Method for synthesizing multi-substituted quinoline compound

A quinoline-based, multi-substitution technology, applied in the field of synthesis of drug molecules and their analogs, can solve the problems of heavy metal drug residues, unsuitable for wide application, and difficult separation and recovery of transition metal catalysts, achieving easy separation and low dosage Effect

Inactive Publication Date: 2013-07-24
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation of quinoline by the Baylis-Hillman synthesis method is widely used in organic synthesis, mainly due to the strict requirements on the substrate, and the separation and purification of products is very inconvenient, so it is only suitable for the preparation of quinoline derivatives with special structures
In recent years, it has been reported that transition metals can be used as acid catalysts to synthesize quin

Method used

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  • Method for synthesizing multi-substituted quinoline compound
  • Method for synthesizing multi-substituted quinoline compound
  • Method for synthesizing multi-substituted quinoline compound

Examples

Experimental program
Comparison scheme
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Embodiment Construction

[0019] One, take synthetic 2,3-diphenylquinoline-3-carboxylic acid ethyl ester as example production steps:

[0020] 1. Add 1g of raw material 3-(1,2-diphenylethanon-2-yl)indol-2-one, 50mL of absolute ethanol, 50mL of chloroform and 0.01g of p-toluenesulfonic acid into a 250mL round bottom flask .

[0021] 2. The above mixture was heated to 70°C, stirred and kept for 30 minutes.

[0022] 3. Pour the solution obtained after the reaction in step 2 into 150 mL of water to precipitate solids.

[0023] 4. The above solid was filtered out without further purification to obtain the final compound—ethyl 2,3-diphenylquinoline-3-carboxylate.

[0024] 5. Reaction formula:

[0025]

[0026] 2. Verification:

[0027] Adopt the structural diagram of the product that the inventive method obtains, as figure 1 as shown in figure 2 The spectra shown are verified as follows:

[0028]

[0029] 5,8-Dichloro-2,3-diphenylquinoline-4-carboxylic acid ethyl ester

[0030] White solid, ...

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Abstract

The invention provides a method for synthesizing a multi-substituted quinoline compound and relates to a method for synthesizing a drug molecule containing a quinoline structure and an analogue thereof. Sertindole-2-atone containing a 1,4-dicarbonyl structure, absolute ethanol, chloroform and p-toluenesulfonic acid are added into a container, heating and reacting are carried out, and solids in mixture of reaction liquid and water are extracted and filtered after reaction is finished, namely the synthesized multi-substituted quinoline compound is obtained. According to the method provided by the invention, absolute ethanol and chloroform are taken as a mixed solvent, and the defect that a single solvent is poor in solubility is overcome; p-toluenesulfonic acid serves as a catalyst and is easy to separate, low in dosage and environment-friendly; and post treatment is extremely easy, and only the solids need to be extracted and filtered.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of a class of drug molecules containing quinoline structures and analogs thereof. Background technique [0002] The quinoline ring structure widely exists in natural products and synthetic drugs, and this type of compound is one of the most important drug classes in the history of antimalarials. In recent years, with the in-depth research on heterocyclic drugs, especially the research on the synthesis of various substituted quinoline molecules and their physiological activities, the application of substituted quinolines in medicine has attracted more and more attention. . Such molecules have good prospects for drug development. [0003] The existing quinolines are prepared by extraction from coal tar or synthesis by catalytic chemical methods. Due to the low content and single species in coal tar, only a small amount of quinoline compounds with a ...

Claims

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Application Information

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IPC IPC(8): C07D215/52C07D405/04
Inventor 景崤壁冯浩潘生玉孙舒雅
Owner YANGZHOU UNIV
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