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2-biaryl-6-arylquinazoline and preparation method thereof

An arylquinoline and biaryl technology, which is applied in the field of 2-biaryl-6-arylquinoline compounds and achieves the effects of mild reaction conditions, high yield and wide substrate range

Inactive Publication Date: 2015-04-01
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, aryl-substituted quinoline derivatives, especially biaryl-substituted quinoline derivatives, have rarely been reported.

Method used

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  • 2-biaryl-6-arylquinazoline and preparation method thereof
  • 2-biaryl-6-arylquinazoline and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 2-biaryl-6-arylquinoline compounds, the general formula is:

[0023] The specific structure can be:

[0024]

Embodiment 2

[0027] The preparation of 2-biphenyl-6-phenylquinoline, that is, compound (1): under the protection of inert gas (such as high-purity nitrogen), pour 10ml of Schlek reaction tube (a kind of glass commonly used in anhydrous and oxygen-free operation) instrument) by adding 1.0mmol p-bromoacetophenone, 1.2mmol 2-amino-5-bromobenzyl alcohol, 2.0mmol phenylboronic acid, 0.01mmol RuCl 2 (DMSO) 4 , 0.02mmol palladium acetate, 0.05mmol triphenylphosphine, 2.0mmol 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 8 hours . 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 and filter; the filtrate is concentrated with a rotary evaporator, and the concentrated solid...

Embodiment 3

[0029] The preparation of 2-(4-methylbiphenyl)-6-(4-methylphenyl)quinoline, that is, compound (2): under the protection of an inert gas (such as high-purity nitrogen), add a 10ml Schlek reaction tube (A glass instrument commonly used in anhydrous and oxygen-free operation) Add 1.0mmol p-bromoacetophenone, 1.3mmol 2-amino-5-bromobenzyl alcohol, 3.0mmol p-tolueneboronic acid, 0.01mmol RuCl 2 (DMSO) 4 , 0.03mmol palladium acetate, 0.1mmol triphenylphosphine, 5.0mmol 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 16 hours . 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 and filter; the filtrate is concentrated with a rotary evaporator, and the concen...

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PUM

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Abstract

The invention discloses 2-biaryl-6-arylquinazoline and a preparation method thereof, belonging to the field of organic synthesis. The technical scheme comprises that: the 2-biaryl-6-arylquinazoline has a general formula shown in the specification, wherein Aryl is an aryl group. The compound is prepared through the following steps: adding parabromoacetophenone, 2-amino-5-bromobenzenemethano, arylboronic acid, RuCl2(DMSO)4, palladium chloride, triphenylphosphine and alkaline into an organic solvent, carrying out heating reflux under the protection of inert gas, and after the reaction is ended, separating and purifying to obtain the 2-biaryl-6-arylquinazoline. The method can be used for synthesizing the 2-biaryl-6-arylquinazoline at one step and is mild in reaction condition, high in yield, economic and efficient in reaction and wide in application prospect.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a class of 2-biaryl-6-aryl quinoline compounds and a synthesis method of the compounds. Background technique [0002] Quinoline derivatives have biological activity and pharmacological activity, and are widely used in industrial production such as medicine and pesticide. 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. In recent years, on the basis of traditional synthetic routes, a new synthetic route using transition metal complexes as catalysts has been developed, which is currently the most studied and most promising method. In order to improve the atom economy and synthetic efficiency of the reaction, the one-pot multicomponent reaction to construct multiple covalent bonds has attracted widespread interest among chemi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/04C07D215/14C07D215/12C07F15/00
Inventor 李红梅徐晨王志强娄新华肖志强
Owner LUOYANG NORMAL UNIV