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
View PDF4 Cites 12 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

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]

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap