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Method for synthesizing quindoline derivative by visible light catalysis

A technology for indoloquinolines and indole derivatives is applied in the field of catalytic synthesis and achieves the effects of mild reaction conditions, simple operation and atomic economy

Active Publication Date: 2014-07-09
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Until now, there have been no patents or literature reports utilizing in situ generated metal complexes as both photosensitizers and catalysts to achieve cross-dehydrogenation coupling reactions

Method used

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  • Method for synthesizing quindoline derivative by visible light catalysis
  • Method for synthesizing quindoline derivative by visible light catalysis
  • Method for synthesizing quindoline derivative by visible light catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Add 0.1mmol 2-(4-methoxyanilino)methyl acetate and 0.02mmol copper trifluoromethanesulfonate to a 10mL reaction test tube, use 3mL dichloromethane as the reaction solvent, and add 0.2mmol1H-indole-1 under stirring -Tert-butyl carboxylate, after using LED (blue light) to illuminate the reaction solution for 10 h, the reaction solvent was spin-dried, and then separated by a column, and the yield of the obtained product was 10%. H NMR, C NMR, and mass spectrometry identified the product as tert-butyl 2-methoxy-6-methoxy-11H-indole[3,2-c]quinoline-11H-carboxylate.

[0042] figure 1 Be the general reaction formula of the present invention.

[0043] figure 2 UV-Vis absorption spectra of secondary amine 2-(4-methoxyanilino) ethyl acetate and copper trifluoromethanesulfonate at different concentrations in acetonitrile solvent. The secondary amine 2-(4-methoxyanilino)ethyl acetate has no absorption in the visible light region (as shown in the figure, the concentration of the...

Embodiment 2

[0046] Same as Example 1, the difference is that LED (blue light) is used to illuminate the reaction solution for 20 hours, and the yield of the product obtained is 25%.

Embodiment 3

[0048] Same as Example 1, the difference is that after the reaction solution is illuminated by LED (blue light) for 30 hours, the yield of the product obtained is 28%.

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Abstract

The invention discloses a method for synthesizing a quindoline derivative by visible light catalysis. The method uses metal salt to synthesize the quindoline derivative through photocatalysis. According to the invention, extra photosensitizer is not required, cheap transition metal salt and secondary amine enable in-situ coordination to generate a compound which is taken as a photocatalyst, oxygen in air is taken as a terminal oxidizing agent, so that oxidation coupling of secondary amine and an indole derivative can be realized through a photochemical method, and the quindoline derivative enables one-step synthesis. The whole synthesis reaction has the advantages of mild condition, high efficiency, simple operation and atom economy.

Description

technical field [0001] The invention belongs to the field of catalytic synthesis, and relates to the synthesis of indoloquinoline derivatives, in particular to a method for catalytically synthesizing indoloquinoline derivatives by using visible light. Background technique [0002] Today's material civilization is unprecedentedly developed, and chemistry, which is closely connected with matter, has contributed a lot. In the fields of energy, materials, medicine, food, etc., all of them demonstrate the great achievements of chemistry. But at the same time, the discharge of "three wastes" in the production of chemical industry has aggravated the pollution of the environment. In order to improve the efficiency of energy utilization and minimize environmental pollution, scientists propose to develop energy-economical reactions, that is, chemical reactions must meet the requirements of green chemistry. Green chemistry, also known as environment-friendly chemistry, one of its cor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 吴骊珠孟庆元雷涛高学旺钟建基向明陈彬佟振合
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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