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Environment-friendly synthesis method for 4(3H)-quinazolinone

A technology of quinazolinone and synthesis method is applied in the field of synthesis of 4-quinazolinone, and achieves the effects of simple operation, cheap and easily available raw materials, and easy industrial production.

Inactive Publication Date: 2014-03-05
CHENGDU UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

No related studies have been reported that do not require chemical oxidation reagents and catalysts

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 1 mmol anthranilamide, 1 mmol benzaldehyde, and 5 ml dimethyl sulfoxide solvent were sequentially added to the test tube, and the reaction was stirred at 120°C for 24 hours. After cooling, 10 ml of water was added to precipitate a white solid product, washed with 5 ml of petroleum ether, and the residual solvent was removed under reduced pressure to obtain 2-phenyl-4(3H)-quinazolinone with a yield of 97%. 2-Phenyl-4(3H)-quinazolinone: 1 H NMR (300 MHz, DMSO) δ 12.55 (s, 1H), 8.17 (t, J = 7.1 Hz, 3H), 7.83 (dd, J = 11.0, 4.1 Hz, 1H), 7.74 (d, J = 7.9 Hz , 1H), 7.66 –7.44 (m, 4H).

Embodiment 2

[0026] Experimental operation method is the same as embodiment 1. Using N,N-dimethylformamide instead of dimethyl sulfoxide, 2-phenyl-4(3H)-quinazolinone was obtained with a yield of 86%.

[0027]

Embodiment 3

[0029] Experimental operation method is the same as embodiment 1. The reaction temperature was lowered from 120°C in Example 1 to 100°C to obtain 2-phenyl-4(3H)-quinazolinone with a yield of 89%.

[0030]

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Abstract

The invention provides a method for synthesizing 2-substituted 4(3H)-quinazolinone by directly heating aldehyde and anthranilamide in air without using a catalyst. According to the synthesis method, air is taken as an oxidizing agent, aldehyde comprises compounds such as aromatic aldehyde, cinnamyl aldehyde and fatty aldehyde, recyclable dimethylsulfoxide is taken as a solvent, or excess recyclable aldehyde is taken as both a reactant and the solvent, due to heating, the aldehyde and anthranilamide react so as to obtain 2-substituted 4(3H)-quinazolinone compounds. The raw materials used by the synthesis method are easy to obtain; and the method is environment-friendly, is very simple to operate, and is applicable to industrial production.

Description

technical field [0001] The patent relates to the research fields of organic chemistry, organic chemical industry, and drug synthesis, specifically, the synthesis of 4(3H)-quinazolinone. [0002] Background technique [0003] 4(3H)-quinazolinone compounds have a wide range of pharmacological effects, and exhibit good pharmacological activities in anti-tumor, anti-hypertensive, anti-inflammatory, analgesic, bactericidal and other aspects. [0004] The 4(3H)-quinazolinones of pharmaceutical importance have many synthetic methods. [0005] For example, Croce et al. used l-aryl-4-dimethylamino-2-phenyl-1,3-diazo-1,3-butadiene and phenylisocyanate to reflux in toluene under nitrogen protection to obtain 2- Phenyl-4(3H)-quinazolinone with a yield of 70%-88% (Heterocycles, 1997, 45, 1309). One of the starting materials for Croce's method requires a multistep synthesis. [0006] Connolly et al. react HCl gas in the methanol solution of aromatic nitriles to obtain iminomethyl este...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/91C07D405/04C07D401/04C07D409/04
CPCC07D239/88C07D239/91C07D401/04C07D405/04C07D409/04
Inventor 曾庆乐裘德智魏海东
Owner CHENGDU UNIVERSITY OF TECHNOLOGY
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