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Electrochemical preparation method for 3-selenium aryl indole compounds

A technology of selenium aryl indole and compound, which is applied in the field of electrochemical organic synthesis, can solve the problems of adding alkali, heating, and low tolerance of functional groups, and achieve the effects of good reaction selectivity, simple operation, and simple and efficient reaction system

Inactive Publication Date: 2017-03-29
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above methods have good yields, there are still disadvantages such as the need for heating, low tolerance of functional groups, and the need to add alkali.

Method used

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  • Electrochemical preparation method for 3-selenium aryl indole compounds
  • Electrochemical preparation method for 3-selenium aryl indole compounds
  • Electrochemical preparation method for 3-selenium aryl indole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] With metal platinum as the anode and nickel mesh as the cathode, add 1mmol LiClO in turn to the round bottom flask 4 , 0.02mmolNaI, 0.2mmol indole, 0.11mmol diphenyldiselenide, 5mL MeOH, 85μL H 2 O. Magnetic stirrer, cover the lid, turn on the power supply, adjust the current to 3mA, and electrolyze for 10h at room temperature. After the reaction, the crude product was extracted with ethyl acetate, and the corresponding product 3a was obtained after separation and purification, and the yield of the product 3a was 92%. The reaction scheme of the present embodiment is as follows:

[0036]

[0037] The proton nuclear magnetic resonance spectrum of the product of this embodiment is as follows: figure 1 shown in [ 1 H NMR (400MHz, CDCl 3 ): δ(ppm)8.38(brs,1H),7.62(d,J=7.9Hz,1H),7.41-7.38(m,2H),7.26-7.21(m,3H),7.17-7.07(m,4H )]; C NMR spectrum such as figure 2 shown in [ 13 C NMR (100MHz, CDCl 3): δ (ppm) 136.4, 133.8, 131.2, 129.9, 128.9, 128.7, 125.6, 122.9, 120...

Embodiment 2

[0040] With the mesh glassy carbon electrode (RVC electrode) as the anode and the nickel mesh as the cathode, add 1 mmol NH in turn to the round bottom flask 4 BF 4 , 0.4mmol NaI, 0.2mmol indole, 0.4mmol diphenyl diselenide, 5mL MeOH, 85μL H 2 O. Magnetic stirrer, cover the lid, turn on the power supply, adjust the current to 3mA, and electrolyze for 10h at room temperature. After the reaction, the crude product was extracted with ethyl acetate, and the corresponding product 3a was obtained after separation and purification, and the yield of the product 3a was 96%.

Embodiment 3

[0042] With the mesh glassy carbon electrode (RVC electrode) as the anode and metal platinum as the cathode, 1 mmol Bu was added to the round bottom flask successively. 4 NClO 4 , 0.2mmol NaI, 0.2mmol indole, 0.25mmol diphenyldiselenide, 5mL MeOH, 85μL H 2 O. Magnetic stirrer, cover the lid, turn on the power supply, adjust the current to 3mA, and electrolyze for 10h at room temperature. After the reaction, the crude product was extracted with ethyl acetate, and the corresponding product 3a was obtained after separation and purification, and the yield of the product 3a was 93%.

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Abstract

The innveiton discloses an electrochemical preparation method for 3-selenium aryl indole compounds, and belongs to the technical field of electrochemical organic synthesis. The preparation method comprises the following steps of: sequentially adding electrolyte, sodium iodide, indole compounds, diselenium aromatic ether compounds and an electrolytic solvent into an electrolytic tank without a diaphragm; inserting an anode and a cathode; stirring and electrifying, reacting under a constant-current condition; and after reaction is completed, carrying out organic extraction on an electrolyte solution by use of an organic solvent, and separating and extracting to obtain the 3-selenium aryl indole compounds. According to the electrochemical preparation method disclosed by the invention, an anode electrode is used as a platinum electrode or a net-shaped glass-state carbon electrode (RVC electrode), the cathode is a nickel net or a net-shaped glass-state carbon electrode (RVC electrode) or platinum, the yield is high, selectivity is good, and a metal catalyst does not need to be additionally added, so that a catalyst which is poisonous, dear and complex to prepare is effectively prevented from being used, a reaction system is simple and effective, and the electrochemical preparation method is environmentally friendly. The method disclosed by invention is operated under normal pressure at a normal temperature, and is simple and safe.

Description

technical field [0001] The invention belongs to the technical field of electrochemical organic synthesis, and relates to a synthesis method of 3-selenoarylindole compounds, in particular to an electrochemical preparation method of 3-selenoarylindole compounds. Background technique [0002] 3-selenoarylindole compounds are an important class of heterocyclic organic selenium compounds. Because of their remarkable biological activity, some compounds containing 3-selenoarylindole structural units have been used to treat allergies, tumors, Heart disease, AIDS, obesity and other diseases. In addition, the 3-selenoarylindole skeleton plays an important role in organic synthesis. [0003] There are two main synthetic strategies for 3-selenoarylindoles. One is to use transition metal catalysis to synthesize 3-selenoarylindole compounds through the electrophilic cyclization reaction of o-alkynyl aniline compounds and electrophilic selenium reagents. 2011 Jin-Heng Li and Xing-Guo Zh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/00
CPCC25B3/00
Inventor 黄精美林殿朝
Owner SOUTH CHINA UNIV OF TECH
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