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Synthesis method of indanone derivatives

A synthesis method and derivative technology, applied in the field of synthesis of indanone derivatives, to achieve the effects of high reaction yield, simple operation, and good economy of atoms and steps

Active Publication Date: 2021-06-11
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the Rh / In and Ir / In catalytic systems, the use of acrylates as reaction substrates to construct indanone-skeleton compounds cannot be achieved.

Method used

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  • Synthesis method of indanone derivatives
  • Synthesis method of indanone derivatives
  • Synthesis method of indanone derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～9

[0055] Add benzoic acid compound (0.3mmol), acrylate compound (0.6mmol), pentamethylcyclopentadiene rhodium dichloride (0.015mmol), sodium acetate (0.3mmol) in test tube according to the raw material ratio of Table 1 ) and organic solvent 0.4ml, mixed and stirred evenly, after the reaction was completed according to the reaction conditions in Table 2, cooling, suction filtration, silica gel mixing sample, and obtaining the corresponding 2-substituted indanone compound (I) through column chromatography purification;

[0056] The reaction process is shown in the following formula:

[0057]

[0058] The raw material ratio of table 1 embodiment 1~9

[0059]

[0060] The reaction conditions and reaction result of table 2 embodiment 1~9

[0061]

[0062]

[0063] In Table 2, T is the reaction temperature, and t is the reaction time.

Embodiment 10

[0065] Add 2-substituted indanone derivative (I-1) (0.3mmol), sodium acetate (0.3mmol), and hexafluoroisopropanol (HFIP) 0.4ml into the test tube, mix and stir evenly under nitrogen, place in React in an oil bath at 150°C for 18 hours. After completion of the reaction, cooling, suction filtration, sample mixing with silica gel, purification by column chromatography to obtain the corresponding non-substituted indanone compound (I-10), the reaction process is shown in the following formula:

[0066]

[0067] The data characterization of indanone compound (I) is as follows: Figure 1-10 As shown, wherein, the hydrogen spectrum is tested on a 400MHz nuclear magnetic instrument; the carbon spectrum is tested on a 100MHz nuclear magnetic instrument; the test conditions are all using tetramethylsilane as an internal standard at room temperature, and the sample is dissolved in deuterated chloroform.

[0068] The structures and relevant data of some compounds prepared in Examples 1-1...

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Abstract

The present invention provides a synthesis method of indanone derivatives. The synthesis method comprises the following steps: adding a benzoic acid compound, an acrylate compound, a rhodium catalyst and an alkali to an organic solvent, heating under a nitrogen gas condition to carry out a reaction, and after the reaction is complete, carrying out post-treatment to obtain 2-substituted indanone compounds. According to the synthesis method of the indanone derivatives, one-step synthesis of the indanone products from the benzoic acid compound and the acrylic ester compound is realized; and the method is simple and convenient to operate, good in functional group compatibility and high in reaction yield.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of indanone derivatives. Background technique [0002] Indanones are an important class of skeletons, and their derivatives are widely found in natural products and drug molecules. In addition, indanones are also very useful intermediates that can be used to synthesize different types of compounds. Therefore, it has received more and more attention in organic synthesis. The traditional methods for synthesizing indanones mainly include Friedel-Crafts acylation and Nazarov cyclization. However, the conditions of these reactions are relatively harsh, and they need to be carried out under strong acid conditions, and the substrates need to be prefunctionalized, which leads to cumbersome synthesis steps. Therefore, it is necessary to develop more convenient and efficient methods to synthesize indanone derivatives. [0003] In recent years, t...

Claims

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Application Information

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IPC IPC(8): C07C69/757C07C67/313C07C253/30C07C255/47C07C45/65C07C49/67
CPCC07C67/313C07C253/30C07C45/65C07C2602/08C07C69/757C07C255/47C07C49/67
Inventor 张玉红于书玲刘占祥
Owner ZHEJIANG UNIV
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