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A kind of method utilizing aromatic amine, aromatic aldehyde, ketone to synthesize quinoline derivative

A technology of aromatic amines and aromatic aldehydes, applied in the field of synthesis of quinoline derivatives, can solve problems such as limited quinoline derivatives, complex reaction steps, and poor reaction effects, and achieve easy separation and purification, efficient preparation, and simple operation steps Effect

Inactive Publication Date: 2017-12-19
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But these methods also have many disadvantages: the reaction conditions are harsh, the reaction temperature is high, some require high temperature and high pressure, separation is difficult, and the substrate restriction of the reaction is strong. Therefore, the quinoline derivatives of the synthetic substituent are very limited
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

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 2, the synthetic method of 4-diphenylquinoline is as follows: in reaction vessel, add aniline 0.5mmol (46.5mg), benzaldehyde 0.5mmol (53mg), acetophenone 0.75mmol (90.1mg), catalyst AgOTf 0.005 mmol ( 1.29 mg), HOTf 0.01 mmol (1.5 mg), 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 94% and a purity of 99.9%. 1 HNMR (500MHz, CDCl 3 ) ppm: 8.43 (d, J =8.0Hz, 1H), 8.34 (d, J =8.0Hz, 2H), 8.00 (d, J =8.5Hz, 1H), 7.92 (s, 1H), 7.80 (t, 1H), 7.51-7.64 (m, 9H); 13 CNMR (500MHz, CDCl 3 ): 156.90, 149.23, 149.05, 139.77, 138.56, 130.3...

Embodiment 2

[0031] 6-trifluoromethyl-2, the synthetic method of 4-diphenylquinoline is as follows: in reaction vessel, add p-trifluoromethylaniline 0.5mmol (80.6mg), benzaldehyde 0.5mmol (53mg), acetophenone 0.75 mmol (90.1 mg), catalyst AgOTf 0.005 mmol (1.29 mg), HOTf 0.01 mmol (1.5 mg), toluene 2 mL. 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=5:1 (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: 8.32 (d, J=8.8Hz, 1H), 8.20 (t, 3H), 7.87 (d, J =8.0Hz, 2H), 7.44-7.55 (m, 8H); 13 CNMR (100MHz, CDCl 3 ) δ ppm: 158.9, 150.2, 150.0, 139.0, 137.5, 131....

Embodiment 3

[0033] 6-methyl-2, the synthetic method of 4-diphenylquinoline is as follows: in reaction vessel, add p-methylaniline 0.5mmol (53.5mg), benzaldehyde 0.5mmol (53mg), acetophenone 0.75mmol (90.1 mg), catalyst AgOTf 0.005 mmol (1.29 mg), HOTf 0.01 mmol (1.5 mg), 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 96% and a purity of 99.9%. 1 HNMR (500MHz, CDCl 3 ) ppm: 8.85 (d, J =9.0Hz, 1H), 8.15(t, 2H), 7.97(d, J =3.5Hz, 2H), 7.88 (s, 1H), 7.62-7.73 (m, 8H), 2.61 (s, 3H); 13 CNMR (500MHz, DMSO- d 6 ): 155.7, 153.4, 140.0, 139.4, 136.2, 13...

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Abstract

The invention provides a method for synthesizing a quinoline derivative by utilizing arylamine, aromatic aldehyde and ketone, and belongs to the technical field of the synthesis of the quinoline derivative. According to the method for synthesizing a quinoline derivative by utilizing arylamine, aromatic aldehyde and ketone, in the existence of silver trifluoromethanesulfonate and trifluoromethanesulfonic acid, the quinoline derivative is synthesized by virtue of the reaction of an arylamine compound, an aromatic aldehyde compound and ketone compound. A reaction general formula is as shown in the specification. Compared with the prior art, the method is not only applicable to a great amount of functional groups, but also is simple in operation, high in yield, single in product structure, convenient to separate and purify, safe, low in price and small 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, aromatic aldehydes and ketones. 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/06C07D215/14C07D409/04C07D221/16C07D215/18
CPCC07D215/06C07D215/14C07D215/18C07D221/16C07D409/04
Inventor 张旭徐学锋王志强徐坤于林涛赵强毛武涛闫彦磊
Owner NANYANG NORMAL UNIV
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