Synthesis of quinazoline ketone compounds

A quinazolinone and synthesis method technology, applied in the field of green chemical synthesis of quinazolinone compounds, can solve problems such as unrecyclable, serious environmental pollution, excessive catalyst, etc. The route is advanced and reasonable

Inactive Publication Date: 2009-05-13
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method requires an excessive amount of catalyst, cannot be recycled and applied mechanically, the yield is medium, and the environmental pollution is serious. Therefore, it is of great economic and social benefit to develop a green chemical synthesis method of quinazolinone compounds with high efficiency and environmental protection.

Method used

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  • Synthesis of quinazoline ketone compounds
  • Synthesis of quinazoline ketone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The ratio of the feed materials of o-amino-substituted benzamide, aldehyde, and zinc trifluoromethanesulfonate is 1:1:0.05, the o-amino-substituted benzamide is anthranilamide, and the aldehyde is benzaldehyde.

[0026] In a 150ml three-neck flask equipped with a thermometer, a reflux condenser and mechanical stirring, add 13.6g (0.1mol) of anthranilamide, 10.6g (0.1mol) of benzaldehyde, and 1.8g (5mmol) of zinc trifluoromethanesulfonate into nitroethane (30 mL), heated to 105° C., and reacted for 40 minutes. At the same time, HPLC was used to track and monitor (flow rate: 1.5ml / min, acetonitrile: water: acetic acid = 40:60:0.1). After the reaction was completed, cool to room temperature, add 20mL of water, and keep stirring for 10 minutes, the solid precipitated, and the insoluble matter was filtered out to obtain a crude product, which was recrystallized with ethanol to obtain a white solid of 2-phenyl-4(3H)-quinazoline Ketone 19.7g, yield 89%, purity 99.3%, melting ...

Embodiment 2

[0029] The ratio of the feed materials of o-amino-substituted benzamide, aldehyde, and scandium trifluoromethanesulfonate is 1:1:0.05, the o-amino-substituted benzamide is anthranilamide, and the aldehyde is benzaldehyde. 13.6 g (0.1 mol) of anthranilamide, 10.6 g (0.1 mol) of benzaldehyde, and 2.46 g (5 mmol) of scandium trifluoromethanesulfonate.

[0030] Others were the same as in Example 1 to obtain 20.2 g of the product 2-phenyl-4(3H)-quinazolinone, with a yield of 91%, a purity of 99.5%, a melting point of 238° C., and a recovery rate of scandium trifluoromethanesulfonate of 92.5%.

Embodiment 3

[0032] The ratio of the feed materials of o-amino-substituted benzamide, aldehyde, and lanthanum trifluoromethanesulfonate is 1:1:0.05, the amino-substituted benzamide is anthranilamide, and the aldehyde is benzaldehyde. 13.6 g (0.1 mol) of anthranilamide, 10.6 g (0.1 mol) of benzaldehyde, and 2.9 g (5 mmol) of lanthanum trifluoromethanesulfonate.

[0033] Others are the same as in Example 1 to obtain 20.4 g of the product 2-phenyl-4(3H)-quinazolinone, with a yield of 92%, a purity of 97.7%, a melting point of 237~238°C, and a recovery rate of lanthanum trifluoromethanesulfonate of 93.9% .

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Abstract

The invention provides a synthetic method for a quinazolinone compound. The structure of the quinazolinone compound is shown as formula (I). The method comprises the following steps: using o-amino benzamide compound shown in structural formula (II) and aldehyde shown in structural formula (III) as raw materials, using trifluoro mesylate as a catalyst, making the mixture reacted for 10 minutes to 24 hours in an inert organic solvent at a temperature of between 25 and 200 DEG C, and separating and purifying the reaction liquor after the reaction is finished to obtain the quinazolinone compound. The method has the advantages of high reaction yield up to more than 85 percent generally, advanced and reasonable process routes, mild reaction conditions, little dosage of the catalyst, reutilization, and substantially no three wastes.

Description

(1) Technical field [0001] The invention relates to a green chemical synthesis method of quinazolinone compounds. (2) Background technology [0002] Quinazolinone compounds are a class of compounds with good biological activity and pharmacological activity, widely used in the synthesis of pesticides and medicines, and have high practical value, including antihypertensive, antidiabetic, antiinflammatory, anticonvulsant, antibacterial and other pharmacological activities, not only some agricultural products contain the structure of quinazolinone, such as high-efficiency acaricide (Fenazaquin) and fluoroquinazole (Fluquinconazole), but also many drugs under research or developed contain this structure, such as sedative hypnotics Methaqualone (i.e., methaqualone), antitussive drug Chloroqualone and anticonvulsant drug Piriqualone, etc. In the prior art, traditional Lewis acid catalysts are used to prepare quinazolinone compounds. As proposed in Tetrahedron Letters 2004, 45, 34...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/36
CPCY02P20/584
Inventor 吴华悦陈久喜苏为科刘妙昌
Owner WENZHOU UNIVERSITY
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