Method for synthesizing quinoline by aromatic amine and diketone

A technology of aromatic amines and derivatives, which is applied in the field of synthesis of quinoline derivatives, can solve the problems of complex reaction steps, poor reaction effect, strong substrate restriction, etc., and achieves easy separation and purification, simple operation steps and low cost Effect

Inactive Publication Date: 2015-12-30
NANYANG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But these methods also have many disadvantages: harsh reaction conditions, high reaction temperature, some require high temperature and high pressure, difficult separation, strong substrate restriction of the reaction
However, there are still some shortcomings in this patent: for example, the reaction substrate enone or enaldehyde needs to be synthesized and purified, the reaction steps are relatively complicated, and the steric effect of the reaction substrate amine is relatively obvious. , the response is not good

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  • Method for synthesizing quinoline by aromatic amine and diketone

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Experimental program
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Effect test

Embodiment 1

[0028] The synthetic method of 2-methyl-4-phenylquinoline is as follows: in reaction vessel, add aniline 0.5mmol (46.5mg), 1-phenyl-1,3-butanedione 0.5mmol (81mg), catalyst AgOTf0. 005mmol (1.29mg) and HOTf0.01mmol (1.5mg), toluene 2mL. React in an oil bath at 120°C for 24 hours, cool to room temperature, add water to quench the reaction, wash three times with ethyl acetate, separate the layers, combine the organic layers, decolorize with activated carbon, filter, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and the product passes through Purified by column chromatography, the eluent was petroleum ether:ethyl acetate=10:1 (v / v), and a white solid product was obtained with a yield of 82% and a purity of 99.8%. 1 HNMR (400MHz, CDCl 3 ) δ ppm: 8.75 (d, J =7.6Hz, 1H), 7.88-8.23(m, 6H), 7.61(m, 3H), 3.04(s, 3H); 13 CNMR (400MHz, CDCl 3 ) δ ppm: 157.9, 154.2, 135.1, 133.5, 130.1, 130.0, 129.9, 129.8, 129.1, 127.1, 124.7, 122.3, 121.6, 20.4; HRMS (EI) ...

Embodiment 2

[0030] 2, the synthetic method of 8-dimethyl-4-phenylquinoline is as follows: in reaction vessel, add o-methylaniline 0.5mmol (53.5mg), 1-phenyl-1, 3-butanedione 0.5mmol ( 81mg), catalyst AgOTf0.005mmol (1.29mg) and HOTf0.01mmol (1.5mg), toluene 2mL. React in an oil bath at 120°C for 24 hours, cool to room temperature, add water to quench the reaction, wash three times with ethyl acetate, separate the layers, combine the organic layers, decolorize with activated carbon, filter, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and the product passes through Purified by column chromatography, the eluent was petroleum ether:ethyl acetate=10:1 (v / v), and a white solid product was obtained with a yield of 78% and a purity of 99.7%. 1 HNMR (400MHz, CDCl 3 ) δ ppm: 8.23 ​​(d, J =8.0Hz, 2H), 7.79(d, J =8.4Hz, 1H), 7.69(s, 1H), 7.36-7.54(m, 5H), 2.89(s, 3H), 2.69(s, 3H); 13 CNMR (400MHz, CDCl 3 ) δ ppm: 155.1, 147.1, 144.8, 140.0, 138.2, 129.5, 129.2, 128.8...

Embodiment 3

[0032] 2, the synthetic method of 7-dimethyl-4-phenylquinoline is as follows: in reaction vessel, add m-methylaniline 0.5mmol (53.5mg), 1-phenyl-1, 3-butanedione 0.5mmol ( 81mg), catalyst AgOTf0.005mmol (1.29mg) and HOTf0.01mmol (1.5mg), toluene 2mL. React in an oil bath at 120°C for 24 hours, cool to room temperature, add water to quench the reaction, wash three times with ethyl acetate, separate the layers, combine the organic layers, decolorize with activated carbon, filter, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and the product passes through Purified by column chromatography, the eluent was petroleum ether: ethyl acetate = 10:1 (v / v), to obtain a white solid product with a yield of 84% and a purity of 99.9%. 1 HNMR (400MHz, CDCl 3 ) δ ppm: 8.53 (d, J =7.6Hz, 1H), 8.06(m, 3H), 7.69(s, 1H), 7.59-7.68(m, 4H), 2.99(s, 3H), 2.65(s, 3H); 3 CNMR (400MHz, CDCl 3 ) δ ppm: 157.5, 153.5, 147.3, 138.4, 133.3, 132.0, 130.03, 129.96, 128.9, 125.3, ...

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Abstract

The invention provides a method for synthesizing quinoline by aromatic amine and diketone and belongs to the technical field of synthesis of the quinoline. According to the method for synthesizing the quinoline by the aromatic amine and the diketone, under the existence of silver trifluoromethanesulfonate and trifluoromethanesulfonic acid, the quinoline is synthesized by reaction between the aromatic amine compound and the diketone compound; the reaction general formula is shown in the specification. Compared with the prior art, the method not only is suitable for a large number of functional groups but also is simple in operation, high in yield, single in product structure, convenient for separation and purification, safe, low in cost and low in pollution.

Description

technical field [0001] The invention belongs to the technical field of synthesis of quinoline derivatives, in particular to a method for synthesizing quinoline derivatives by using aromatic amines and diketones. Background technique [0002] With the progress of human society and the rapid development of science and technology, people's expectations for life and quality of life are getting higher and higher, and people's awareness of health care is getting stronger and stronger, which also promotes the rapid development of the pharmaceutical industry, thus developing more and more Effective new drugs, wherein the synthesis of new drugs by chemical methods is an important way to research and develop new drugs. [0003] Quinoline derivatives are a very important class of nitrogen-heterocyclic compounds. This type of compound has good biological activities such as antibacterial, antitumor and antituberculosis, and is one of the hotspots in the development and research of new d...

Claims

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Application Information

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IPC IPC(8): C07D215/06C07D215/20C07D215/18C07D215/12C07D221/10
CPCC07D215/06C07D215/12C07D215/18C07D215/20C07D221/10
Inventor 徐学锋张旭柳文敏孙如中闫彦磊
Owner NANYANG NORMAL UNIV
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