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Preparation method of 5-maleimide chromone compound

A technology for maleimide chromone and chromone compounds, which is applied in the field of ruthenium-catalyzed preparation of 5-maleimide chromone compounds, which can solve the problems of inability to carry out β hydrogen and elimination, and achieve the reaction time Short, high-yield, easy-to-operate results

Active Publication Date: 2019-12-20
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this strategy, the reaction intermediate has no β hydrogen on the syn face, and cannot undergo β hydrogen elimination, so there is no direct synthesis of 5-maleimide chromone through this strategy.

Method used

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  • Preparation method of 5-maleimide chromone compound
  • Preparation method of 5-maleimide chromone compound
  • Preparation method of 5-maleimide chromone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] At room temperature, chromone (0.2mmol), N-ethylmaleimide (0.5mmol), [Ru(p-cymene)Cl 2 ] 2 (5mol%), AgNTf 2 (20mol%), silver acetate (3 equiv.) and DCE (2.0 mL). Raise the temperature to 120°C and stir. TLC tracking detection reaction. After 1 hour, the reaction was stopped. Water and ethyl acetate were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three times with ethyl acetate. Combine all organic layers, dry with anhydrous sodium sulfate, concentrate, and separate by column chromatography (40% ethyl acetate petroleum ether solution), obtain product 49.5mg, productive rate is 92%, reaction process is shown in the following formula:

[0030]

[0031] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0032] 1 H NMR (400MHz, CDCl 3 )δ7.83(d, J=6.0Hz, 1H), 7.71–7.67(m, 1H), 7.57(d, J=8.5Hz, 1H), 7.22(d, J=7.3Hz, 1H), 6.42( s, 1H), 6.28 (d, J = 6.0Hz, 1H), 3.63 (q, ...

Embodiment 2

[0034] At room temperature, chromone (0.2mmol), N-ethylmaleimide (0.5mmol), [Ru(p-cymene)Cl 2 ] 2 (5mol%), AgNTf 2 (20mol%), silver acetate (3 equiv.) and chlorobenzene (2.0 mL). Raise the temperature to 120°C and stir. TLC tracking detection reaction. After 3.5 hours, the reaction was stopped. Water and ethyl acetate were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three times with ethyl acetate. Combine all organic layers, dry with anhydrous sodium sulfate, concentrate, and separate by column chromatography (40% ethyl acetate petroleum ether solution), obtain product 45.2mg, yield rate is 84%, and reaction process is shown in the following formula:

[0035]

[0036] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0037] 1 H NMR (400MHz, CDCl 3 )δ7.83(d, J=6.0Hz, 1H), 7.71–7.67(m, 1H), 7.57(d, J=8.5Hz, 1H), 7.22(d, J=7.3Hz, 1H), 6.42( s, 1H), 6.28 (d, J = 6.0Hz, 1H...

Embodiment 3

[0039] At room temperature, chromone (0.2mmol), N-ethylmaleimide (0.5mmol), [Ru(p-cymene)Cl 2 ] 2 (5mol%), AgNTf 2 (20mol%), silver acetate (3 equiv.) and ethyl acetate (2.0 mL). Raise the temperature to 120°C and stir. TLC tracking detection reaction. After 3.5 hours, the reaction was stopped. Water and ethyl acetate were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three times with ethyl acetate. Combine all organic layers, dry with anhydrous sodium sulfate, concentrate, and separate by column chromatography (40% ethyl acetate petroleum ether solution), obtain product 30.7mg, productive rate is 57%, and reaction process is shown in the following formula:

[0040]

[0041] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0042] 1 H NMR (400MHz, CDCl 3 )δ7.83(d, J=6.0Hz, 1H), 7.71–7.67(m, 1H), 7.57(d, J=8.5Hz, 1H), 7.22(d, J=7.3Hz, 1H), 6.42( s, 1H), 6.28 (d, J = 6.0H...

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Abstract

The invention discloses a preparation method of a 5-maleimide chromone compound. The preparation method comprises the steps that in a DCE solvent, [Ru(p-cymene)Cl2]2 and AgNTf2 are used as catalysts,silver acetate serves as an additive, a maleimide compound and a chromone compound are taken as substrates, and the 5-maleimide chromone compound is synthesized. According to the preparation method ofthe 5-maleimide chromone compound, the reaction raw materials are low in cost and easy to obtain, the preparation method is simple, ruthenium is used as a catalyst, the reaction cost is low, the reaction time is short, the yield is high, operation is easy, and the preparation method is suitable for synthesis of different types of 5-maleimide chromone compounds. The preparation method can be usedfor synthesizing a series of 5-maleimide chromone compounds, and synthesized products can serve as intermediate compound, and can also be used for further constructing complex active compounds; and meanwhile, the compounds have great medicine activity potential.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a ruthenium-catalyzed method for preparing 5-maleimide chromone compounds. Background technique [0002] Maleimide derivatives have a variety of biological activities, and they are widely distributed in natural products and pharmaceutically active molecules as cores. Therefore, the synthesis of maleimide derivatives has been extensively studied. Transition metal-catalyzed carbon-hydrogen bond activation is considered to be a direct and efficient method for the synthesis of heterocyclic compounds. In the past few decades, methods for the coupling of maleimides and heterocycles based on transition-metal-catalyzed carbon-hydrogen bond activation strategies have been largely developed. For the olefination of maleimide assisted by the positioning group, since the reaction intermediate has no β-hydrogen on the syn face, β-hydrogen elimination cannot be performed, so the p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04
CPCC07D405/04
Inventor 宋增强梁广
Owner WENZHOU MEDICAL UNIV
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