Electrochemical synthesis method of 1,1'-diindolylmethane derivatives

A technology of diindolylmethane and indole derivatives, applied in electrolysis process, electrolysis components, electrolysis organic production and other directions, can solve the problem of high cost and achieve the effects of low cost, wide application range and mild conditions

Inactive Publication Date: 2017-04-19
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

From the point of view of reaction conditions, when Lewis acid catalysis or protonic acid catalysis is used, in most cases, equivalent or excess is required, and in some cases even heating or reflux is required; when metal catalysis is used, it is somet...

Method used

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  • Electrochemical synthesis method of 1,1'-diindolylmethane derivatives
  • Electrochemical synthesis method of 1,1'-diindolylmethane derivatives
  • Electrochemical synthesis method of 1,1'-diindolylmethane derivatives

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Experimental program
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Effect test

Embodiment 1

[0045] Add 19.5mg (0.08mmol) LaCl to a 5ml round-bottomed flask 3 ,106.4mg(0.2mmol / ml)LiCIO 4 , 104.9 mg (0.8 mmol) N-methyl indole; then 3.3 ml of tetrahydrofuran and 1.7 ml of acetonitrile were added. Insert two electrodes (the platinum wire is the anode and the platinum sheet is the cathode), the DC power supply is powered at 5mA, the reaction is stirred and monitored by TLC, and the reaction is complete in 4.5h. The crude product was extracted with ethyl acetate (15ml×3), the organic layers were combined, washed with saturated aqueous NaCI solution (40ml×1), and anhydrous Na 2 SO 4 After drying, evaporated to dryness under reduced pressure, the product 1 was isolated in a yield of 82.4%.

[0046]

Embodiment 2

[0048] Add 19.5mg (0.08mmol) LaCl to a 5ml round-bottomed flask 3 , 106.4mg (the concentration in the electrolytic solvent is 0.2mmol / ml) LiCIO 4 , 104.9 mg (0.8 mmol) N-methyl indole; then 3.3 ml of tetrahydrofuran and 1.7 ml of acetonitrile were added. Insert two electrodes (the platinum wire is the anode and the platinum sheet is the cathode), the DC power supply is powered at 2.5mA or 8mA, the reaction is stirred and monitored by TLC, and the reaction is complete in 4.5h. The crude product was extracted with ethyl acetate (15ml×3), the organic layers were combined, washed with saturated aqueous NaCI solution (40ml×1), and anhydrous Na 2 SO 4 Dry, evaporate to dryness under reduced pressure, and isolate the product 1 in a yield of 32.8% (2.5mA) or 45.7% (8mA).

[0049]

Embodiment 3

[0051] Add 19.5mg (0.08mmol) LaCl to a 5ml round-bottomed flask 3 , 106.4mg (the concentration in the electrolytic solvent is 0.2mmol / ml) LiCIO 4 , 104.9 mg (0.8 mmol) of N-methyl indole; then 5 ml of a mixed solvent of tetrahydrofuran / acetonitrile (v / v) (1:1 or 3:1) was added. Insert two electrodes (the platinum wire is the anode and the platinum sheet is the cathode), the DC power supply is powered at 5mA, the reaction is stirred and monitored by TLC, and the reaction is complete in 4.5h. The crude product was extracted with ethyl acetate (15ml×3), the organic layers were combined, washed with saturated aqueous NaCI solution (40ml×1), and anhydrous Na 2 SO 4 Dry and evaporate to dryness under reduced pressure to obtain product 1 in a yield of 47.5% (1:1) or 62.3% (3:1).

[0052]

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Abstract

The invention discloses an electrochemical synthesis method of 1,1'-diindolylmethane derivatives. According to the method, indole derivatives, tetrahydrofuran and tetrahydrofuran derivatives are used as raw materials for synthetizing the 1,1'-diindolylmethane derivatives under the electrochemical condition. The method specifically comprises the following steps that the indole derivatives are taken and added into a mixed solvent of the tetrahydrofuran or tetrahydrofuran derivatives with acetonitrile, and a catalytic amount of lanthanum chloride and electrolyte lithium perchlorate are added; a platinum electrode is inserted into reaction liquid, stirring is conducted at the room temperature, and a reaction is carried out through electrification until the complete reaction is conducted; and the reaction liquid is extracted, concentrated and separated, and the 1,1'-diindolylmethane derivatives is obtained. Electricity is used for catalysis, expensive metal catalyzers and other oxidizing agents are not needed, stoichiometric lewis acid, protonic acid and heating are not needed either, reaction can be carried out mildly at the room temperature, the selectivity is good, the yield is high, and the whole process is simple and feasible; and the method is environmentally friendly and conforms to the idea of green chemistry.

Description

technical field [0001] The invention belongs to the field of organic electrosynthesis chemistry, relates to a method for synthesizing 1,1'-diindolylmethane derivatives, and in particular relates to a method for synthesizing 1,1'-diindolylmethane derivatives by using N-substituted indole and derivatives, tetrahydrofuran and tetrahydrofuran derivatives as raw materials, Methods of 1'-diindolylmethane derivatives. Background technique [0002] Many biologically active natural products contain indole derivatives, especially 1,1'-diindolylmethanes isolated from some terrestrial and marine organisms in recent years have shown better biological activity, Such as coronary dilating properties, genotoxicity, antibacterial activity and anticancer activity. Therefore, it has aroused the interest of many organic chemists and conducted extensive research on synthetic methods. [0003] At present, the main synthetic method is the condensation of aldehydes or ketones with indole or indole...

Claims

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Application Information

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IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 黄精美杜克斯
Owner SOUTH CHINA UNIV OF TECH
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