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2-(2-iodoaryl)quinazoline compound and preparation method thereof

A quinazoline and iodo aryl technology is applied in the field of 2-quinazoline compounds and their preparation, which can solve the problems of miscellaneous products and difficult separation, and achieves convenient operation, easy column chromatography separation, and good application. effect of value

Active Publication Date: 2017-05-10
JIANGXI ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The traditional iodination reaction mechanism is a simple electrophilic substitution reaction, the reaction generally occurs at the electron-rich site, has the characteristics of a multi-site substitution reaction, and the reaction products are diverse, heterogeneous and difficult to separate

Method used

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  • 2-(2-iodoaryl)quinazoline compound and preparation method thereof
  • 2-(2-iodoaryl)quinazoline compound and preparation method thereof
  • 2-(2-iodoaryl)quinazoline compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0048]4-phenyl-2-p-tolylquinazoline (0.3mmol, 1.0eq), iodosuccinimide (NIS) (0.45mmol, 1.5eq), dichloro(pentamethylcyclopentadiene Base) rhodium (III) dimer (0.006mmol, 0.02equiv) and silver hexafluoroantimonate (0.024mmol, 0.08equiv) were added to the reaction test tube, and then the organic solvent 1,2-dichloroethane (2mL) was added React at 85°C for 1 hour. It was detected by TLC that the reaction was complete, cooled to room temperature, extracted with ethyl acetate and water, and the solvent was spin-dried, and the crude product was separated and purified by flash column chromatography with eluent (petroleum ether / ethyl acetate=30 / 1) to obtain pure Final product 2-(2-iodo-p-tolyl)-4-phenylquinazoline (2a).

[0049]

[0050] Yield: 87%; mp: 143-146°C;

[0051] 1 H NMR (400MHz, CDCl 3 ):δ8.20-8.18(m,2H),7.95-7.91(m,3H),7.90-7.88(m,1H),7.78(s,1H),7.65-7.57(m,4H),7.29(d ,J=8.00Hz,1H),2.37(s,3H);

[0052] 13 C NMR (100MHz, CDCl 3 ): δ168.0, 163.1, 151.5, 140.9, 140....

example 2

[0055] 2,4-diphenylquinazoline (0.3mmol, 1.0eq), NIS (0.45mmol, 1.5eq), dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer (0.006 mmol, 0.02 equiv) and silver hexafluoroantimonate (0.024 mmol, 0.08 equiv) were added to the reaction test tube, and then the organic solvent 1,2-dichloroethane (2 mL) was added to react at 85°C for 1.5 hours. It was detected by TLC that the reaction was complete, cooled to room temperature, extracted with ethyl acetate and water, and the solvent was spin-dried, and the crude product was separated and purified by flash column chromatography with eluent (petroleum ether / ethyl acetate=30 / 1) to obtain pure The final product is 2-(2-iodophenyl)-4-phenylquinazoline (2b).

[0056]

[0057] Yield: 81%; mp: 123-124℃;

[0058] 1 H NMR (400MHz, CDCl 3 ): δ8.20(d, J=8.4Hz, 2H), 8.03(d, J=8.0Hz, 1H), 7.97-7.93(m, 3H), 7.87(dd, J=1.6, 7.6Hz, 1H) ,7.67-7.63(m,1H),7.60-7.57(m,3H),7.51-7.47(m,1H),7.15-7.11(m,1H);

[0059] 13 C NMR (100MHz, CDCl 3 )...

example 3

[0062] Combine 2-(4-methoxyphenyl)-4-phenylquinazoline (0.3mmol, 1.0eq), NIS (0.45mmol, 1.5eq), dichloro(pentamethylcyclopentadienyl) Rhodium (III) dimer (0.006mmol, 0.02equiv) and silver hexafluoroantimonate (0.024mmol, 0.08equiv) were added to the reaction test tube, and then the organic solvent 1,2-dichloroethane (2mL) was added at 85°C Reaction 2.0 hours. It was detected by TLC that the reaction was complete, cooled to room temperature, extracted with ethyl acetate and water, and the solvent was spin-dried, and the crude product was separated and purified by flash column chromatography with eluent (petroleum ether / ethyl acetate=30 / 1) to obtain pure Final product 2-(2-iodo-4-methoxyphenyl)-4-phenylquinazoline (2c).

[0063]

[0064] Yield: 87%; mp: 185-186°C;

[0065] 1 H NMR (400MHz, CDCl 3 ):δ8.19-8.17(m,2H),7.94-7.91(m,3H),7.89-7.87(m,2H),7.58-7.56(m,4H),7.03(dd,J=2.4,8.4Hz ,1H),3.84(s,3H);

[0066] 13 C NMR (100MHz, CDCl 3 ): δ168.0, 162.7, 160.3, 151.5, 137....

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Abstract

The invention discloses a 2-(2-iodoaryl)quinazoline compound and a preparation method thereof. The 2-(2-iodoaryl)quinazoline compound is prepared by using 2-arylquinazoline as a reaction substrate through the process of carbon-hydrogen bond activation iodination with iodosuccinimide under the catalytic action of dichloro(pentamethylcyclopetadienyl)rhodium (III) dimer / silver hexafluoroantimonate, wherein the reaction temperature is 85 DEG C, and the reaction time is 1 to 2 hours. The preparation method provided by the invention has the advantages of high yield, excellent reaction chemical selectivity, mild reaction conditions, simple and convenient operation, low cost, less side reaction and high product purity; and the product disclosed by the invention is a novel compound, facilitates to separation and purification, is applicable to large-scale preparation, and has good application value and potential biological activity.

Description

technical field [0001] The invention relates to a preparation method of quinazoline compounds, in particular to 2-(2-iodoaryl)quinazoline compounds and a preparation method thereof. Background technique [0002] Quinazoline compounds exist in a large amount in natural products and have become a class of heterocyclic compounds with high research value because of their excellent pharmaceutical activity. They can be used as tyrosine kinase and cell phosphorylase inhibitors, and can also be used to prepare ligands for sedative drugs and receptors for GABA in the central nervous system (CNS). A large number of explorations and studies have shown that heterocyclic compounds containing quinazoline skeletons also have anti-tumor, anti-malarial, anti-virus, anti-spasmodic, anti-microbial, bactericidal and anti-inflammatory, insecticidal, and diabetes-treating effects. [0003] Since the discovery that quinazoline compounds have antimalarial effects in the 1940s, it has also been fou...

Claims

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Application Information

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IPC IPC(8): C07D239/74C07D239/91B01J31/28
CPCB01J31/28B01J2231/4277C07D239/74C07D239/91
Inventor 高伟龚春徐林初甘然黄文印
Owner JIANGXI ACAD OF FORESTRY
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