Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of synthetic method of 2,4-diaryl quinoline compound

A technology of diarylquinoline and synthetic method, which is applied in the direction of organic chemistry, and can solve the problems of long reaction time and easy self-condensation of raw materials

Active Publication Date: 2021-07-27
ZHEJIANG UNIV OF TECH
View PDF9 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods often have the disadvantages of long reaction time and self-condensation of raw materials.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthetic method of 2,4-diaryl quinoline compound
  • A kind of synthetic method of 2,4-diaryl quinoline compound
  • A kind of synthetic method of 2,4-diaryl quinoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The reaction formula is as follows:

[0058]

[0059] Dissolve 0.0599g 1a (0.2mmol) and 0.1082g tetrachloro-p-benzoquinone (0.44mmol) in 3mL of acetonitrile, and stir the reaction system magnetically at 80°C for 2h. After the reaction, concentrate under reduced pressure and separate through a silica gel column. Petroleum ether and ethyl acetate at a ratio of 20:1 were used as eluents, and the eluent containing the target product was collected and combined to evaporate the solvent to obtain 2a (0.0390 g) as a yellow solid with a yield of 66%. 1 H NMR (500MHz, CDCl 3 ):δ8.21-8.17(m,3H),7.80(s,1H),7.68(s,1H),7.61-7.53(m,8H),7.48(t,J=7.3Hz,1H),2.50( s,3H). 13 C NMR (126MHz, CDCl 3 ):δ156.0,148.5,147.4,139.8,138.7,136.2,131.7, 129.9,129.5,129.1,128.8,128.6,128.3,127.5,125.7,124.4,119.4,21.8.ESI m / z[M+H] + 296.1; HRMS(ESI):calcd.forC 22 h 17 N[M+H] + 296.1434; found 296.1435.

Embodiment 2

[0060] Example 2: 0.0599g 1a (0.2mmol) and 0.1000g DDQ (0.44mmol) were dissolved in 3mL of acetonitrile, and the reaction system was magnetically stirred at 80°C for 2h. After the reaction was completed, it was concentrated under reduced pressure and separated by a silica gel column. Petroleum ether and ethyl acetate at a ratio of 20:1 were used as eluents, and the eluents containing the target product were collected and combined to evaporate the solvent to obtain 2a (0.0284 g) as a yellow solid with a yield of 48%. 1 H NMR (500MHz, CDCl 3 ):δ8.21-8.17(m,3H),7.80(s,1H),7.68(s,1H),7.61-7.53(m,8H),7.48(t,J=7.3Hz,1H),2.50( s,3H). 13 C NMR (126MHz, CDCl 3 ):δ156.0,148.5,147.4,139.8,138.7,136.2,131.7, 129.9,129.5,129.1,128.8,128.6,128.3,127.5,125.7,124.4,119.4,21.8.ESI m / z[M+H] + 296.1; HRMS(ESI):calcd.forC 22 h 17 N[M+H] + 296.1434; found 296.1435.

Embodiment 3

[0061] Example 3: 0.0599g 1a (0.2mmol) and 0.1082g tetrachloro-p-benzoquinone (0.44mmol) were dissolved in 3mL of 1,4-dioxane, and the reaction system was magnetically stirred at 80°C for 2h. After the reaction, the Concentrated under reduced pressure, separated by silica gel column, using petroleum ether and ethyl acetate at a volume ratio of 20:1 as the eluent, collecting and combining the eluent containing the target product and evaporating the solvent to obtain 2a (0.0431g) as a yellow solid, The yield was 73%. 1 H NMR (500MHz, CDCl 3 ):δ8.21-8.17(m,3H),7.80(s,1H),7.68(s,1H), 7.61-7.53(m,8H),7.48(t,J=7.3Hz,1H),2.50( s,3H). 13 C NMR (126MHz, CDCl 3 ):δ156.0,148.5, 147.4,139.8,138.7,136.2,131.7,129.9,129.5,129.1,128.8,128.6,128.3,127.5,125.7,124.4,119.4,21.8. ESI m / z[M+H] + 296.1;HRMS(ESI):calcd.for C 22 h 17 N[M+H] + 296.1434; found 296.1435.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

A kind of synthetic method of 2,4-diarylquinoline compound (II), described method is: compound shown in formula (I), oxidizing agent, organic solvent are mixed, be heated up to 60-80 ℃ and react 1-2h, Afterwards, the reaction solution is post-treated to obtain the product (II); the synthesis method of the present invention does not need to use metals and other additives, the operation is simple, the raw materials are easy to obtain, and the conditions are mild;

Description

technical field [0001] The invention relates to a method for synthesizing 2,4-diarylquinoline compounds. Background technique [0002] Quinoline and its derivatives are a class of alkaloids with a wide range of pharmacological and biological activities. Bacterial, antifungal (such as 2,4-diphenyl-6-fluoroquinoline, 2,4-diphenyl-6-chloroquinoline, 2,4-diphenyl-6-bromoquinoline, 2,4 -Diphenyl-6-methoxyquinoline has the effect of anti-Candida albicans and Cryptococcus neoformans), anti-cancer cells, etc. Therefore, the synthesis of 2,4-diarylquinoline compounds has important research significance. [0003] [0004] After reviewing the literature, it can be seen that the synthesis methods of 2,4-diphenylquinoline compounds mainly include the following types: 1) Combes reaction of aromatic amines and 1,3-diaryl-1,3-diketones; 2) 2 - Amino diaryl ketones with acetophenone or benzyl alcohols 3) Povarov reaction of aromatic amines, aldehydes and alkenes or alkynes; 4) cycliza...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/04C07D215/20C07D215/18C07D215/26C07D215/12
CPCC07D215/04C07D215/12C07D215/18C07D215/20C07D215/26
Inventor 程冬萍晏显航颜继忠
Owner ZHEJIANG UNIV OF TECH