A kind of preparation method of quinoline derivative

A technology of derivatives and quinoline, applied in the field of quinoline derivatives, can solve the problems of difficult by-products, high reaction temperature, harsh reaction conditions, etc., and achieve the effect of easy separation and purification, simple operation and single product

Inactive Publication Date: 2016-01-20
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There are many disadvantages in the current synthetic method: the main reason is that 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 , so a method for the synthesis of quinoline derivatives with substituents is limited
In addition, in the process of using metal catalysis, the activity of the catalyst is limited. These shortcomings make the operation of the preparation process more difficult, endanger the health of operators, and cause serious environmental pollution.
Yet the method for existing synthetic quinoline derivatives is ubiquitous: need active reaction substrate, reaction rate is low, reaction time is longer, by-product is much difficult to handle and the form of reaction is too single (resulting in the product that is synthesized has very little large limitations) and other disadvantages

Method used

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  • A kind of preparation method of quinoline derivative
  • A kind of preparation method of quinoline derivative
  • A kind of preparation method of quinoline derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation of 2,4-diphenylquinoline: Add 0.5mmol (46.5mg) of aniline, 0.005mmol (1.29mg) of catalyst AgOTf, 0.5mmol (103mg) of 1,3-diphenylpropynone into the reaction vessel, Toluene 2mL. at 60 o React in a C oil bath for 10 hours, cool to room temperature, extract the product with ethyl acetate, concentrate under reduced pressure, and purify the product by column chromatography to obtain a white solid product with a yield of 98%. 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 ):156.90,149.23,149.05,139.77,138.56,130.35,129.70,129.60,129.50,128.96,128.72,128.52,127.75,126.47,125.92,125.75,119.39); 21 h 15 N:[M + ], 281.1207; Found: 281.1204.

Embodiment 2

[0027] Preparation of 4-phenylquinoline: Add 0.5mmol (46.5mg) of aniline, 0.005mmol (1.29mg) of catalyst AgOTf, 0.5mmol (65mg) of 3-phenylpropynaldehyde, and 2mL of toluene into a reaction vessel. at 60 o React in a C oil bath for 10 hours, cool to room temperature, extract the product with ethyl acetate, concentrate under reduced pressure, and purify the product by column chromatography to obtain a white solid product with a yield of 94%.

Embodiment 3

[0029] Preparation of 4-phenyl-2-p-tolylquinoline: Add 0.5mmol (46.5mg) of aniline, 0.005mmol (1.29mg) of catalyst AgOTf, 3-phenyl-1-p-tolyl-?? Propyrone 0.5mmol (11.0mg), toluene 2mL. at 60 o React in a C oil bath for 8 hours, cool to room temperature, extract the product with ethyl acetate, concentrate under reduced pressure, and purify the product by column chromatography to obtain a white solid product with a yield of 92%. 1 HNMR (500MHz, CDCl 3 ) ppm: 8.36 (d, J =8.0Hz,1H),8.25(d, J =8.0Hz,2H),7.95-7.93(d, J =8.0Hz,1H),7.85(s,1H),7.81-7.74(m,1H),7.61-7.52(m,6H),7.38-7.36(d, J =8.0Hz,2H),2.46(s,3H); 13 CNMR (500MHz, CDCl 3 ):156.9,149.2,148.6,139.4,138.4,136.7,120.2,129.6,129.5,128.5,128.2,127.4,126.1,125.6,125.5,119.1,21.5;HRMS(EI)Calcd.forC 22 h 17 N:[M + ], 295.1369; Found: 295.1365.

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Abstract

The invention proposes a method for preparing quinoline derivatives, which uses silver trifluoromethanesulfonate to catalyze substituent aniline, enone and enal derivatives to synthesize quinoline derivatives. The invention is simple in operation, not only applicable to a large number of functional groups, but also high in yield, single product, convenient for separation and purification, safe and cheap, and less polluted.

Description

technical field [0001] The invention relates to quinoline derivatives, in particular to a method for preparing quinoline derivatives, which is a method for synthesizing quinoline derivatives by using silver trifluoromethanesulfonate to catalyze substituted aniline and acetylene ketone or alkyne aldehyde derivatives. Background technique [0002] Quinoline compounds are a very important class of compounds, which are widely distributed in nature and are important intermediates necessary for a variety of fine chemicals, and are effectively used in some functional materials, such as dyes, pigments, luminescent materials, etc. wait. The quinoline compounds that have been discovered also have a variety of pharmaceutical activities, such as treating malaria, anti-inflammatory and bactericidal, and killing cancer cells. Because quinolines have a wide range of uses, a variety of synthetic methods have been developed in recent years, mainly including Doebner-vonMiller, Combes, Conrad...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/06C07D215/14C07D215/20C07D215/18C07D215/12
CPCC07D215/06C07D215/12C07D215/14C07D215/18C07D215/20
Inventor 张旭徐学锋于林涛赵强王志强毛武涛
Owner NANYANG NORMAL UNIV
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