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Method for synthesizing 3H-indol-3-one derivatives

A technology for derivatives and indole, which is applied in the field of synthesizing 3H-indole-3-one derivatives, can solve the problems of restricting the scope of application of synthetic methods, cumbersome reaction steps, and low overall yield, and reach the scope of application of substrates Wide range, simple operation, mild reaction conditions

Active Publication Date: 2018-08-21
HENAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods still have disadvantages such as cumbersome reaction steps, low overall yield, use of stoichiometric oxidants or expensive metal catalysts, and difficult availability of raw materials, which largely restrict the application range of this type of synthetic method.

Method used

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  • Method for synthesizing 3H-indol-3-one derivatives
  • Method for synthesizing 3H-indol-3-one derivatives
  • Method for synthesizing 3H-indol-3-one derivatives

Examples

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Embodiment 1

[0015]

[0016] In a 25mL reaction flask, add N-(2-(1H-indol-2-yl)phenyl)benzamide 1a (124.8mg, 0.4mmol), DMF (2mL) and CuBr (5.7mg, 0.04mmol) in sequence ), add dilute hydrochloric acid (0.16mL, 0.5M, 0.08mmol) under stirring at room temperature, and then heat and stir at 120°C for 4h. After the reaction is completed, add saturated sodium bicarbonate solution to the reaction bottle to quench the reaction, ethyl acetate After extraction, the organic phase was washed with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain red solid 3H-indol-3-one derivative 2a (91 mg, 70%). The characterization data of this compound are as follows: 1 H NMR (CDCl 3 ,400MHz)δ7.12(t,J=7.6Hz,1H),7.24(t,J=7.6Hz,2H),7.48-7.55(m,6H),8.07(d,J=8.0Hz,2H), 8.69(d, J=8.0Hz, 1H), 8.92(d, J=8.8Hz, 1H), 13.21(s, 1H); 13 C NMR (CDCl 3 ,100MHz)δ115.3,119.2,119.9,120.4,1...

Embodiment 2

[0018] According to the method described in Example 1, N-(2-(1H-indol-2-yl)phenyl)benzamide 1a (124.8mg, 0.4mmol), DMSO (2mL ) and CuI (7.6mg, 0.04mmol), add dilute hydrochloric acid (0.16mL, 0.5M, 0.08mmol) under stirring at room temperature, and then heat and stir at 120°C for 4h to prepare 3H-indol-3-one derivatives 2a (64 mg, 49%).

Embodiment 3

[0020] According to the method described in Example 1, N-(2-(1H-indol-2-yl)phenyl)benzamide 1a (124.8mg, 0.4mmol), DMSO (2mL ) and CuBr (5.7mg, 0.04mmol), add dilute hydrochloric acid (0.16mL, 0.5M, 0.08mmol) under stirring at room temperature, and then heat and stir at 120°C for 4h to prepare 3H-indol-3-one derivatives 2a (73 mg, 56%).

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Abstract

The invention discloses a method for synthesizing 3H-indol-3-one derivatives, and belongs to the technical field of organic synthesis. The key point of the technical scheme of the invention is as follows that the method for synthesizing the 3H-indol-3-one derivatives comprises the following specific steps: placing an N-(2-(1H-indole-2-yl)phenyl)benzamide compound, a solvent and a copper salt in areaction vessel, adding an acidic substance under stirring at room temperature, and carrying out a reaction at a temperature of 100-140 DEG C to obtain a target product 3H-indole-3-one derivative. Themethod provided by the invention has the advantages of mild reaction condition, simple operation and wide substrate application range.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing 3H-indol-3-one derivatives. Background technique [0002] 3H-indol-3-one derivatives not only widely exist in natural alkaloids, natural and synthetic dyes, but also exhibit important plasmodium killing activity, anti-malignant cell proliferation activity, antibacterial activity and CYP1A1 enzyme activity Inhibition activity has attracted more and more attention and research from organic and medicinal chemists in recent years. These compounds are usually prepared by a classic four-step synthesis, indole oxidation, and deoxygenation of indolinone nitrogen oxides. However, these methods still have disadvantages such as cumbersome reaction steps, low overall yield, use of stoichiometric oxidants or expensive metal catalysts, and difficult availability of raw materials, which largely restrict the application range of this type of synth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/36
CPCC07D209/36
Inventor 郭胜海孙林聪王芳陶丽范学森
Owner HENAN NORMAL UNIV
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