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Method for preparing quinoline compounds under catalysis of zirconocene dichloride

A technology of zirconocene dichloride and catalytic preparation, applied in the direction of organic chemistry, etc., to achieve the effect of mild reaction conditions, simple operation and less dosage

Active Publication Date: 2019-08-23
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the shortcomings of the existing preparation methods of quinoline compounds, and provide a method for preparing quinoline compounds with simple operation, mild reaction conditions and high efficiency

Method used

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  • Method for preparing quinoline compounds under catalysis of zirconocene dichloride
  • Method for preparing quinoline compounds under catalysis of zirconocene dichloride
  • Method for preparing quinoline compounds under catalysis of zirconocene dichloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Preparation of 2,4-diphenylquinoline with the following structural formula

[0018]

[0019] Add 0.103g (0.5mmol) 1,4-diphenyl-3-butyne-2-one, 0.0073g (0.025mmol) zirconocene dichloride, 0.0082g (0.05mmol) L-phenylpropane to the reaction flask Amino acid, 64μL (0.6mmol) o-aminobenzenethiol, 1mL DMF, stirred and reacted at 30°C for 5 hours, then added 0.1518g (0.6mmol) iodine, continued to stir and reacted at 30°C for 2 hours, stopped the reaction, added Add 10 mL of saturated sodium thiosulfate aqueous solution, add 10 mL of ethyl acetate and extract 3 times, remove the ethyl acetate by rotary evaporation of the organic phase, and separate with a silica gel column (the eluent is petroleum ether and dichloromethane in a volume ratio of 2:1) Mixed liquor), obtains 2,4-diphenylquinoline, and its productive rate is 93%, and the spectral data of product is: 1 H NMR (400MHz, CDCl 3 )δ8.16(d, J=8.4Hz, 1H), 8.10(d, J=7.4Hz, 2H), 7.81(d, J=8.3Hz, 1H), 7.72(s, 1H), 7.63(t, ...

Embodiment 2

[0025] Preparation of 2-(4-chlorophenyl)-4-phenylquinoline with the following structural formula

[0026]

[0027] In this example, the 1,4-diphenyl-3-butane used in Example 1 was replaced with equimolar 1-(4-chlorophenyl)-4-phenyl-3-butyn-2-one Alkyn-2-ketone, other steps are identical with embodiment 1, obtain 2-(4-chlorophenyl)-4-phenylquinoline, and its productive rate is 84%, and the spectral data of product is: 1 H NMR (400MHz, CDCl 3 )δ8.12(d, J=8.4Hz, 1H), 8.05(d, J=8.4Hz, 2H), 7.80(d, J=8.3Hz, 1H), 7.68-7.60(m, 2H), 7.44( s,5H),7.38(d,J=8.2Hz,3H); 13 C NMR (101MHz, CDCl 3 )δ155.51, 149.41, 148.78, 138.27, 138.03, 135.58, 130.11, 129.70, 129.55, 129.01, 128.84, 128.65, 128.51, 126.55, 125.84, 125.69, 118.89.

Embodiment 3

[0029] Preparation of 2-(4-fluorophenyl)-4-phenylquinoline of the following structural formula

[0030]

[0031] In this example, the 1,4-diphenyl-3-butane used in Example 1 was replaced with equimolar 1-(4-fluorophenyl)-4-phenyl-3-butyn-2-one Alkyn-2-one, other steps are the same as in Example 1, obtain 2-(4-fluorophenyl)-4-phenylquinoline, its productive rate is 90%, and the spectral data of product is: 1 H NMR (400MHz, CDCl 3 )δ8.16-8.06 (m, 3H), 7.83-7.77 (m, 1H), 7.69-7.60 (m, 2H), 7.49-7.40 (m, 5H), 7.38 (ddd, J = 8.2, 6.8, 1.3 Hz,1H),7.11(t,J=8.7Hz,2H); 13 C NMR (101MHz, CDCl 3 )δ165.07,162.59,155.76,149.35,148.77,138.32,135.81,135.77,130.04,129.66,129.55,129.48,129.39,128.63,128.48,126.40,125.70,125.68,118.98,115.88,115.67.

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Abstract

The invention discloses a method for preparing quinoline compounds under catalysis of zirconocene dichloride. According to the method, 3-butyne-2-one compounds and an o-aminophenylmercaptan compound are taken as raw materials, zirconium dichloride is taken as a catalyst, L-phenylalanine, tyrosine and the like are taken as catalyst ligands, and N,N-dimethylformamide is used as a solvent, and elemental iodine, hydrogen peroxide, peroxy tert-butyl alcohol and the like are used as oxidizing agents, so that the quinoline compound can be prepared in a high-efficiency and high-yield manner. The catalyst used in the method is less in use amount, low in cost and stable in air, reaction conditions are mild, and operation is simple. After the reaction is finished, the product is extracted and washed,simple column chromatography separation is carried out, and then the quinoline compound can be obtained. The method provides a low-cost efficient way for preparation of the quinoline compound and hasa wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of synthesis of quinoline compounds, in particular to a method for efficiently preparing quinoline compounds by catalyzing the reaction of zirconocene 3-butyn-2-one compounds and o-aminobenzenethiol compounds with dichlorozirconocene . Background technique [0002] Quinolines are a class of alkaloids that exist widely, and are often used in medicine, pesticides, dyes, etc., and have attracted people's attention because of their extensive biological and pharmacological effects. The quinoline pharmacophore has important functions, and it has been reported to have a variety of pharmacological activities, such as: anti-cancer, anti-malarial, anti-tuberculosis, anti-bacterial, anti-inflammatory, antioxidant, anti-hypertensive, anti-AIDS, treatment of lupus erythematosus And neurodegenerative diseases, etc., it is of great significance in medicine and organic synthesis. [0003] At present, there are various met...

Claims

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Application Information

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IPC IPC(8): C07D215/06C07D215/12C07D215/18
CPCC07D215/06C07D215/12C07D215/18
Inventor 高子伟杨明明苏洁庄梦媛孙华明
Owner SHAANXI NORMAL UNIV
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