Preparation method of poly-substituted diphenylethylene indole derivative

A technology of stilbene derivatives and stilbene, which is applied in the field of preparation of stilbene stilbene derivatives, can solve problems such as long reaction time, and achieve short reaction time, high yield, and high environmental friendliness Effect

Active Publication Date: 2019-04-26
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Obvious disadvantages of the above-mentioned processes for the preparation of vinylindole derivatives: longer reaction times, use of toxic solvents such as toluene or tetrahydrofuran

Method used

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  • Preparation method of poly-substituted diphenylethylene indole derivative
  • Preparation method of poly-substituted diphenylethylene indole derivative
  • Preparation method of poly-substituted diphenylethylene indole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of Distyrylindole Derivative 3aa

[0022]

[0023] Add N-methoxyindolecarboxamide 1a (0.1mmol, 19.0mg), 2a (0.1mmol, 17.8mg), dichlorobis(4-methylisopropylphenyl) into a 15ml thick-walled pressure-resistant tube Ruthenium(Ⅱ) (0.005mmol, 3.1mg) and sodium acetate (0.2mmol, 27.2mg) were added to water:dichloromethane (1.0mL, 9:1), stirred at room temperature, and reacted for 3 hours. After the reaction is complete, use a rotary evaporator to remove the solvent to obtain a crude product, which is separated by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=4 / 1), and uses a rotary evaporator to remove the solvent to obtain the target The yield of the unsubstituted distyrylindole derivative 3aa was 99%.

[0024] Spectrum analysis data 3aa:

[0025] 1 H NMR (400MHz, DMSO-d 6 )δ11.53(s,1H),10.44(s,1H),7.51(d,J=7.8Hz,1H),7.32(d,J=8.1Hz,1H),7.24(dd,J=5.0,1.7 Hz,3H),7.20–7.13(m,3H),7.09–7.02(m,5H),7.00–6.94(m,1H),6.68(d,J=1.5Hz,1...

Embodiment 2

[0027] Replace 1a in Example 1 with 1b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0028]

[0029] Spectrum analysis data 3ba:

[0030] 1 H NMR (400MHz, DMSO-d 6 )δ11.57(s,1H),10.68(s,1H),7.73(d,J=1.7Hz,1H),7.29(d,J=8.6Hz,1H),7.24(dd,J=5.0,1.6 Hz,3H),7.18(d,J=1.9Hz,2H),7.16(d,J=3.0Hz,2H),7.09–7.02(m,4H),6.68(d,J=1.6Hz,1H), 3.42(s,3H). 13 C NMR (101MHz, DMSO-d 6 ( 24 h 19 BrN 2 NaO 2 + [M+Na] + 469.0528,found 469.0528.

Embodiment 3

[0032] Replace 1a in Example 1 with 1c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0033]

[0034] Spectrum analysis data 3ca:

[0035] 1 H NMR (400MHz, DMSO-d 6 )δ11.56(s,1H),10.67(s,1H),7.59(d,J=2.0Hz,1H),7.33(d,J=8.6Hz,1H),7.25(dd,J=5.0,1.7 Hz,3H),7.19(s,1H),7.16(d,J=2.6Hz,2H),7.05(ddt,J=7.4,3.3,1.7Hz,5H),6.68(d,J=1.5Hz,1H ),3.42(s,3H). 13 C NMR (101MHz, DMSO-d 6 ( 24 h 19 ClN 2 NaO 2 ++ [M+Na] + 425.1033, found 425.1028.

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Abstract

The invention discloses a preparation method of a novel poly-substituted diphenylethylene indole derivative and belongs to the technical field of organic synthesis. The method comprises the followingsteps: adding substituted N-methoxy indole formamide, diphenyl acetylene, dichloro-bi(4-methyl isopropyl phenyl)ruthenium (II) and sodium acetate into a reactor. After the stirring and the reacting are finished in a solvent, a rotary evaporator is used for concentrating a filtrate to obtain a crude product, and the crude product is separated through silica gel column chromatography to obtain a target compound. The provided synthesis method of the poly-substituted diphenylethylene indole derivative has the characteristics that the synthesis method is scientific, reasonable and simple, the yieldof the target compound is high, the product is easy to purify, the reaction time is relatively short, the reaction condition is room-temperature aqueous phase, and the synthesis method is environmentally friendly. The reaction equation is as shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of distyrylindole derivatives. Background technique [0002] Nitrogen-containing heterocycles are widely found in natural products and molecules with biological and pharmaceutical activities. Among these heterocyclic compounds, vinylindole compounds play an indispensable role in drug design and synthesis. For example, antineoplastic drugs, anti-infective drugs, and anti-inflammatory drugs all contain molecular fragments of vinyl indole. ((a) WO2008122620A1. (b) WO2014033597A1.) [0003] In view of the wide biological activity and application value of vinyl indole derivatives, it is of great significance to develop a new method for the practical and effective synthesis of vinyl indole derivatives. [0004] The methods for synthesizing vinyl indole derivatives are: [0005] 1) In 2006, Nakao and Hiyama's research group reported the syn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 张林宝朱明辉姚天宇文丽荣李明
Owner QINGDAO UNIV OF SCI & TECH
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