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Polysubstituted thienoindole derivative and preparation method thereof

A technology of indole derivatives and multiple substitutions, applied in organic chemistry and other fields, can solve the problems of large environmental pollution, expensive catalytic metals, and high toxicity of reagents, and achieve the effects of scientific and reasonable synthesis methods, simple synthesis methods, and easy-to-use products

Inactive Publication Date: 2016-08-03
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Utilize above-mentioned method to prepare thienoindole derivatives in the laboratory, have obvious shortcoming: 1) synthetic steps are many, loaded down with trivial details operation, catalytic metal is expensive
2) The reaction is carried out under strong acid or strong alkaline conditions, causing great environmental pollution; 3) Some reagents are highly toxic and the reaction conditions are harsh

Method used

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  • Polysubstituted thienoindole derivative and preparation method thereof
  • Polysubstituted thienoindole derivative and preparation method thereof
  • Polysubstituted thienoindole derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: (Z)-N-cyclohexyl-3-phenyl-2H-thieno[2,3-b]indol-2-amine (R in structural formula I 1 = cyclohexyl, R 2 = phenyl, R 3 = Hydrogen atom, R 4 = Hydrogen atom)

[0025] Add 2-phenylethynyl-phenylisothiocyanate (1.0mmol, 235mg), cyclohexylisonitrile (1.2mmol, 153uL) and nickel acetylacetonate (0.003mmol, 0.88mg) to a 25mL round bottom flask, add 3.0 mL of redistilled tetrahydrofuran, sealed and placed in an oil bath at 80°C for 5 hours. After the reaction was complete, cool to room temperature, extract the system with ethyl acetate, then evaporate the solvent with a rotary evaporator, and separate the residue by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=20 / 1) The red solid product (Z)-N-cyclohexyl-3-phenyl-2H-thieno[2,3-b]indol-2-amine 336 mg with a purity greater than 99% was obtained. The isolated yield was 96%.

[0026] Structural identification of (Z)-N-cyclohexyl-3-phenyl-2H-thieno[2,3-b]indol-2-amine:

[0027] 1 HNM...

Embodiment 2

[0028] Example 2: (Z)-N-cyclohexyl-3-(4-fluorophenyl)-2H-thieno[2,3-b]indole-2-imine (R in structural formula I 1 = cyclohexyl, R 2 = p-fluorophenyl, R 3 = Hydrogen atom, R 4 = Hydrogen atom)

[0029] To a 25 mL round bottom flask was added (3-fluorophenyl)ethynyl-phenylisothiocyanate (1.0 mmol, 253 mg), cyclohexylisonitrile (1.2 mmol, 153 uL) and nickel acetylacetonate (0.003 mmol, 0.88 mg ), add 3.0 mL redistilled tetrahydrofuran, seal the mouth and put it in an oil bath at 80°C for 5 hours. After the reaction was complete, cool to room temperature, extract the system with ethyl acetate, then evaporate the solvent with a rotary evaporator, and separate the residue by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=20 / 1) The product (Z)-N-cyclohexyl-3-(4-fluorophenyl)-2H-thieno[2,3-b]indole-2-imine was obtained as a red solid with a purity greater than 99% 294 mg isolated yield 95%.

[0030] Structural identification of (Z)-N-cyclohexyl-3-...

Embodiment 3

[0032] Example 3: (Z)-N-cyclohexyl-5-fluoro-3-phenyl-2H-thieno[2,3-b]indol-2-amine (R in structural formula I 1 = cyclohexyl, R 2 = phenyl, R 3 = fluorine atom, R4 = Hydrogen atom)

[0033] Into a 25 mL round bottom flask was added 4-fluoro-2-(phenylethynyl)-phenylisothiocyanate (1.0 mmol, 253 mg), cyclohexylisonitrile (1.2 mmol, 153 uL) and nickel acetylacetonate (0.003 mmol ,0.88mg), add 3.0mL redistilled tetrahydrofuran, seal the mouth and put it in an oil bath at 80°C for 5h. After the reaction was complete, cool to room temperature, extract the system with ethyl acetate, then evaporate the solvent with a rotary evaporator, and separate the residue by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=20 / 1) The product (Z)-N-cyclohexyl-5-fluoro-3-phenyl-2H-thieno[2,3-b]indol-2-amine 330mg with a purity of more than 99% was obtained. The isolated yield was 93% .

[0034] Structural identification of (Z)-N-cyclohexyl-5-fluoro-3-phenyl-2H-thie...

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PUM

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Abstract

The invention discloses a method for preparing a polysubstituted thienoindole derivative, and the method belongs to the technical field of organic synthesis. The method comprises the following steps: adding ortho-alkynyl isothiocyanate and isonitrile into a reactor; under the catalysis of nickel, heating an obtained mixture in a solvent, cooling an obtained reaction product to a room temperature after completing the reaction, extracting a system by ethyl acetate, then concentrating a filtrate by a rotary evaporator to obtain a crude product, and finally separating the crude product by a column chromatography to obtain a product. The method for preparing the polysubstituted thienoindole derivative, which is provided by the invention, is scientific and reasonable, the productivity is relatively high and the product is purified easily.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of multi-substituted 2H-thieno[2,3-b]indole derivatives. Background technique [0002] Thienoindole derivatives are a common class of heterocyclic compounds with biological and pharmacological activities widely present in natural products. Many thienoindole derivatives have biological and pharmacological activities such as bactericidal, antihypertensive, antidepressant, antiallergic, antimalarial, and antitumor, such as 2H-thieno[2,3-b]indole derivatives can be Further transformation produces a compound that controls the activity of rice seedlings. [0003] The synthetic application of thienoindole derivatives has gone beyond the field of medicine and gradually extended to the field of material chemistry, such as electrochemical copolymerization of thienoindole derivatives to prepare high-performance conductive polymers and organic electroluminesce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 李明刘瑞娟文丽荣郭维斯
Owner QINGDAO UNIV OF SCI & TECH
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