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Method for preparing 2-aryl-4-methyl quinoline compound

A technology of methylquinoline and compounds, which is applied in the field of preparation of 2-aryl-4-methylquinoline compounds, can solve problems such as the inability to synthesize 2-aryl-4-methylquinoline compounds, and achieve Low cost, easy post-processing, and strong designability

Inactive Publication Date: 2016-08-03
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since this method is a ring-closure reaction of propargyl allene rearrangement initiated by the nitrogen atom in the amide alkynylimine in the presence of DBU, it is limited by the substrate, so it is impossible to synthesize 2-aryl-4-methanone Quinolines

Method used

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  • Method for preparing 2-aryl-4-methyl quinoline compound
  • Method for preparing 2-aryl-4-methyl quinoline compound
  • Method for preparing 2-aryl-4-methyl quinoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Add 2.0 mmol of potassium fluoride, 1.0 mmol of alkynyl imine compound (as shown in formula I-1) and an appropriate amount of dichloromethane into a 25 ml Schlenk tube, mix and stir evenly, and react at 50°C 8h, post-processing (quenching the reaction with water, collecting the organic layer by extraction, mixing the sample with silica gel, evaporating the organic solvent to dryness, and purifying by column chromatography (petroleum ether:ethyl acetate=10:1)) to obtain the corresponding 2-aryl-4-methylquinoline compound (as shown in formula II-1), the yield of the product is 73%.

[0028]

Embodiment 2

[0029] Example 2: In a 25ml Schlenk tube, add 2.0mmol of potassium fluoride, 1.0mmol of an alkynyl imine compound (as shown in formula I-2) and an appropriate amount of 1,2-dichloroethane, mix and stir evenly , react at 60°C for 8h, post-treatment (quench the reaction with water, collect the organic layer by extraction, mix the sample with silica gel, evaporate the organic solvent to dryness, and perform column chromatography (eluent is petroleum ether: ethyl acetate=10:1) purification) to obtain the corresponding 2-aryl-4-methylquinoline compound (as shown in formula II-2), and the yield of the product is 77%.

[0030]

Embodiment 3

[0031] Example 3: Add 2.2mmol of potassium fluoride, 1.0mmol of alkynyl imine compound (as shown in formula I-3) and an appropriate amount of N,N-dimethylformamide in a 25ml Schlenk tube, mix and stir Uniform, react at 70°C for 10 h, post-treatment (quench the reaction with water, collect the organic layer by extraction, mix the sample with silica gel, evaporate the organic solvent to dryness, and perform column chromatography (eluent is petroleum ether: ethyl acetate=10:1 ) purification) to obtain the corresponding 2-aryl-4-methylquinoline compound (as shown in formula II-3), and the yield of the product is 85%.

[0032]

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Abstract

The invention discloses a method for preparing a 2-aryl-4-methyl quinoline compound. The method comprises the following steps of: adding fluoride and an alkynyl imine compound into an organic solvent, and heating to react completely, wherein the structural formula of the alkynyl imine compound is as shown in the specification, and the structural formula of the 2-aryl-4-methyl quinoline compound is a shown in the specification, in the formulas, R1 is hydrogen, halogen, methyl, methoxyl, thiophene or cyanogen radical; R2 is hydrogen, methyl or methoxyl. Compared with the prior art, the 2-aryl-4-methyl quinoline compound can be prepared from one organism of the alkynyl imine compound under the action of the fluoride at one stime. The method disclosed by the invention is easy to operate and simple and convenient in aftertreatmnet, and the designability of substrates is good.

Description

technical field [0001] The invention relates to a preparation method of a 2-aryl-4-methylquinoline compound, belonging to the field of organic synthesis. Background technique [0002] Quinoline is an important heterocyclic compound, which is widely used in the fields of medicine, dyes, fungicides and corrosives. Quinoline derivatives are the skeleton structures of various natural products, which have anti-tumor, anti-bacterial, anti-inflammatory and anti-hypertensive effects. A large number of studies show that quinolines can be used in medicines (document I: Pharmacomodulations around the 4-oxo-1, 4-dihydroquinoline-3-carboxamides, a class of potent CB2-selective cannabinoid receptor ligands: consequences in receptor affinity and functionality. ). Document II: Pyrrolo (iso) quinoline derivatives as 5-HT (2C) receptoragonists. Adams David R, Bentley Jonathan M, Benwell Karen R. Bioorganic & Medicinal Chemistry Letters, 2006, 16 (3).). Quinoline compounds also have broad ap...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/06C07D215/12C07D215/20C07D409/04
CPCC07D215/06C07D215/12C07D215/20C07D409/04
Inventor 单营营阎卫东
Owner ZHEJIANG UNIV