Method for efficiently preparing quinazolinone compound

A technology for quinazolinones and compounds, which is applied in the field of efficient preparation of quinazolinone compounds, can solve the problems of inability to achieve substitution, high reaction temperature, limited product types of quinazolinone compounds, etc., and achieves less limitation of substrates , the reaction temperature is low, the effect of realizing the application value

Inactive Publication Date: 2016-05-04
JIANGXI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it can only be substituted at the second position of quinazolinone, but not on the nitrogen at the 3rd position, resulting in limited product types of quinazolinone compounds
In addition, a higher reaction temperature is required

Method used

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  • Method for efficiently preparing quinazolinone compound
  • Method for efficiently preparing quinazolinone compound
  • Method for efficiently preparing quinazolinone compound

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0020]

[0021] Add 0.2mmol 3-oxoquinazoline and 0.02mmol copper acetate to a clean 25mL reaction tube, and then add 0.6mmol benzaldehyde, 0.6mmol tert-butyl hydroperoxide (5.5 M in decane) and 2 mL of dichloromethane were reacted at 40 ° C for 4 hours, and detected by spotting on a silica gel plate; after the reaction, the reaction solution was extracted 3-5 times with ethyl acetate, and the organic phases were combined and dried with anhydrous sodium sulfate , the organic layer was concentrated and subjected to column chromatography to obtain pure benzoic acid-4-oxo-4-hydroquinazolin-3-ester as a pale yellow solid with a yield of 84%.

[0022] 1 HNMR (400MHz, CDCl 3 )δ8.34(d, J=8.2Hz, 1H), 8.21(d, J=7.9Hz, 2H), 8.15(s, 1H), 7.85–7.78(m, 2H), 7.74–7.67(m, 1H ),7.58–7.51(m,3H).

[0023] 13 CNMR (100MHz, CDCl 3 )δ163.0, 156.0, 147.1, 143.3, 135.1, 134.7, 130.6, 129.0, 128.1, 127.7, 127.1, 125.3, 123.6.

[0024] HRMS(ESI)calcdforC 15 h 10 N 2 o 3 [M+Na] + :289.0589...

example 2

[0028]

[0029] Add 0.2mmol 2-methyl-3-oxoquinazoline and 0.02mmol copper acetate to a clean 25mL reaction tube, and then add 0.6mmol benzaldehyde and 0.6mmol tert-butyl Hydrogen peroxide (5.5M in decane) and 2 mL of dichloromethane were reacted at 40°C for 4 hours, and detected by spotting on a silica gel plate; after the reaction, the reaction solution was extracted 3-5 times with ethyl acetate, and the organic phases were combined and used After drying over anhydrous sodium sulfate, the organic layer was concentrated and subjected to column chromatography to obtain pure benzoic acid-2-methyl-4-oxo-4-hydroquinazolin-3-ester as a pale yellow solid with a yield of 88%.

[0030] 1 HNMR (400MHz, CDCl 3 )δ8.27(d, J=8.0Hz, 1H), 8.23(d, J=8.1Hz, 2H), 7.82–7.76(m, 1H), 7.76–7.68(m, 2H), 7.60–7.53(m ,2H),7.53–7.46(m,1H),2.55(s,3H).

[0031] 13 CNMR (100MHz, CDCl 3 )δ162.8, 156.5, 152.3, 146.5, 135.1, 134.8, 130.6, 129.0, 127.2, 127.1, 126.8, 125.5, 122.3, 20.1.

[0032] HRMS...

example 3

[0034]

[0035] Add 0.2mmol 2-methyl-3-oxoquinazoline and 0.02mmol copper acetate into a clean 25mL reaction tube, and after pumping 3 times under a nitrogen atmosphere, add 0.6mmol p-tolualdehyde, 0.6mmol Tert-butyl hydroperoxide (5.5M in decane) and 2 mL of dichloromethane were reacted at 40°C for 4 hours, and detected by spotting on a silica gel plate; after the reaction, the reaction solution was extracted 3-5 times with ethyl acetate, and combined The organic phase was dried over anhydrous sodium sulfate, the organic layer was concentrated and subjected to column chromatography to obtain pure 4-methylbenzoic acid-2-methyl-4-oxo-4-hydroquinazolin-3-ester as a light yellow solid , yield 93%.

[0036] 1 HNMR (400MHz, CDCl 3 )δ8.27(d,J=8.0Hz,1H),8.12(d,J=8.2Hz,2H),7.81–7.75(m,1H),7.71(d,J=8.2Hz,1H,),7.51 –7.45(m,1H),7.36(d,J=8.1Hz,2H),2.54(s,3H),2.47(s,3H).

[0037] 13CNMR (100MHz, CDCl 3 )δ162.8, 156.6, 152.4, 146.6, 146.3, 134.7, 130.6, 129.8, 127.2, 127.0, 126.8, ...

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Abstract

The invention discloses a method for efficiently preparing a quinazolinone compound. The method adopts 3-oxygen quinazoline and aldehyde as substrates, copper salt as the catalyst and 5.5 M tert-butyl hydroperoxide in decane as the oxidizing agent, and the quinazolinone compound is obtained through reaction at the temperature of 40 DEG C in the nitrogen atmosphere according to the reaction formula (1) (please see the formula in the description). One-step reaction of 3-oxygen quinazoline and aldehyde is achieved, the quinazolinone compound is more directly and simply synthesized, reaction is more direct and simpler, the substrates are small in limitation, reaction temperature is low, time is short, and potential application value is better achieved.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for efficiently preparing quinazolinone compounds. Background technique [0002] Quinazolinones and their derivatives are widely used in the fields of medicine and pesticides because of their structural variability and high-efficiency and broad-spectrum biological activities. In the field of medicine, quinazolinone is mainly manifested in antibacterial, anti-tumor, anti-cancer, anti-AIDS and anti-tuberculosis, and also has quiet, antipyretic, anti-inflammatory, hypnotic, anti-convulsant, anti-Parkinson's syndrome, Regulating cardiovascular and cell and enzyme activity functions; in the research and development of pesticides, quinazolinones are mainly used in insecticide, bactericide, weed control and anti-virus. It has attracted people's interest and attention in the fields of chemistry, pharmacy and biology for many years, especially in recent years, it is one of the h...

Claims

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Application Information

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IPC IPC(8): C07D239/92C07D409/12C07D405/12C07D403/12
CPCC07D239/92C07D403/12C07D405/12C07D409/12
Inventor 王涛赵军锋范立文李柔田莹冯海燕黄阳妃
Owner JIANGXI NORMAL UNIVERSITY
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