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Preparation method of polysubstituted indanone derivative

A compound and reaction technology, applied in the field of multi-substituted indanone derivatives and its preparation, can solve problems such as complex operation, difficult preparation of raw materials, and many reaction steps

Active Publication Date: 2020-10-23
XIAMEN HUAXIA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above methods usually require the use of expensive transition metals and have disadvantages such as low regioselectivity, difficult preparation of raw materials, high cost, large pollution, many reaction steps, harsh reaction conditions, and complicated operations.

Method used

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  • Preparation method of polysubstituted indanone derivative
  • Preparation method of polysubstituted indanone derivative
  • Preparation method of polysubstituted indanone derivative

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specific Embodiment approach

[0028] In order to enable those skilled in the art to better understand the technical solutions of the present invention, some non-limiting examples are further disclosed below to further describe the present invention in detail.

[0029] The reagents used in the present invention can be purchased from the market or can be prepared by the methods described in the present invention.

Embodiment 1

[0031]

[0032] Add 2.0mmol of the compound of formula (4), 0.5mmol of the compound of formula (5), and 2.0mL of acetonitrile into a 10mL reaction tube, place it in an oil bath at 140°C under the irradiation of a 250W UV lamp with a maximum wavelength of 365nm, and react for 48h . Stop the reaction, cool to room temperature, add dichloromethane to dilute, extract with water three times, dry the organic phase with anhydrous sodium sulfate, filter, and the filtrate is separated by column chromatography to obtain 120 mg of the compound of formula (6), with a yield of 85% and a purity of 99.5 %. The NMR characterization of this compound is as follows: 1 HNMR (400MHz, CDCl 3 )δ7.59(d,J=7.0Hz,1H),7.46–7.33(m,6H),7.31–7.22(m,6H),7.15(d,J=7.2Hz,1H); 13 C NMR (100MHz, CDCl 3 )δ196.5, 155.3, 145.2, 134.9, 133.4, 132.7, 132.4, 130.7, 130.0, 129.3, 128.9, 128.8, 128.5, 128.0, 127.7, 123.0, 121.2.

Embodiment 2

[0034] Add 2.0mmol of the compound of formula (4), 0.5mmol of the compound of formula (5), and 2.0mL of acetonitrile into a 10mL reaction tube, place it in an oil bath at 140°C under the irradiation of a 25W UV lamp with a maximum wavelength of 365nm, and react for 48h . Stop the reaction, cool to room temperature, add dichloromethane to dilute, extract with water three times, the organic phase is dried with anhydrous sodium sulfate, filtered, and the filtrate is separated by column chromatography to obtain 11 mg of the compound of formula (6), with a yield of 8%.

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Abstract

The invention relates to a polysubstituted indanone derivative and a preparation method thereof, and belongs to the technical field of organic synthesis. The preparation method comprises the followingsteps: in a solvent, reacting aryl aldehyde with an alkyne derivative under an illumination condition, and carrying out post-treatment to generate the polysubstituted indanone derivative. The methodhas the advantages of simple operation, environmental friendliness, high regioselectivity, low cost, mild reaction conditions, simple operation, wide substrate range, simple post-treatment, high yield, high purity and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a polysubstituted indanone derivative and a preparation method thereof. Background technique [0002] Multi-substituted indanone compounds have many important biological activities such as sterilization, anti-inflammation, anti-virus, anti-cancer, anti-depression, etc., and are widely used in natural products, medicine, pesticides and other fields. Therefore, the research on new synthetic methods of multi-substituted indanone compounds and their analogues has important application value and has attracted the attention of researchers in related fields. [0003] At present, the method of synthesizing indanone is mainly prepared by the catalytic reaction of transition noble metals such as palladium, rhodium, ruthenium, such as palladium, rhodium, ruthenium catalyzed carbon-hydrogen activation, palladium catalyzed intramolecular aldol condensation, palladium cat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/00C07C49/563C07C49/567
CPCC07C45/00C07C2602/08C07C49/563C07C49/567
Inventor 冯亚栋肖玉娟傅奇
Owner XIAMEN HUAXIA UNIV
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