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A kind of method for efficiently preparing quinazolinone compound

A technology for quinazolinone and compounds, which is applied in the field of efficient preparation of quinazolinone compounds, can solve the problems of inability to replace, high reaction temperature, and limited product types of quinazolinone compounds, and achieve small substrate limitations , the reaction temperature is low, and the effect of realizing the application value

Inactive Publication Date: 2018-09-18
JIANGXI NORMAL UNIV
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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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  • A kind of method for efficiently preparing quinazolinone compound
  • A kind of method for efficiently preparing quinazolinone compound
  • A kind of 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 H NMR (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 C NMR (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) calcd for C 15 h 10 N 2 o 3 [M+Na] + :28...

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 H NMR (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 C NMR (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] HR...

example 3

[0034]

[0035] Add 0.2mmol 2-methyl-3-oxoquinazoline and 0.02mmol copper acetate to a clean 25mL reaction tube, and then add 0.6mmol p-tolualdehyde, 0.6 Mmol tert-butyl hydroperoxide (5.5M in decane) and 2mL 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, The organic phases were combined and 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, light yellow Solid, 93% yield.

[0036] 1 H NMR (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] 13C NMR (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, 122.6, 122.4, 21.9, 20.1.

[0038] HRMS (ESI) calcd...

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Abstract

The invention discloses a method for efficiently preparing quinazolinone compounds, using 3-oxyquinazoline and aldehyde as substrates, copper salt as a catalyst, and 5.5M tert-butyl hydroperoxide in decane as an oxidant , react under nitrogen atmosphere and 40 DEG C to obtain quinazolinone compound, and its reaction formula is (1), the present invention realizes the one-step reaction utilizing 3-oxoquinazoline and aldehyde, and more directly and concisely synthesizes quinazolinones Compounds, the reaction is more direct and concise, the substrate limitation is small, the reaction temperature is low, and the reaction time is short, and its potential application value can be better realized.

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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Patent Type & Authority Patents(China)
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 UNIV
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