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Method of synthesizing quinazolinone-structured compound

A quinazolinone and compound technology, which is applied in the field of synthesizing compounds with quinazolinone structure, can solve the problems of uneconomical reaction process, difficult separation and purification, and environmental protection

Inactive Publication Date: 2016-07-06
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
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  • Application Information

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Problems solved by technology

The traditional method is to condense aldehydes with anthranilamide. This method usually requires metered or excessive oxidants such as potassium permanganate, cuprous chloride, molecular iodine, etc. The reaction process is uneconomical, not environmentally friendly, and the product is complicated. Separation Difficult to purify

Method used

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  • Method of synthesizing quinazolinone-structured compound

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Experimental program
Comparison scheme
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Embodiment 1

[0025] 0.5 mmol anthranilamide, 1.5 mmol benzyl alcohol, 0.05 mmol α-MnO 2 1. Add 2 ml of chlorobenzene into the pressure bottle, then add 1 mmol of tert-butyl hydroperoxide, and react for 16 hours at 80°C under normal pressure. The reaction product is analyzed by GC, and the yield of the compound with quinazolinone structure is 83%. . Product NMR see figure 1 .

Embodiment 2

[0027] 0.5 mmol anthranilamide, 1.5 mmol benzyl alcohol, 0.05 mmol β-MnO 2 1. Add 2 ml of acetonitrile into the pressure bottle, then add 1 mmol of tert-butyl hydroperoxide, and react for 12 hours at 80°C under normal pressure. The reaction product is analyzed by GC, and the yield of the compound with quinazolinone structure is 73%.

Embodiment 3

[0029] 0.5 mmol anthranilamide, 1.5 mmol benzyl alcohol, 0.05 mmol MnO 2 (Ar-150-2h), 2 milliliters of tetrahydrofuran were added to the pressure bottle, and then 1 mmol of cyclohexyl hydroperoxide was added, and the reaction was carried out at 90°C under normal pressure for 16 hours. The reaction product was analyzed by GC. The quinazolinone structure Compound yield 53%.

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Abstract

A method of synthesizing a quinazolinone-structured compound includes the steps of adding an alcohol and amine as substrates in a liquid solvent with a peroxide as an oxidizing agent, and performing a reaction under the effects of a catalyst at 0-150 DEG C for 10-20 h to synthesize the quinazolinone-structured compound, wherein the catalyst includes metal oxides and / or metal oxides having a defect locus, and the metal oxides include one or more than two of [alpha]-MnO2, [beta]-MnO2, [delta]-MnO2, Mn2O3, Mn3O4, Fe2O3, V2O5, Co3O4 or MoO3, and the metal oxides having the defect locus is MnO2 treated in the presence of argon gas. The method, under a mild condition, is used for synthesizing the quinazolinone-structured compound at high efficiency and selectivity. The method has mild operation conditions and reaches 96% in yield of the quinazolinone-structured compound.

Description

technical field [0001] The invention belongs to the field of chemistry and chemical engineering, and in particular relates to a method for synthesizing a compound with a quinazolinone structure. Background technique [0002] Quinazolinone and its derivatives exist in a wide variety of natural products and synthetic drugs. Because of their quinazolinone structure, they have important biological activities and are of great value in medicinal chemistry. Some drugs such as hypolipidemic, anti-inflammatory, anti-convulsant, anti-ulcer, anti-cancer drugs, etc. have this structure. It is currently reported that some compounds with this structure have important medical value in the treatment of pulmonary tuberculosis. [0003] Due to its important applications, the development of new methods to synthesize compounds with quinazolinone structure has been attracting people's attention. The traditional method is to condense aldehydes with anthranilamide. This method usually requires m...

Claims

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Application Information

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IPC IPC(8): C07D239/91C07D239/90
Inventor 王峰张哲徐杰王敏
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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