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The synthetic method of 1-aryl benzo [f] quinoline derivatives

A synthetic method and derivative technology, applied in the direction of organic chemistry, can solve the problems of difficult separation and operation of the target product, long reaction process, and easy volatility, and achieve good industrial application prospects, simple and safe post-processing, and mild reaction conditions.

Inactive Publication Date: 2011-11-30
NORTHWEST NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although these methods have high yields, there are still many problems: (1) organic solvents are used, and most of the traditional organic solvents are expensive, volatile, flammable, toxic, difficult to recycle, pollute the environment, and target products. Problems such as difficulty in separation operation (2) need to add catalyst, there are also problems such as high price, troublesome preparation, environmental pollution; (3) some reactions need to prepare intermediates, the operation is cumbersome, and the reaction process is long

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  • The synthetic method of 1-aryl benzo [f] quinoline derivatives

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Experimental program
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Embodiment 1

[0022] Embodiment one, Synthesis of 1-aryl-1,2-dihydrobenzo[f]quinolin-3(4H)-one

[0023] Add 2 mmol (0.212 g) of benzaldehyde, 2 mmol (0.286 g) of 2-naphthylamine, 2 mmol (0.288 g) of Meldrum acid, and 5 mmol (2 g) of PEG-400 into a 50 mL round bottom flask, and react at 100 °C After 20 h, the whole reaction process was tracked by thin layer chromatography (TCL); the reaction solution was obtained after the reaction was complete. Let the reaction solution stand for about 2 hours, let the reaction solution cool down, then add 30mL of water to it and stir to dissolve the reaction solvent PEG-400 in water, and let it stand overnight to fully precipitate the target product, filter, wash with water, and suction filter , the crude product was recrystallized with 95% absolute ethanol to obtain the target product—1-aryl-1,2-dihydrobenzo[f]quinolin-3(4H)-one. The yield was 80%.

[0024] 1 H NMR (400 MHz, DMSO- d 6) δ : 2.64 (d, J =16.0 Hz, 1H, CH 2 ), 3.17 (dd, J =16.0, 7....

Embodiment 2

[0025] Embodiment two, 1-(4-Chlorophenyl)-1,2-dihydrobenzo[ f ]quinoline-3(4 H )-ketone synthesis

[0026] In a 50 mL round bottom flask, add 2 mmol (0.281 g) of 4-chlorobenzaldehyde, 2 mmol (0.286 g) of 2-naphthylamine, 2 mmol (0.288 g) of Meldrum acid, 5 mmol (2 g) of PEG-400 at 90 The reaction was carried out at ℃ for 16 hours, and the whole reaction process was tracked by thin layer chromatography (TCL); the reaction liquid was obtained after the reaction was complete. Let the reaction solution stand for about 2 hours, let the reaction solution cool down, then add 30mL of water to it and stir to dissolve the reaction solvent PEG-400 in water, and let it stand overnight to fully precipitate the target product, filter, wash with water, and suction filter , the crude product was recrystallized with 95% absolute ethanol to obtain the target product——1-(4-chlorophenyl)-1,2-dihydrobenzo[ f ]quinoline-3(4 H )-ketone. The yield was 84%.

[0027] 1 H NMR (400 MHz, DMSO- d...

Embodiment 3

[0028] Embodiment three, 1-(2,4-dichlorophenyl)-1,2-dihydrobenzo[ f ]quinoline-3(4 H )-ketone synthesis

[0029]In a 50 mL round bottom flask, add 2 mmol (0.35 g) of 2,4-dichlorobenzaldehyde, 2 mmol (0.286 g) of 2-naphthylamine, 2 mmol (0.288 g) of Meldrum acid, 4 mmol (1.6 g) of PEG- 400, react at 95°C for 14h, and track the whole reaction process with thin-layer chromatography (TCL); the reaction solution is obtained after the reaction is complete. Let the reaction solution stand for about 2 hours, let the reaction solution cool down, then add 30mL of water to it and stir to dissolve the reaction solvent PEG-400 in water, and let it stand overnight to fully precipitate the target product, filter, wash with water, and suction filter , the crude product was recrystallized with 95% absolute ethanol to obtain the target product——1-(2,4-dichlorophenyl)-1,2-dihydrobenzo[ f ]quinoline-3(4 H )-ketone. The yield was 81%.

[0030] 1 H NMR (400MHz, DMSO- d 6) δ : 2.54 (d, ...

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Abstract

The invention discloses a method for synthesizing 1-arylbenzo[f]quinoline derivatives, which belongs to the technical field of chemical synthesis. The method is to use aromatic aldehyde, 2-naphthylamine and McFarlandic acid as raw materials, polyethylene glycol PEG400 as solvent and catalyst, reflux reaction at 80~100°C for 14~20h, suction filtration, washing with water, and the obtained crude product is passed through The target product was obtained by recrystallization from absolute ethanol. The present invention synthesizes a series of 1-arylbenzo[f]quinoline derivatives through three-component one-pot reaction, which has the advantages of mild reaction conditions, simple synthesis process, high yield and low cost; environment-friendly, non-toxic , post-processing is simple and safe, and meets the requirements of green chemistry.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry and relates to a synthesis method of 1-arylbenzo[f]quinoline derivatives. Background technique [0002] Benzoquinoline derivatives have biological and pharmacological activities, such as antibacterial, antihypertensive, antimalarial and antiviral activities. 1-Arylbenzo[f]quinoline derivatives have photochemical activity in addition to the above-mentioned biological activities. Therefore, it has broad application prospects in many aspects such as material science and life science. [0003] The structural formula of 1-aryl benzo [f] quinoline derivatives is as follows: [0004] [0005] where Ar = C 6 h 5 , 4-ClC 6 h 4 , 2,4-Cl 2 C 6 h 3 , 4-BrC 6 h 4 , 4-FC 6 h 4 , 4-CH 3 OC 6 h 4 , 2-NO 2 C 6 h 4 , 3-NO 2 C 6 h 4 or 4-NO 2 C 6 h 4 . [0006] Generally, there are one-step and two-step methods for synthesizing 1-arylbenzo[f]quinoline derivatives. The one-...

Claims

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Application Information

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IPC IPC(8): C07D221/08
Inventor 王喜存王雪梅权正军张彰
Owner NORTHWEST NORMAL UNIVERSITY
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