Preparation method of 3-selenocoumarin compound

A technology for substituting coumarins and coumarins, which is applied in the field of organic synthesis to achieve the effects of high yield, simple operation and low reaction cost

Active Publication Date: 2019-11-22
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To the best of our knowledge, there is currently no direct regioselective method for the selenization of the carbon three position of the coumarin backbone

Method used

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  • Preparation method of 3-selenocoumarin compound
  • Preparation method of 3-selenocoumarin compound
  • Preparation method of 3-selenocoumarin compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Add coumarin (0.2mmol), 1,2-diphenyl diselenide (0.4 mmol), PIFA (0.4mmol), TMSN 3 (Azidotrimethylsilane) (0.4 mmol) and toluene (toluene) (2.0 mL), stirred at room temperature. TLC tracking detection reaction. After 12 hours, the starting material had been partially converted. Water and dichloromethane were added to the reaction system, and the organic layer was separated. The aqueous layer was washed twice with dichloromethane, all organic layers were combined and washed twice with water. The organic layer was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (10% ethyl acetate petroleum ether solution) to obtain 45.1 mg of product with a yield of 75%. The reaction process is shown in the following formula:

[0039]

[0040] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0041] 1 H NMR (500MHz, DMSO-d 6 )δ7.70–7.68(m,2H),7.56–7.47(m,5H),7.42(s,1H),7.40(d,J=8.3Hz,1H),7.29...

Embodiment 2

[0043] Add coumarin (0.2mmol), 1,2-diphenyl diselenide (0.4 mmol), PIFA (0.4mmol), TMSN 3(0.4 mmol) and MeCN (acetonitrile) (2.0 mL), stirred at room temperature. TLC tracking detection reaction. After 0.5 hour, the starting material was completely converted. Water and dichloromethane were added to the reaction system, and the organic layer was separated. The aqueous layer was washed twice with dichloromethane, all organic layers were combined and washed twice with water. The organic layer was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (10% ethyl acetate petroleum ether solution) to obtain 53.6 mg of product with a yield of 89%. The reaction process is shown in the following formula:

[0044]

[0045] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0046] 1 H NMR (500MHz, DMSO-d 6 )δ7.70–7.68(m,2H),7.56–7.47(m,5H),7.42(s,1H),7.40(d,J=8.3Hz,1H),7.29–7.25(m,1H)ppm; 13 C NMR ...

Embodiment 3

[0048] Add coumarin (0.2mmol), 1,2-diphenyl diselenide (0.4 mmol), PIFA (0.4mmol), TMSN 3 (0.4mmol) and DCM (2.0mL), stirred at room temperature. TLC tracking detection reaction. After 0.5 hour, the starting material was completely converted. Water and dichloromethane were added to the reaction system, and the organic layer was separated. The aqueous layer was washed twice with dichloromethane, all organic layers were combined and washed twice with water. The organic layer was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (10% ethyl acetate petroleum ether solution) to obtain 59.0 mg of product with a yield of 98%. The reaction process is shown in the following formula:

[0049]

[0050] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0051] 1 H NMR (500MHz, DMSO-d 6 )δ7.70–7.68(m,2H),7.56–7.47(m,5H),7.42(s,1H),7.40(d,J=8.3Hz,1H),7.29–7.25(m,1H)ppm; 13 C NMR (126MHz, DMSO-d ...

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Abstract

The invention discloses a preparation method of a 3-selenocoumarin compound, which comprises the following steps: in a DCM solvent, synthesizing to obtain the 3-selenocoumarin compound at room temperature by using PIFA as an oxidant and using a coumarin compound and a selenide compound as substrates. According to the method, the reaction raw materials are cheap and easy to obtain, the preparationmethod is simple, PIFA is used as an oxidizing agent, the reaction cost is low, the reaction time is short, the yield is high, the operation is simple, and the method is suitable for synthesizing different types of 3-selenocoumarin compounds. The method disclosed by the invention can be used for synthesizing a series of 3-selenocoumarin compounds, and the synthesized product can be used as an intermediate compound for further constructing a complex active compound; meanwhile, the compound has great drug activity potential.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing 3-selenocoumarin compounds through regioselective selenization. Background technique [0002] As the core skeleton, coumarin and its derivatives are widely distributed in natural products and active pharmaceutical molecules. Meanwhile, due to the optical activity of such compounds, they play an important role in organic materials. Among many coumarin derivatives, 3-substituted coumarin compounds have received extensive attention due to their proven anti-inflammatory, anti-oxidation, anti-HIV, anti-cancer, antibacterial and other biological activities. Due to the important applications of 3-substituted coumarins in different fields, the synthetic methods of these compounds have been extensively explored. [0003] Prefunctionalized reactant coupling is the traditional method for preparing 3-substituted coumarins. In recent years, direct carbon-...

Claims

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Application Information

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IPC IPC(8): C07D311/12C07D311/56C07D311/14C07D311/16C07D311/92C07D405/12
CPCC07D311/12C07D311/14C07D311/16C07D311/56C07D311/92C07D405/12
Inventor 宋增强丁超超王绍丽盛耀光戴倩梁广
Owner WENZHOU MEDICAL UNIV
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