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Preparation method of 2-phenyl quinazolinone compound

A technology for phenylquinazolones and compounds, which is applied in the field of 2-phenylquinazolones and their preparations, and can solve problems such as difficult separation, expensive catalysts, and poor atom economy

Active Publication Date: 2021-10-29
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods are harsh and have the characteristics of difficult separation, expensive catalysts, and poor atom economy. The innovation of the present invention is to use the easily available 2-(benzylamino)benzamide as a raw material for the first time and use it under mild conditions. Metal-free catalysts, 2-phenylquinazolinone compounds can be obtained in high yields, with the advantages of green synthesis such as step economy and atom economy

Method used

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  • Preparation method of 2-phenyl quinazolinone compound
  • Preparation method of 2-phenyl quinazolinone compound
  • Preparation method of 2-phenyl quinazolinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: the synthetic method of 2-phenylquinazolin-4 (3H)-ketone

[0020]

[0021] Add 2-(benzylamino)benzamide (0.44mmol, 100mg), elemental iodine (0.04mmol, 11mg), and dimethyl sulfoxide (2ml) into the test tube in turn, and react at 130°C for 6h. After the end, the reaction solution Extracted 3 times with ethyl acetate, the combined organic phase was concentrated to dryness, and separated by column chromatography (petroleum ether: ethyl acetate=4:1) to obtain 2-phenylquinazolin-4(3H)-one, the yield : (91 mg, 91%). 1 H NMR (400MHz, DMSO-d 6 ): δ=12.54(s, 1H), 8.21-8.15(m, 3H), 7.88-7.82(m, 1H), 7.76(d, J=7.2Hz, 1H), 7.62-7.51(m, 4H); 13 C NMR (100 MHz, DMSO-d 6 ): δ=162.71, 152.78, 149.19, 135.09, 133.16, 131.88, 129.08, 128.23, 127.97, 127.07, 126.32, 121.43.

[0022] Replace catalyst and consumption, change reaction time, reaction solvent, when reaction temperature, reaction result is as follows:

[0023]

Embodiment 2

[0024] Embodiment 2: the synthetic method of 5-fluoro-2-phenylquinazolin-4 (3H)-ketone

[0025]

[0026] Add 2-(benzylamino)-6-fluorobenzamide (0.41mmol, 100mg), elemental iodine (0.04mmol, 11mg), and dimethyl sulfoxide (2ml) into the test tube in turn, and react at 130°C for 6h. , the reaction solution was extracted 3 times with ethyl acetate, the combined organic phases were concentrated to dryness, and separated by column chromatography (petroleum ether: ethyl acetate=4:1) to obtain 5-fluoro-2-phenylquinazoline-4( 3H)-ketone, yield: (89 mg, 77%). 1 H NMR (400MHz, DMSO-d 6 ): δ=12.59(s,1H),8.20-8.17(m,2H),7.83-7.78(m,1H),7.61-7.54(m,4H),7.26-7.25(m,1H); 13 C NMR (100 MHz, DMSO-d 6 ): δ=162.29, 160.0, 159.68, 153.73, 151.32, 135.60 (d, J = 10.7Hz), 132.67, 132.13, 129.80 (d, J = 75.6Hz), 124.02, 113.33 (d, J = 20.20Hz), 110.86(d,J=6.1Hz). 19 F NMR (376MHz, DMSO-d 6 )δ=111.45.

Embodiment 3

[0027] The synthetic method of embodiment 3:6-chloro-2-phenylquinazolin-4 (3H)-ketone

[0028]

[0029] Add 2-(benzylamino)-5-chlorobenzamide (0.38mmol, 100mg), elemental iodine (0.04mmol, 11mg), and dimethylsulfoxide (2ml) into the test tube in sequence, and react at 130°C for 6h. , the reaction solution was extracted 3 times with ethyl acetate, the combined organic phases were concentrated to dryness, and separated by column chromatography (petroleum ether: ethyl acetate=4:1) to obtain 6-chloro-2-phenylquinazoline-4( 3H)-ketone, yield: (82mg, 84%). 1 H NMR (400MHz, DMSO-d 6 ): δ=12.76(s,1H),8.19(d,J=7.2,2H),8.10(d,J=2.4,1H),7.90-7.87(m,1H),7.78(d,J=8.4Hz ,1H), 7.64-7.55(m,3H); 13 C NMR (100MHz, DMSO-d 6 ): δ=161.85, 153.38, 147.91, 135.16, 132.95, 132.07, 131.22, 130.15, 129.11, 128.32, 125.35, 122.69.

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Abstract

The invention relates to a preparation method of a 2-phenyl quinazolinone compound. The specific structure of the 2-phenyl quinazolinone compound is shown in a formula II. According to the method, a 2-(benzylamino) benzamide compound (I) is used as a raw material for reaction of the experimental model, and an elemental iodine catalyst and a solvent are added into a reaction reagent to obtain a target product (II); and the innovation point of the method is as follows: the easily available 2-(benzylamino) benzamide is used as the raw material for the first time, a metal-free catalyst is used under mild conditions, the 2-phenyl quinazolinone compound is obtained with higher yield, and the method has the advantages of green synthesis such as step economy and atom economy.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a 2-phenylquinazolinone compound and a preparation method thereof. Background technique [0002] Quinazolinones are nitrogen-containing benzoheterocyclic compounds, which belong to a large class of alkaloids. It has a wide range of applications in the fields of pesticides and medicine, and is particularly outstanding in the field of antibacterial, antiviral, antidiabetic, and antituberculosis, especially in the field of antitumor drug research. In traditional methods, quinazolinones are usually formed by coupling 2-aminobenzamides with aldehydes, carboxylic acids, and carboxyl halides. However, these methods are harsh and have the characteristics of difficult separation, expensive catalysts, and poor atom economy. The innovation of the present invention is to use the easily available 2-(benzylamino)benzamide as raw material for the first time under mild con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/91C07D471/04C07D235/18
CPCC07D239/91C07D471/04C07D235/18Y02P20/584Y02A50/30
Inventor 刘祈星文思妙妙崔晓峰周海峰赵蓉蓉
Owner CHINA THREE GORGES UNIV
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