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A kind of synthetic method of indazolo[2,3-a]quinoline and derivatives thereof

A derivative, 3-a technology, applied in the direction of chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve the problems of complex operation, large substrate limitations, long reaction route, etc., achieve high atom economy, catalytic Efficient system and easy operation

Active Publication Date: 2021-03-02
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the existing synthetic methods basically have one or more of the following disadvantages: such as expensive or rare starting materials, long reaction routes, complicated operations, large substrate limitations, poor atom economy, and poor overall yields. Disadvantages such as low

Method used

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  • A kind of synthetic method of indazolo[2,3-a]quinoline and derivatives thereof
  • A kind of synthetic method of indazolo[2,3-a]quinoline and derivatives thereof
  • A kind of synthetic method of indazolo[2,3-a]quinoline and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Add silver hexafluoroantimonate (0.1mmol) and sodium carbonate (0.2mmol) in a closed pressure-resistant tube, add dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer (0.05mmol) , then added 2-styrylaniline (0.1 mmol), added dropwise 2 mL of xylene to dissolve it, and then added azidobenzaldehyde (0.2 mmol); followed the reaction by TLC in an oil bath at 110° C. for 12 h. After the reaction, the reaction system was filtered, extracted three times with ethyl acetate, and the organic phases were combined and dried with anhydrous sodium sulfate. Filter, evaporate the solvent as much as possible, adsorb on silica gel, and separate by column chromatography to obtain the target product. Column chromatography EA:PE=1:30, the target product was isolated. Yield 72%; m.p.: 151-153°C. The excitation wavelength is 379nm, the fluorescence emission wavelength is 440nm, the solvent is ethyl acetate, and the temperature is 298K.

[0043] 1 H NMR (400MHz, CDCl 3 )δ9.06(d, J=...

Embodiment 2

[0046] Add copper acetate (0.1mmol) and sodium carbonate (0.2 mmol) to the airtight pressure-resistant tube under oxygen atmosphere, add dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer (0.05mmol ), then added 2-styrylaniline (0.1 mmol), added dropwise 2 mL of chlorobenzene to dissolve it, and then added azidobenzaldehyde (0.1 mmol); followed the reaction by TLC at 100° C. in an oil bath for 12 h. After the reaction, the reaction system was filtered, extracted three times with ethyl acetate, and the organic phases were combined and dried with anhydrous sodium sulfate. Filter, evaporate the solvent as much as possible, adsorb on silica gel, and separate by column chromatography to obtain the target product. Column chromatography EA:PE=1:30, the target product was isolated. Yield 64%.

Embodiment 3

[0048] Add silver hexafluoroantimonate (0.1mmol) and sodium carbonate (0.3mmol) in a closed pressure-resistant tube, add dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer (0.02mmol) , then added 2-styrylaniline (0.1 mmol), added dropwise 2 mL of toluene to dissolve it, and then added azidobenzaldehyde (0.3 mmol); followed the reaction by TLC in an oil bath at 140° C. for 12 h. After the reaction, the reaction system was filtered, extracted three times with ethyl acetate, and the organic phases were combined and dried with anhydrous sodium sulfate. Filter, evaporate the solvent as much as possible, adsorb on silica gel, and separate by column chromatography to obtain the target product. Column chromatography EA:PE=1:30, the target product was isolated. Yield 60%.

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Abstract

The invention belongs to the field of organic chemical medicine, and particularly relates to a synthesis method of imidazo[2,3-a]quinoline and a derivative thereof. According to the method, 2-aromaticvinyl aniline or a derivative thereof and o-azaraldehyde serve as raw materials, a catalyst and an additive are added, then a proper quantity of a solvent is added, a stirring reaction is carried outfor 5-24 h at 50-150 DEG C with air or oxygen as an oxidizing agent, after the reaction is finished, the reaction system is extracted by ethyl acetate 3 times, organic phases are merged, and anhydrous sodium sulfate is utilized for drying; filtering is conducted, the solvent is evaporated away as many as possible, and chromatographic separation or recrystallization is conducted through a silicagel column to obtain a target product; 2-aromatic vinyl aniline and o-azaraldehyde directly serve as the raw materials and are subjected to a one-pot reaction for synthesizing imidazo[2,3-a]quinoline and the derivative thereof with visible fluorescence activities.

Description

technical field [0001] The invention belongs to the field of organic chemical industry and medicine, in particular to a method for synthesizing indazolo[2,3-a]quinoline and its derivatives by using 2-arylvinylaniline or its derivatives and o-azide aromatic aldehyde as raw materials . These compounds all have visible light fluorescence activity. Background technique [0002] Indazolo[2,3-a]quinoline and its derivatives have unique biological activities. If it has good antitumor activity (Khan, I., Ibrar, A., Ahmed, W., et al. Eur J Med Chem, 2015, 90, 124.), it can also be used as a pesticide (McCann, S.F., Annis , G.D., Shapiro, R., et al. Pest Manag Sci, 2001, 57, 153.). In addition, it has been used in organic dyes (Luo, C., Zhou, Q., Jiang, G., et al. New J Chem, 2011, 35, 1128.), luminescent materials (Wragg, D.A., Watson, T.M., ECS Transactions ,2013,53,19.) and other fields also have potential application value. However, due to the great synthetic challenge of its...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07D491/147C09K11/06
CPCC07D471/04C07D491/147C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1088
Inventor 邵莺潘乐昊黄磊胡卫明崔晓彤吴铭
Owner CHANGZHOU UNIV