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
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  • 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 me

Method used

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  • 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

Example Embodiment

[0072] Example 1: Synthesis of 2-phenylquinazoline

[0073]

[0074] Dissolve the compound of formula (II) in 100ml of solvent acetonitrile, then add the compound of formula (III), stir well, add CuCl, FeCl sequentially 3 , Ammonium chloride, KOH, 2,2’-bipyridine and TEMPO, make (II):(III):CuCl: FeCl 3 The molar ratio of :ammonium chloride:KOH:2,2'-bipyridine:TEMPO is 1:1:0.05:0.05:1:1:0.05:0.05, and the compound of formula (II) is 10 mmol.

[0075] In an air atmosphere, the above reaction system was allowed to react for 30 hours under stirring at 50°C. After the reaction, the solvent was removed from the mixture obtained after the reaction was completed 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),8.01-8.08(m,2H),7.72...

Example Embodiment

[0079] Example 2: Synthesis of 2-(4-fluorophenyl)quinazoline

[0080]

[0081] Dissolve the compound of formula (II) in 100ml of solvent THF, then add the compound of formula (III), stir evenly, add CuCl, FeBr sequentially 3 , Ammonium sulfate, KOH, 4,4’-bipyridine and TEMPO to make (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 10 mmol.

[0082] In an oxygen atmosphere, the above reaction system was allowed to react for 25 hours under stirring at 60°C. After the reaction, the solvent was removed from the mixture obtained after the reaction was completed 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=8.1...

Example Embodiment

[0086] Example 3: Synthesis of 2-(2-methylphenyl)quinazoline

[0087]

[0088] Dissolve the compound of formula (II) in 100ml of solvent DMF, then add the compound of formula (III), stir evenly, add CuCl, FeCl sequentially 3 , Ammonium acetate, KOH, 2,2’-bipyridine and TEMPO to make (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 10 mmol.

[0089] In an air atmosphere, the above reaction system was allowed to react for 20 hours under stirring at 70°C. After the reaction, the solvent was removed from the mixture obtained after the reaction was completed 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 oily substance with a yield of 84.3% and purity It was 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...

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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

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Application Information

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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
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