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2-ferrocenyl-arylquinoline and preparation method thereof

A ferrocene-based and aryl-quinoline technology, applied in the field of materials, achieves the effects of a wide range of substrates, mild reaction conditions, and low prices

Inactive Publication Date: 2013-08-14
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the ferrocenyl-containing quinoline derivatives, especially the ferrocenyl-quinoline derivatives of the biaryl ring, have not been reported.

Method used

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  • 2-ferrocenyl-arylquinoline and preparation method thereof
  • 2-ferrocenyl-arylquinoline and preparation method thereof
  • 2-ferrocenyl-arylquinoline and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 2-ferrocenyl-arylquinoline, the general formula is:

[0024] The specific structure can be:

[0025]

[0026]

Embodiment 2

[0028] Compound (1) Preparation of 2-ferrocenyl-8-phenylquinoline: under the protection of high-purity nitrogen, add 1.0mmol acetylferrocene and 1.5mmol 6-bromo-o-hydroxymethyl to a 10ml Schlek reaction tube Aniline, 2.0mmol phenylboronic acid, 0.05mmol [Ir(cod)Cl] 2 , 0.05mmol palladium chloride, 0.15mmol triphenylphosphine, 3.0mmol sodium hydroxide and 5ml dioxane, replace the reaction tube with nitrogen for 3 times, then heat to 110°C with an oil bath under magnetic stirring, and reflux for 16 Hour.

[0029] The oil bath was removed, and the water bath was lowered to room temperature; 3ml of water was added to the reaction solution, extracted three times with 5ml of dichloromethane, the organic phases were combined and washed with anhydrous MgSO 4 Dry for 30 minutes, filter, and concentrate the filtrate with a rotary evaporator. The concentrated residue is separated by silica gel column chromatography using dichloromethane as a developing solvent to obtain pure product 1 w...

Embodiment 3

[0031] Compound (2) Preparation of 2-ferrocenyl-6-phenylquinoline: under the protection of high-purity nitrogen, add 1.0mmol acetylferrocene and 1.0mmol 4-bromo-o-hydroxymethyl to a 10ml Schlek reaction tube Aniline, 1.0mmol phenylboronic acid, 0.01mmol [Ir(cod)Cl] 2 , 0.01mmol palladium acetate, 0.05mmol triphenylphosphine, 1.0mmol potassium hydroxide and 5ml dioxane, replace the reaction tube with nitrogen for 3 times, then heat to 110°C with an oil bath under magnetic stirring, and reflux for 48 hours .

[0032] The oil bath was removed, and the water bath was lowered to room temperature; 3ml of water was added to the reaction solution, extracted three times with 5ml of dichloromethane, the organic phases were combined and washed with anhydrous MgSO 4 Dry for 30 minutes, filter, and the filtrate is concentrated by a rotary evaporator. The concentrated residue is separated by silica gel column chromatography using dichloromethane as a developing solvent to obtain pure produ...

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PUM

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Abstract

The invention discloses 2-ferrocenyl-arylquinoline which has the general formula shown in the specification, wherein Aryl is the aryl and is connected to the position 5, 6, 7 or 8 of quinoline. A preparation method of 2-ferrocenyl-arylquinoline comprises the following steps: adding acetylferrocene, bromo-o-hydroxyl methyl aniline, Aryl-B(OH)2, [Ir(cod)Cl]2, palladium salt, triphenylphosphine and alkali into the organic solvent, heating and refluxing for reacting under inert gas shielding, and separating and purifying to obtain the product after the reaction is ended. The provided 2-ferrocenyl-arylquinoline compound has the dual characteristics of ferrocene and arylquinoline and can be applied to the fields of electrochemistry, biochemistry, materials chemistry and organocatalysis.

Description

technical field [0001] The invention belongs to the technical field of materials, and in particular relates to a class of 2-ferrocenyl-arylquinoline compounds, and also relates to a preparation method of the compounds. Background technique [0002] Quinoline and its derivatives have biological and pharmacological activities such as sterilization, antibacterial, antiallergic, and antitumor, and are widely used in medicine, pesticide production, and functional materials. Quinoline derivatives were first extracted from coal tar. The technical route is complex and the product types are limited. Some important quinoline derivatives cannot be obtained by this method. [0003] In recent years, on the basis of traditional synthetic routes, technicians have developed a new synthetic route using transition metal complexes as catalysts, which is currently the most researched and most promising method. For example, Au can catalyze the three-component coupling reaction of aldehydes, ami...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
Inventor 李红梅李晓冬徐晨肖志强郝新奇
Owner LUOYANG NORMAL UNIV
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