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A kind of preparation method of 3-selenocoumarin compound

A technology for substituting coumarin and coumarin, which is applied in the field of organic synthesis, and achieves the effects of simple preparation method, simple operation and high yield

Active Publication Date: 2021-04-20
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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  • A kind of preparation method of 3-selenocoumarin compound
  • A kind of preparation method of 3-selenocoumarin compound
  • A kind of 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 3-selenocoumarin compounds, comprising: using PIFA as an oxidant in a DCM solvent, using coumarin compounds and selenoether compounds as substrates, and synthesizing at room temperature 3‑Selenocoumarins. The invention has cheap and easy-to-obtain reaction raw materials, simple preparation method, uses PIFA as an oxidant, has low reaction cost, short reaction time, high yield and simple operation, and is suitable for the synthesis of different types of 3-selenocoumarin compounds. The method of the invention can be used to synthesize a series of 3-selenocoumarin compounds, and the synthesized products can not only be used as intermediate compounds, but also be used to further construct complex active compounds; meanwhile, the compounds have great potential for drug activity.

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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Patent Type & Authority Patents(China)
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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