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Preparation method of spiro indolone compound in water phase

A technology of spiro indolinone and compound, which is applied in the field of catalytic synthesis of fine chemical industry, can solve the problems such as the limitation of yield and substrate universality, and achieve the effects of easy reaction scale, short process flow and high yield

Active Publication Date: 2019-05-21
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are only a few reports on the synthesis of spiro indolinone derivatives through iodonium salt-catalyzed intramolecular reactions, and these reactions need to be carried out in organic solvents. In terms of the yield of the reaction and the universality of the substrate are also limited

Method used

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  • Preparation method of spiro indolone compound in water phase
  • Preparation method of spiro indolone compound in water phase
  • Preparation method of spiro indolone compound in water phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063]

[0064] Add substrate (0.2mmol, 50.6mg), trimethyldodecyl ammonium iodide (0.02mmol, 7.2mg), 2ml of water, and finally hydrogen peroxide (0.6mmol, 60 μL). The reaction mixture was stirred at room temperature for 24 h, and the reaction was stopped. Ethyl acetate (5 mL*4) was added to the reaction system for extraction. The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to obtain a crude product. The obtained crude product was purified and separated by column chromatography to obtain a white solid product with an isolated yield of 98%. figure 1 It is the proton nuclear magnetic resonance spectrum of the target product obtained in Example 1.

[0065] 1 H NMR (600MHz, CDCl 3 )δ7.36(td, J=7.8,1.0Hz,1H),7.29(d,J=7.3Hz,1H),7.25(d,J=7.5Hz,1H),7.19(t,J=7.7Hz, 1H), 7.06(t, J=7.5Hz, 1H), 6.95(t, J=7.4Hz, 1H), 6.88(d, J=4.3Hz, 1H), 6.86(d, J=4.2Hz, 1H) , 3.73 (d, J = 15.8Hz, 1H), 3.45 (d, J = 15.8Hz, 1H), 3.23 (s, 3H)....

Embodiment 2

[0067]

[0068] Add substrate (0.2mmol, 53.4mg), trimethyldodecyl ammonium iodide (0.02mmol, 7.2mg), 2ml of water, and finally hydrogen peroxide (0.6mmol, 60 μL). The reaction mixture was stirred at room temperature for 24 h, and the reaction was stopped. Ethyl acetate (5 mL*4) was added to the reaction system for extraction. The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to obtain a crude product. The obtained crude product was purified and separated by column chromatography to obtain a white solid product with an isolated yield of 88%. figure 2 It is the proton nuclear magnetic resonance spectrum of the target product obtained in Example 2.

[0069] 1 H NMR (600MHz, CDCl 3 )δ7.24(d, J=7.2Hz, 1H), 7.18(t, J=7.6Hz, 1H), 7.13(d, J=7.3Hz, 1H), 7.09(d, J=7.7Hz, 1H) ,6.96–6.91(m,2H),6.86(d,J=8.0Hz,1H),3.71(d,J=15.8Hz,1H),3.51(s,3H),3.41(d,J=15.8Hz, 1H), 2.58(s, 3H).

Embodiment 3

[0071]

[0072] Add substrate (0.2mmol, 47.8mg), trimethyldodecyl ammonium iodide (0.02mmol, 7.2mg), 2ml of water, and finally hydrogen peroxide (0.6mmol, 60 μL). The reaction mixture was stirred at room temperature for 24 h, and the reaction was stopped. Ethyl acetate (5 mL*4) was added to the reaction system for extraction. The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to obtain a crude product. The obtained crude product was purified and separated by column chromatography to obtain a white solid product with an isolated yield of 87%. image 3 It is the proton nuclear magnetic resonance spectrum of the target product obtained in Example 3.

[0073] 1 H NMR (600MHz, CDCl 3 )δ8.64(s,1H),7.30–7.24(m,3H),7.20(t,J=7.6Hz,1H),7.03(t,J=7.5Hz,1H),6.96(t,J=7.4 Hz, 1H), 6.89 (dd, J=8.0, 2.2Hz, 2H), 3.75 (d, J=15.9Hz, 1H), 3.48 (d, J=15.9Hz, 1H).

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Abstract

The invention belongs to the technical field of fine chemical catalysis synthesis, and more specifically relates to a preparation method of a spiro indolone compound in a water phase. According to themethod, an indolone-derived compound containing active hydrogen functional groups or a 3-indole propionic acid derivative is used as a raw material, a quaternary ammonium iodide salt is used as a catalyst and a surfactant, a peroxide is used as an oxidizing agent, and reacting is performed in the water phase to obtain the spiro indolone compound. According to the method provided by the invention,any organic solvent can be completely avoided during reaction, and the method is green and environment-friendly, high in yield, mild in condition, simple and convenient to operate, good in reaction medium cycle performance and the like.

Description

technical field [0001] The invention belongs to the technical field of catalytic synthesis of fine chemical industry, and more specifically relates to a preparation method of spiro indolinone compounds in water phase. Background technique [0002] Spiroindolinone derivatives widely exist in many natural products and drug molecules, which have rich drug and biological activities, such as anti-tuberculosis, anti-cancer, anti-HIV, anti-malarial and other activities. Therefore, synthetic chemists and pharmacologists have been actively investigating new methods for the efficient synthesis of these compounds. [0003] Oxidation reactions are one of the basic reaction types in organic synthesis. In recent years, the catalytic oxidation system combined with iodine salt / peroxide has become a common and effective means in oxidative coupling reactions. At present, there are only a few reports on the synthesis of spiro indolinone derivatives through iodonium salt-catalyzed intramolecu...

Claims

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Application Information

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IPC IPC(8): C07D209/18C07D491/107C07D487/10
Inventor 钟芳锐王丹桂
Owner HUAZHONG UNIV OF SCI & TECH
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