A kind of synthetic method of quinazolinone aromatic compound

A quinazolinone aromatic and synthesis method technology, applied in the direction of organic chemistry, can solve the problems of harsh reaction conditions, narrow substrate range, and long reaction time, and achieve short reaction time, wide substrate range, and green post-treatment Effect

Active Publication Date: 2017-05-03
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are many problems, such as: narrow substrate range, harsh reaction conditions, long reaction time, many by-products, low yield, need strong acid and other non-green environmental protection reagents, etc.

Method used

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  • A kind of synthetic method of quinazolinone aromatic compound
  • A kind of synthetic method of quinazolinone aromatic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of 2-phenyl-3-phenethylquinazolin-4(3H)-one

[0022] Add 0.25mmol of 2-phenylindole, 0.5mmol of phenethylamine, 0.0125mmol of cuprous bromide, and 2.0mL of N-methylpyrrolidone into a 10mL reaction tube, place it in an oil bath at 80°C, and react under the protection of oxygen 20h. Stop the reaction and cool to room temperature. The reaction solution was diluted with dichloromethane, extracted three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 After drying, filtering, and separation by column chromatography, 77.5 mg of the target product was obtained, with a yield of 96%. The NMR characterization of this compound is as follows: 1 HNMR (400MHz, DMSO-d 6 ):δ8.24(d,J=8.0Hz,1H),7.94–7.80(m,1H),7.68(d,J=8.1Hz,1H),7.63–7.48(m,6H),7.25–7.12( m,3H),6.92–6.72(m,2H),4.1(t,J=7.8Hz,2H),2.83(t,J=7.8Hz,2H); 13 C NMR (100MHz, DMSO-d 6 )δ161.1, 155.9, 146.8, 137.8, 135.2, 134.5, 129.6, 128.5, 128.3 (overlapped), 127.9, 127.2, 127.0, 126...

Embodiment 2

[0024] Preparation of 2-phenyl-3-phenethylquinazolin-4(3H)-one

[0025] Add 0.25mmol of 2-phenylindole, 0.5mmol of phenethylamine, 0.0125mmol of cuprous bromide, and 2.0mL of N, N dimethylformamide into a 10mL reaction tube, place in an oil bath at 80°C, and oxygen Reaction under protection for 20h. Stop the reaction and cool to room temperature. The reaction solution was diluted with dichloromethane, extracted three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dried, filtered, and separated by column chromatography to obtain 77.5 mg of the target product with a yield of 86%.

Embodiment 3

[0027] Preparation of 2-phenyl-3-phenethylquinazolin-4(3H)-one

[0028] Add 0.25mmol of 2-phenylindole, 0.5mmol of phenethylamine, 0.0125mmol of cuprous bromide, and 2.0mL of N, N dimethylacetamide into a 10mL reaction tube, place in an oil bath at 80°C, and oxygen Reaction under protection for 20h. Stop the reaction and cool to room temperature. The reaction solution was diluted with dichloromethane, extracted three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 After drying, filtering, and separation by column chromatography, 77.5 mg of the target product was obtained, with a yield of 84%.

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Abstract

The invention discloses a synthetic method of a quinazolinone aromatic compound. The synthetic method comprises the following steps: dissolving 2-aryl indole, organic amine / inorganic amine and cuprous bromide in an organic solvent; carrying out reaction for 20-30 hours at 60-120 DEG C in the presence of oxygen; and separating and purifying to obtain the quinazolinone aromatic compound. According to the synthetic method, the raw materials are easily available and the yield is high (99%); the synthetic method is mild in reaction condition, short in reaction time, wide in primer range, strong in reaction specificity and simple and green in post-treatment.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of quinazolinone aromatic compounds. Background technique [0002] Quinazolinone aromatic compounds are a class of widely used organic synthesis intermediates. It has important application value in daily commodities, pharmaceutical production, organic synthesis, and agricultural protection. Chemists have been trying in recent years. Some systems have been successfully applied to this reaction, and some research results have been obtained. However, there are many problems, such as: narrow substrate range, harsh reaction conditions, long reaction time, many by-products, low yield, and the need for non-green and environmentally friendly reagents such as strong acids, etc. Contents of the invention [0003] The purpose of the present invention is to overcome the defects of the prior art and provide a synthetic method of quinazolinone arom...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/91
CPCC07D239/91
Inventor 崔秀灵冯亚栋李玉东
Owner HUAQIAO UNIVERSITY
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