIV
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