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Indole derivative and preparation method thereof

A technology of indole derivatives and compounds, applied in the field of indole derivatives and their preparation, can solve the problems of complex structure, heavy metal pollution, and inability to recycle, and achieve high reference value, mild conditions, and easy operation

Active Publication Date: 2019-09-20
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods all rely on iridium or ruthenium photocatalysts, which are expensive, complex in structure, unable to be recycled, and have the problem of heavy metal pollution, which is not conducive to the expansion and application of the reaction.

Method used

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  • Indole derivative and preparation method thereof

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preparation example Construction

[0028] A kind of preparation method of indole derivative provided by the present invention comprises the following steps:

[0029] Reacting a mixture of one of the compounds represented by formula I, an additive and a solvent under conditions of nitrogen or argon and visible light to obtain an indole derivative;

[0030] The structural formula of the compound shown in the formula I is as follows:

[0031]

[0032] Among them, R 1 One selected from hydrogen, methyl, ethyl, cyclopropyl, cyclohexyl, phenyl, 4-methylphenyl, 4-chlorophenyl, 3-chlorophenyl or 3-methoxyphenyl ;

[0033] R 2 One selected from hydrogen, chlorine, bromine, methoxy or cyano.

[0034] The synthetic route is as follows:

[0035]

[0036] In the preparation method of indole derivatives provided by the present invention, in a nitrogen or argon atmosphere, visible light irradiation can excite the compound shown in formula I to undergo homolysis of the carbon-oxygen bond, and then [1,6]-H migration ...

Embodiment 1

[0048]

[0049] In a 10mL quartz test tube, add p-toluenesulfonic acid (4.0mg, 0.02mmol), 2-pyrrolidinylbenzaldehyde (35.0mg, 0.2mmol), N-methylpyrrolidone (2mL), argon protection, blue LED Under lamp irradiation, stir at room temperature for 24 hours. After the reaction was completed, N-methylpyrrolidone was removed by washing with water, and the product (14.1 mg, yield 47%) was obtained by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate as the eluent.

[0050] 1 H NMR (400MHz, CDCl3) δ7.57(d, J=7.8Hz, 1H), 7.27(d, J=8.0Hz, 1H), 7.14(t, J=7.0Hz, 1H), 7.08(t, J =7.0Hz,1H),6.19(s,1H),4.09(t,J=7.0Hz,2H),3.05(t,J=7.4Hz,2H),2.71–2.55(m,2H).

[0051] 13 C NMR (100MHz, CDCl 3 )δ144.61, 133.30, 132.70, 120.33, 120.14, 119.13, 109.41, 92.31, 43.62, 27.88, 24.32.

Embodiment 2

[0053]

[0054] According to the same method as in Example 1, the product (21.2 mg, yield 45%) was obtained using 5-bromo-2-pyrrolidinylbenzaldehyde (50.8 mg, 0.2 mmol) as the reaction raw material.

[0055] 1 H NMR (400MHz, CDCl3) δ7.64(s, 1H), 7.17(d, J=8.5Hz, 1H), 7.07(d, J=8.5Hz, 1H), 6.09(s, 1H), 4.02(t ,J=6.9Hz,2H),3.00(t,J=7.4Hz,2H),2.71–2.52(m,2H).

[0056] 13 C NMR (100MHz, CDCl 3 )δ145.99, 134.87, 131.33, 122.84, 122.71, 112.38, 110.71, 92.14, 43.81, 27.79, 24.39

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Abstract

The invention provides an indole derivative and a preparation method thereof. The preparation method includes the following steps: mixing a compound shown in a formula I, an additive and a solvent, carrying out a reaction under the conditions of nitrogen or argon and visible light to obtain the indole derivative. In the atmosphere of nitrogen or argon, the compound of the formula I is excited by visible light to be subjected to homolysis of a carbon-oxygen bond, [1,6]-H transfer is carried out, and finally the indole derivative is synthesized by intramolecular free radical coupling and a dehydration reaction. The whole process does not need the participation of a photocatalyst, has the advantages of simple operation, mild condition and high yield, is in line with atomic economy and environmental protection, and has high reference value for industrial preparation of the indole derivative.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an indole derivative and a preparation method thereof. Background technique [0002] As a star molecular skeleton, the core of indole derivatives widely exists in organic intermediates, natural products and drugs, and has a wide range of pharmacological activities and research potential. Therefore, the synthesis of multi-substituted indole derivatives through fast, simple and efficient methods has always been the direction of people's efforts. [0003] Visible light-induced photoredox reactions have attracted extensive attention of researchers in recent years because they can provide novel and efficient synthetic strategies for the synthesis of complex organic molecules under mild conditions. Rueping et al reported the photoredox reaction mediated by iridium under visible light, and synthesized a series of indole derivatives (S.Q. Zhu, A. Das, L. Bui, H.J. Zhou, D.P. ...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D209/08C07D471/04
CPCC07D209/08C07D471/04C07D487/04
Inventor 位文涛周经纬黄凯鹏王奇
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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