Method for electrochemical synthesis of indole compounds

A compound, electrochemical technology, applied in the field of electrochemical synthesis of indole compounds, can solve problems such as poor atom economy

Active Publication Date: 2021-04-27
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction yield is high, but equivalent iodobenzene or other by-pro...

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  • Method for electrochemical synthesis of indole compounds
  • Method for electrochemical synthesis of indole compounds
  • Method for electrochemical synthesis of indole compounds

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Embodiment 1

[0048] Put substrate (shown in formula 1-a) (0.3mmol, 82.0mg), potassium thiocyanate (0.3mmol, 29mg), tetramethylammonium iodide (0.3mmol, 60.3 mg), acetonitrile (5mL) and water (1mL), the platinum sheet electrode was used as both anode and cathode, and reacted under electric stirring (I=5mA) at 80°C. After the reaction was completed (TLC tracking detection), the residue obtained after rotary evaporation and concentration was passed through the chromatographic column with the ethyl acetate / petroleum ether system as the eluent to obtain the product N-Ts indole (shown in formula 1-b), the product The rate is 92%.

[0049] The indole product is analyzed by nuclear magnetic resonance spectrometer, the results can be found in Figure 1 ~ Figure 2 , figure 1 For the indole product that the embodiment of the present invention 1 provides 1 H NMR ( 1 H-NMR) spectrogram; figure 2 For the indole product that the embodiment of the present invention 1 provides 13 C NMR ( 13 C-NMR) ...

Embodiment 2

[0053] Put substrate (shown in formula 2-a) (0.3mmol, 89.5mg), potassium thiocyanate (0.3mmol, 29mg), tetramethylammonium iodide (0.3mmol, 60.3 mg), acetonitrile (5mL) and water (1mL), the platinum sheet electrode was used as both anode and cathode, and reacted under electric stirring (I=5mA) at 80°C. After the reaction was completed (TLC tracking detection), the residue obtained after rotary evaporation and concentration was used as an eluent through the chromatographic column to obtain the product 5-cyano N-Ts indole (formula 2-b) Shown), the productive rate is 66%.

[0054] The indole product is analyzed by nuclear magnetic resonance spectrometer, the results can be found in Figure 3 ~ Figure 4 , image 3 For the indole product that the embodiment of the present invention 2 provides 1 H NMR ( 1 H-NMR) spectrogram; Figure 4 For the indole product that the embodiment of the present invention 2 provides 13 C NMR ( 13 C-NMR) spectrogram.

[0055] Described product is ...

Embodiment 3

[0058] Put substrate (shown in formula 3-a) (0.3mmol, 94.6mg), potassium thiocyanate (0.3mmol, 29mg), tetramethylammonium iodide (0.3mmol, 60.3 mg), acetonitrile (5mL) and water (1mL), the platinum sheet electrode was used as both anode and cathode, and reacted under electric stirring (I=5mA) at 80°C. After the reaction was completed (TLC tracking detection), the residue obtained after rotary evaporation and concentration was passed through the chromatographic column with ethyl acetate / petroleum ether system as the eluent to obtain the product 5-acetyl N-Ts indole (formula 3-b) Shown), the productive rate is 74%.

[0059] The indole product is analyzed by nuclear magnetic resonance spectrometer, the results can be found in Figure 5 ~ Figure 6 , Figure 5 For the indole product that the embodiment of the present invention 3 provides 1 H NMR ( 1 H-NMR) spectrogram; Figure 6 For the indole product that the embodiment of the present invention 3 provides 13 C NMR ( 13 C-NM...

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Abstract

The invention provides a method for synthesizing an indole compound by iodine-induced electrocatalytic intramolecular C(sp2)-H oxidative cyclization. The preparation method comprises the following steps: mixing iodized salt electrolyte, a 2-vinyl aniline compound and thiocyanate, and performing an intramolecular oxidative cyclization reaction under electrochemical conditions to obtain the indole compound. The invention provides a method for non-metallic catalytic electrochemical synthesis of indole compounds, so that a plurality of important drug intermediates can be derived. According to the method, no metal or chemical oxidizing agent is used, no iodobenzene or other by-products are generated, the reaction is green and environmentally friendly, the atom economy is high, and the gram-scale experiment yield is kept.

Description

technical field [0001] The invention relates to the technical field of organic synthesis methodology, in particular to a method for electrochemically synthesizing indole compounds. Background technique [0002] Indole compounds widely exist in biologically active molecules and natural products, including alkaloids, polypeptides and various pharmaceutical intermediates. On the other hand, such derivatives are also commonly used raw materials in the preparation of functional materials, such as nonlinear optical materials, piezoelectric materials and photosensitive materials. Starting from Emil Fischer's pioneering synthesis, the synthesis of indole has received extensive attention for more than 130 years. [0003] In recent years, the research focus on the synthesis of indole compounds mainly focuses on transition metal catalysis. For example, the classic reaction: the oxidative cyclization of 2-vinylaniline to indole, which is an important symbol in the field of palladium c...

Claims

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Application Information

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IPC IPC(8): C25B3/23C25B3/09
Inventor 汪志勇胡康飞查正根
Owner UNIV OF SCI & TECH OF CHINA
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