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Preparation method of seleno-flavonoid compounds

A technology of chromone compounds and selenoflavones, which is applied in organic chemistry and other fields, can solve the problems of narrow substrate range and achieve the effects of short reaction time, high yield and mild reaction conditions

Active Publication Date: 2019-01-11
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the synthetic methods of selenoflavonoids. At present, there is only one reported method, which is completed by the direct carbon-hydrogen functionalization of chromone and the reaction of aryl diselenides.
In this method, 1 equivalent of aryl diselenide is used, ammonium iodide is used as a promoter, the reaction is carried out at 135 °C, the reaction time is 12 hours, and the reported substrate range is narrow

Method used

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  • Preparation method of seleno-flavonoid compounds
  • Preparation method of seleno-flavonoid compounds
  • Preparation method of seleno-flavonoid compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add chromone (0.2mmol), 1,2-diphenyldiselenide (0.1 mmol), NIS (0.04mmol), TBHP (0.8mmol) and DMF (2.0mL) into a 5mL reaction flask respectively, and stir at 70°C. TLC tracking detection reaction. After 7 hours, the reaction was stopped. Water and ethyl acetate were added to the reaction system, and the organic layer was separated. The aqueous layer was washed twice with ethyl acetate, 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 56.6 mg of the product (CAS No.: 1980869-97-3), with a yield of 94%. The process is as follows:

[0028]

[0029] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0030] 1 H NMR (500MHz, DMSO-d 6 )δ8.61(s,1H),8.07(dd,J=8.0,1.4Hz,1H),7.85(dd,J=11.3,4.3Hz,1H),7.68(dd,J=8.5,0.6Hz,1H ),7.55–7.52 (m,1H),7.47–7.4...

Embodiment 2

[0032] Add chromone (0.2mmol), 1,2-diphenyldiselenide (0.1 mmol), NIS (0.04mmol), TBHP (0.8mmol) and DMSO (2.0mL) into a 5mL reaction flask respectively, and stir at 70°C. TLC tracking detection reaction. After 12 hours, the reaction was stopped. Water and ethyl acetate were added to the reaction system, and the organic layer was separated. The aqueous layer was washed twice with ethyl acetate, 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 27.1 mg of product with a yield of 45%. The reaction process is shown in the following formula:

[0033]

[0034] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0035] 1 H NMR (500MHz, DMSO-d 6 )δ8.61(s,1H),8.07(dd,J=8.0,1.4Hz,1H),7.85(dd,J=11.3,4.3Hz,1H),7.68(dd,J=8.5,0.6Hz,1H ),7.55–7.52 (m,1H),7.47–7....

Embodiment 3

[0037] Add chromone (0.2mmol), 1,2-diphenyldiselenide (0.1 mmol), NIS (0.04mmol), TBHP (0.8mmol) and DCM (2.0mL) into a 5mL reaction flask respectively, and stir at 70°C. TLC tracking detection reaction. After 12 hours, the reaction was stopped. Water and ethyl acetate were added to the reaction system, and the organic layer was separated. The aqueous layer was washed twice with ethyl acetate, 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 12.6 mg of product with a yield of 21%. The reaction process is shown in the following formula:

[0038]

[0039]Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0040] 1 H NMR (500MHz, DMSO-d 6 )δ8.61(s,1H),8.07(dd,J=8.0,1.4Hz,1H),7.85(dd,J=11.3,4.3Hz,1H),7.68(dd,J=8.5,0.6Hz,1H ),7.55–7.52 (m,1H),7.47–7.44...

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Abstract

The invention discloses a preparation method of seleno-flavonoid compounds. The preparation method comprises the step of preparing the seleno-flavonoid compounds through direct compounding of hydrocarbon functional groups in substrates (chromone compounds and diselenide compounds) in a DMF solvent in the presence of an accelerant NIS / TBHP. The preparation method has the beneficial effects that thereaction raw materials are cheap and easily available, and the preparation method is simple; the synthetic method of the use amount of diselenide is 0.5, and meanwhile, the cheap and easily availablenon-metal reagent NIS / TBHP is taken as the reaction accelerant, so that the method is an environment-friendly and atom-economic synthetic method. The reaction is carried out at 70 DEG C, the reactiontime is short, the yield is high, and the operation is simple. The method can be used for synthesizing a series of the seleno-flavonoid compounds, and a synthesized product can be taken as an intermediate product and can be used for further constructing complex active compounds; and meanwhile, the compounds have 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 selenoflavonoids promoted by NIS / TBHP. Background technique [0002] In recent years, due to the wide application of selenium-containing compounds in the fields of chemical biology, synthetic chemistry, agricultural chemistry, food chemistry and materials science, the research of this kind of compounds has received extensive attention. Especially heterocyclic compounds containing selenium, which have a wide range of biological activities, such as anti-tumor activity, anti-inflammatory activity, antiviral activity, antioxidant activity and antibacterial activity, such compounds widely exist as the core skeleton and active pharmaceutical molecules . Therefore, the method of selenization of heterocyclic compounds is very important in modern organic synthesis, and a large number of chemical methods for constructing carbon-selenium bonds have been d...

Claims

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Application Information

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IPC IPC(8): C07D311/12C07D311/16C07D311/92C07D405/12C07D407/12C07D409/12
CPCC07D311/12C07D311/16C07D311/92C07D405/12C07D407/12C07D409/12
Inventor 宋增强詹玲玲丁超超于源祖张文歆钱建畅梁广
Owner WENZHOU MEDICAL UNIV
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