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Method for preparing 3-aryl-subsituted quinoline by 3-oxo-2,3-diarylpropionaldehyde

A technology of diarylpropanal and aryl, which is applied in the field of organic compound preparation, can solve the problems of toxicity and difficult synthesis of precursor aryl acetaldehyde, and achieve the effects of simple process, easy-to-obtain raw materials and high yield

Inactive Publication Date: 2011-05-25
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, using When preparing 3-aryl substituted quinolines, there is a shortcoming that the precursor aryl acetaldehyde is difficult to synthesize
People such as Lin reported the method for the synthesis of 3-phenyl substituted quinolines by the Vilsmeier-Haack reaction, but used the phosphorus tribromide reagent that is poisonous and easily releases corrosive gas in the reaction, and the yield is only 64% (Y. Wang, Eur. J. Org. Chem. 2009, 4165)

Method used

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  • Method for preparing 3-aryl-subsituted quinoline by 3-oxo-2,3-diarylpropionaldehyde
  • Method for preparing 3-aryl-subsituted quinoline by 3-oxo-2,3-diarylpropionaldehyde
  • Method for preparing 3-aryl-subsituted quinoline by 3-oxo-2,3-diarylpropionaldehyde

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Effect test

Embodiment 1

[0014] Embodiment 1: Preparation of one of 3-phenylquinolines of 3-aryl substituted quinolines

[0015] The raw material is 3-oxo-2,3-diphenylpropanal, one of the 3-oxo-2,3-diaryl propanals.

[0016] In the first step, dissolve 11.2g of 3-oxo-2,3-diphenylpropanal and 9.1g of anthranilaldehyde in 330g of chlorobenzene, add 0.4g of trifluoromethanesulfonic acid, and stir at 90°C Down, condensation reaction 1.5 hours, obtained solution;

[0017] In the second step, 11 g of potassium tert-butoxide was added to the solution prepared in the first step, stirred at 80° C., rearranged for 10 minutes, cooled, added 330 g of water, extracted with ethyl acetate, dried and purified by column chromatography, 8.2 g of 3-phenylquinoline was obtained, with a yield of 82%.

Embodiment 2

[0018] Embodiment 2: Preparation of one of 3-(4-methoxyphenyl) quinolines of 3-aryl substituted quinolines

[0019] The raw material is 3-oxo-2-(4-methoxyphenyl)-3-phenylpropanal, one of 3-oxo-2,3-diarylpropanals.

[0020] In the first step, 12.7g of 3-oxo-2-(4-methoxyphenyl)-3-phenylpropanal and 9.1g of anthranilaldehyde were dissolved in 330g of chlorobenzene, and 0.4g of tris Fluoromethanesulfonic acid, under stirring at 100°C, condensation reaction for 2 hours to obtain a solution;

[0021] In the second step, add 11 g of potassium tert-butoxide to the solution prepared in the first step, rearrange and react for 20 minutes at 100° C. under stirring, cool, add 330 g of water, extract with ethyl acetate, and purify by column chromatography after drying , to obtain 9.4 g of 3-(4-methoxyphenyl) quinoline, with a yield of 80%.

Embodiment 3

[0022] Embodiment 3: Preparation of one of 3-(3-methoxyphenyl) quinolines of 3-aryl substituted quinolines

[0023] The raw material is 3-oxo-2-(3-methoxyphenyl)-3-phenylpropanal, one of 3-oxo-2,3-diarylpropanals.

[0024] In the first step, 12.7g of 3-oxo-2-(3-methoxyphenyl)-3-phenylpropanal and 9.1g of anthranilaldehyde were dissolved in 330g of chlorobenzene, and 0.4g of Trifluoromethanesulfonic acid, 110 ℃ and under stirring, condensation reaction for 3 hours, obtained solution;

[0025] In the second step, add 11 g of potassium tert-butoxide to the solution prepared in the first step, rearrange and react for 10 minutes at 100° C. under stirring, cool, add 330 g of water, extract with ethyl acetate, and purify by column chromatography after drying , to obtain 8.8 g of 3-(3-methoxyphenyl) quinoline, yield 75%.

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Abstract

The invention discloses a method for preparing 3-aryl-subsituted quinoline by 3-oxo-2,3-diarylpropionaldehyde, and belongs to the technical field of organic compound preparation. The 3-aryl-subsituted quinoline is an intermediate of medicines and functional materials. 3-aryl quinoline with a yield of 75 to 82 percent is prepared by performing condensation and rearrangement reactions on 3-oxo-2,3-diarylpropionaldehyde serving as a raw material and o-amino benzaldehyde. The method has the advantages of readily available raw materials, simple process and high yield and is suitable for preparing the 3-aryl-subsituted quinoline.

Description

technical field [0001] 3-Aryl-substituted quinolines are intermediates in medicine and functional materials. The invention relates to a method for preparing 3-aryl substituted quinoline by using 3-oxo-2,3-diarylpropanal, which belongs to the technical field of organic compound preparation. Background technique [0002] Quinoline and its derivatives have a wide range of biological activities, such as anti-asthma, anti-inflammatory, anti-HIV-1, and inhibition of tyrosine kinase. Based on its importance in medicine and as a structural unit in drug synthesis, chemists have conducted in-depth research on the synthesis methods of different substituted quinolines. For example, acid (base) catalyzed condensation of o-aminobenzaldehyde (or o-aminophenyl ketone) with an aldehyde or ketone containing at least one methylene in the α-position of the carbonyl The reaction is one of the methods for efficient framework substitution of quinolines. In recent years, the group of Vander M.H...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/04C07D215/14C07D215/12
Inventor 汤杰杨帆于志超罗万荣仇文卫
Owner EAST CHINA NORMAL UNIV