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Quinoline triarylamine and preparation method thereof

A technology of quinolinyl triarylamine and triarylamine, which is applied in the field of catalytic organic synthesis, can solve the problems of low reaction efficiency, difficult synthesis, and difficult oxidation addition of metal catalysts, etc., and achieves the effect of high yield and easy operation

Active Publication Date: 2019-08-09
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Triarylamines play an extremely important role, but their synthesis is not easy
However, for aromatic hydrocarbons with large steric hindrance, the oxidative addition of metal catalysts is not easy due to the large steric hindrance effect, making the reaction efficiency low

Method used

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  • Quinoline triarylamine and preparation method thereof
  • Quinoline triarylamine and preparation method thereof
  • Quinoline triarylamine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0024] Add 1 magnetic stir bar, 8-amino-5-thiophenylquinoline (0.3mmol), 9-(4-bromophenyl)carbazole (0.6mmol), and nickel chloride (0.06mmol) to the 10mL reaction tube. ), potassium carbonate (1.2 mmol), vacuum and fill with nitrogen 3 times, add tetrahydrofuran (2 mL) under nitrogen atmosphere, and react at 100°C for 24 hours. After the reaction, it was quenched by adding saturated aqueous ammonium chloride solution, extracted with ethyl acetate, dried, concentrated, and separated by column chromatography to obtain N,N-bis(4-(9H-carbazol-9-yl)phenyl)- The yield of 5-(phenylthio)-8-aminoquinoline was 97%.

preparation example 2

[0026] Add 1 magnetic stir bar, 8-aminoquinoline (0.3mmol), 9-(4-bromophenyl)carbazole (0.6mmol), nickel bromide (0.06mmol), potassium carbonate (1.2mmol) into the 10mL reaction tube. mmol), vacuum and fill with nitrogen 3 times, add tetrahydrofuran (2mL) under nitrogen atmosphere, and react at 100°C for 24 hours. After the reaction, it was quenched by adding saturated aqueous ammonium chloride solution, extracted with ethyl acetate, dried, concentrated, and separated by column chromatography to obtain N,N-bis(4-(9H-carbazol-9-yl)phenyl)- The yield of 8-aminoquinoline was 95%.

preparation example 3

[0028] Add 1 magnetic stir bar, 8-amino-6-methoxyquinoline (0.3mmol), 9-(4-bromophenyl)carbazole (0.6mmol), nickel fluoride (0.03mmol) to the 10mL reaction tube ), potassium carbonate (0.9 mmol), evacuated and filled with nitrogen 3 times, added tetrahydrofuran (2 mL) under nitrogen atmosphere, and reacted at 100°C for 24 hours. After the reaction, it was quenched by adding saturated aqueous ammonium chloride solution, extracted with ethyl acetate, dried, concentrated, and separated by column chromatography to obtain N,N-bis(4-(9H-carbazol-9-yl)phenyl) -6-(Methoxy)-8-aminoquinoline, the yield was 93%.

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Abstract

The invention discloses quinoline triarylamine and a preparation method thereof. A substituted 8-aminoquinoline compound (I) and a carbazole compound (II) are used as substrates, and a nickel catalystwith the mole fraction of 1% to 30% (relative to a primary amine compound I, the same below) and 2-5 molar equivalents of alkali are added, 2 mL of an organic solvent serves as a solvent, and the reaction mixture is stirred for reaction at 25-160 DEG C under a nitrogen atmosphere for 1-48 hours, a saturated ammonium chloride solution is added for quenching after the reaction is complete, extraction is executed with a polar organic solvent, anhydrous sodium sulfate or anhydrous magnesium sulfate is added for drying, and the target product triarylamine compound (III) is obtained through concentration by a rotary evaporator and separation by column chromatography to obtain. The method has the advantages of cheap catalyst, high yield, simple and convenient operation, no generation of harmfulbyproducts and the like, and has certain feasibility for realizing industrial production. The synthesized quinoline triarylamine compound can be converted into various functional molecules through various cascade reactions or cross coupling reactions, and has the potential application value in the fields of biomedicine and materials.

Description

[0001] 【Technical Field】 [0002] The invention belongs to the field of catalytic organic synthesis, and specifically relates to a novel method for preparing quinolinyl triarylamine compounds by using substituted 8-aminoquinoline compounds and substituted carbazole compounds under transition metal nickel as a catalyst. method. This method uses 8-aminoquinoline compounds with different substituents and carbazole compounds with different substituents as the main raw materials, transition metal nickel as catalyst, polar organic solvent as solvent, and inorganic salt as base. 2 Reaction at 25-160°C for 1-48h under an atmosphere to prepare quinolinyltriarylamine compounds in higher yield. [0003] 【Background technique】 [0004] Triarylamine compounds are an important class of compounds, especially triarylamine compounds with large steric hindrance and large conjugated systems have a wide range of applications in the fields of optoelectronic materials, pharmaceutical intermediates, and or...

Claims

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Application Information

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IPC IPC(8): C07D401/14
CPCC07D401/14
Inventor 邱仁华严明盼朱龙志神户宣明
Owner HUNAN UNIV
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