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Method for synthesizing 2,4-dialkylene-substituted indole compound with one-pot process

A technology of indole compounds and dienyl, applied in the field of one-pot synthesis of 2,4-dienyl-substituted indole compounds, can solve the optical properties of 2,4-dienyl-substituted indole, which is rarely studied, etc. problem, to achieve the effects of strong substrate design, high reaction yield and mild reaction conditions

Inactive Publication Date: 2017-05-10
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, small molecule organic fluorescent compounds have gradually attracted people's attention, and the optical properties of 2,4-dienyl substituted indoles have been rarely studied so far.

Method used

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  • Method for synthesizing 2,4-dialkylene-substituted indole compound with one-pot process
  • Method for synthesizing 2,4-dialkylene-substituted indole compound with one-pot process
  • Method for synthesizing 2,4-dialkylene-substituted indole compound with one-pot process

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Experimental program
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Effect test

Embodiment 1～10

[0046] Add indole carboxylic acid (0.1mmol), vinyl compound (0.4mmol), [Cp*RhCl 2 ] 2 (0.005mmol), basic copper carbonate (0.21mmol), silver hexafluoroantimonate (0.02mmol), potassium acetate (0.1mmol) and 1ml of organic solvent, mix and stir evenly, after the reaction is completed according to the reaction conditions in Table 2, extract , washed, dried, sample mixed with silica gel, purified by column chromatography to obtain the corresponding 2,4-dienyl substituted indole compound (I), the reaction process is shown in the following formula:

[0047]

[0048] The raw material ratio of table 1 embodiment 1~10

[0049]

[0050]

[0051] The reaction conditions and reaction result of table 2 embodiment 1~10

[0052]

[0053] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, COOMe is methoxycarbonyl, OMe is methoxy, CF 3 is trifluoromethyl, Ph is phenyl.

[0054] The structure confirmation data of some compounds prepared in Examples 1-...

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Abstract

The invention discloses a method for synthesizing a 2,4-dialkylene-substituted indole compound with a one-pot process. The method comprises steps as follows: indolecarboxylic acid, ethylene compounds, [Cp*RhCl2]2(pentamethylcyclopentadienerhodium chloridedimer), alkaline copper carbonate, potassium acetate and silver hexafluoroantimonate are added to an organic solvent and heated for a reaction, aftertreatment is performed after a complete reaction, and the 2,4-dialkylene-substituted indole compound is obtained. According to the method, with the adoption of specific catalysts and the alkaline additive, C-H bonds of indolecarboxylic acid and ethylene compounds are subjected to activation, alkylation and decarboxylation reactions at the same time, the operation conditions are simple, and the reaction yield is high.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing 2,4-dienyl-substituted indole compounds in one pot and an application thereof. Background technique [0002] Indole compounds are the most widely distributed heterocyclic compounds in nature. As intermediates of medicines, pesticides, dyes and other fine chemical products, they are used more and more widely. In recent years, organic fluorescent materials have become one of the most active research topics in the field of luminescent materials. Indole is a fluorescent reagent excited by ultraviolet light. Due to its significant fluorescence shift change, indole can be applied to dual-wavelength ratiometric experiments, which can avoid problems such as uneven dyeing and photofading, and has been widely used. The present invention revolves around this field, selects the indole chromophoric group with charge-donating ability as the main structura...

Claims

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Application Information

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IPC IPC(8): C07D209/24C07D209/08C07D209/10C09K11/06
CPCC07D209/08C07D209/10C07D209/24C09K11/06C09K2211/1029
Inventor 陈辉林聪刘占祥张玉红
Owner ZHEJIANG UNIV
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