Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesizing aryl or heteroaryl substituted quinazoline compound

A synthesis method and compound technology, which is applied in the synthesis of aryl or heteroaryl substituted quinazoline compounds and the synthesis of nitrogen-containing condensed ring compounds, and can solve the problems of high price, difficult synthesis of o-aminobenzylamine, and rare raw materials

Active Publication Date: 2013-12-25
WENZHOU UNIVERSITY
View PDF6 Cites 23 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] Although there are multiple synthetic methods of quinazoline derivatives as described above in the prior art, there are more or less defects in these methods, such as raw materials are difficult to synthesize (such as o-aminobenzylamine is difficult to synthesize, expensive), use of noble metal catalysts, etc.

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

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing aryl or heteroaryl substituted quinazoline compound
  • Method for synthesizing aryl or heteroaryl substituted quinazoline compound
  • Method for synthesizing aryl or heteroaryl substituted quinazoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1: the synthesis of 2-phenylquinazoline

[0073]

[0074] Dissolve the compound of formula (II) in 100ml solvent acetonitrile, then add the compound of formula (III), after stirring evenly, add CuCl, FeCl in sequence 3 , ammonium chloride, KOH, 2,2'-bipyridine and TEMPO, so that (II):(III):CuCl:FeCl 3 : Ammonium chloride: KOH: 2,2'-bipyridine: TEMPO is 1:1:0.05:0.05:1:1:0.05:0.05 in molar ratio, wherein the compound of formula (II) is 10mmol.

[0075] In an air atmosphere, the above reaction system was reacted for 30 hours under stirring at 50°C. After the reaction, the solvent was removed from the mixture obtained after the reaction with a rotary evaporator, and the residue was purified by 200-300 mesh silica gel column chromatography to obtain the target product as a solid, with a yield of 92.8% and a purity of 99.1%. (HPLC).

[0076] Melting point: 97-98°C.

[0077] NMR: 1 H NMR (DMSO-d 6 ,500MHz)δ9.71(s,1H),8.56-8.59(m,2H),8.17(d,J=8.0Hz,1H),8.01...

Embodiment 2

[0079] Embodiment 2: the synthesis of 2-(4-fluorophenyl) quinazoline

[0080]

[0081] Dissolve the compound of formula (II) in 100ml solvent THF, then add the compound of formula (III), stir well, then add CuCl, FeBr in sequence 3 , ammonium sulfate, KOH, 4,4'-bipyridine and TEMPO, so that (II):(III):CuCl:FeBr 3 : Ammonium sulfate: KOH: 4,4'-bipyridine: TEMPO is 1:1.5:0.1:0.1:2:2:0.1:0.1 in molar ratio, wherein the compound of formula (II) is 10mmol.

[0082] In an oxygen atmosphere, the above reaction system was reacted for 25 hours under stirring at 60°C. After the reaction, the solvent was removed from the mixture obtained after the reaction with a rotary evaporator, and the residue was purified by 300-400 mesh silica gel column chromatography to obtain the target product as a solid, with a yield of 89.4% and a purity of 99.2%. (HPLC).

[0083] Melting point: 135-137°C.

[0084] NMR: 1 H NMR (CDCl 3,500MHz)δ9.43(s,1H),8.60-8.64(m,2H),8.06(d,J=8.3Hz,1H),7.89(t,J=8....

Embodiment 3

[0086] Embodiment 3: the synthesis of 2-(2-tolyl) quinazoline

[0087]

[0088] Dissolve the compound of formula (II) in 100ml solvent DMF, then add the compound of formula (III), stir well, then add CuCl, FeCl in sequence 3 , ammonium acetate, KOH, 2,2'-bipyridine and TEMPO, so that (II):(III):CuCl:FeCl 3 : Ammonium acetate: KOH: 2,2'-bipyridine: TEMPO is 1:2:0.2:0.2:3:3:0.15:0.15 in molar ratio, wherein the compound of formula (II) is 10mmol.

[0089] In an air atmosphere, the above reaction system was reacted for 20 hours under stirring at 70°C. After the reaction ended, the solvent was removed from the mixture obtained after the reaction with a rotary evaporator, and the residue was purified by 400-500 mesh silica gel column chromatography to obtain the target product as a viscous oil, with a yield of 84.3%, a purity of 98.8% (HPLC).

[0090] NMR: 1 H NMR (CDCl 3 ,500MHz)δ9.50(s,1H),8.10(d,J=8.3Hz,1H),7.89-7.94(m,2H),7.77(d,J=7.6Hz,1H),7.63(t,J =7.6Hz,1H),7.45(t,J...

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

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to View More

Abstract

The invention provides a method for synthesizing an aryl or heteroaryl substituted quinazoline compound. According to the method, a copper compound and an iron compound serve as a bicomponent catalyst, and o-aminobenzyl alcohol and an aldehyde compound are enabled to react in the presence of an ammonium compound, alkali, organic ligands and TEMPO (Tetramethylpiperidine Oxide), thereby obtaining the aryl or heteroaryl substituted quinazoline compound. According to the method provided by the invention, the operation is simple, and the yield and purity of the product are high, so that the method has good industrial application potential.

Description

technical field [0001] The invention provides a synthesis method of nitrogen-containing condensed ring compounds, more specifically, provides a synthesis method of aryl or heteroaryl substituted quinazoline compounds, belonging to the field of synthesis of organic nitrogen-containing heterocyclic compounds. Background technique [0002] Nitrogen-containing heterocyclic compounds generally have certain biological activities and unique properties, so they have a wide range of applications and research prospects in the fields of medicine, pesticides, and organic luminescence. As a kind of nitrogen-containing heterocyclic compounds, quinazoline compounds have many excellent biological activities and optical activities, and can be widely used in medicine, sterilization, insecticide, antiviral, insecticidal, antiviral, anti-inflammatory, antihypertensive In the fields of anti-tuberculosis, organic electroluminescence, etc., researchers have put a lot of effort into the search and ...

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
IPC IPC(8): C07D239/74C07D409/04C07D405/04
Inventor 吴华悦陈久喜刘妙昌丁金昌高文霞黄小波
Owner WENZHOU UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com