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Coumarin compound containing isopropanolamine structure as well as preparation method and application of coumarin compound

A technology of isopropanolamine and coumarins, which is applied in the field of coumarins and their preparation, can solve the problems of increasing the resistance of plant pathogenic microorganisms, endangering crop safety, affecting the environment and the like

Pending Publication Date: 2022-07-15
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of traditional fungicides not only increases the resistance of plant pathogenic microorganisms but also affects the environment and endangers the safety of crops

Method used

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  • Coumarin compound containing isopropanolamine structure as well as preparation method and application of coumarin compound
  • Coumarin compound containing isopropanolamine structure as well as preparation method and application of coumarin compound
  • Coumarin compound containing isopropanolamine structure as well as preparation method and application of coumarin compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0057] Example 1-1: Preparation of 4-(3-bromopropanyl)-2H-benzopyran-2-one

[0058]

[0059] In a 100 mL round-bottomed flask, 4-hydroxycoumarin (18.51 mmol) and 30 mL of DMF were added with stirring to dissolve, then potassium carbonate (18.51 mmol) and 1,3-dibromopropane (36.99 mmol) were added thereto, and the reaction was carried out at room temperature overnight. , TLC tracked the completion of the reaction. After the completion of the reaction, add 90 mL of double distilled water, extract three times with 30 mL of ethyl acetate, combine the organic phases, and then use 50 mL of saturated NH 4 Cl solution and 50 mL saturated NaCl solution were washed once, and the organic phase was washed with anhydrous NaSO 4 dry. Finally, the organic phase was concentrated by rotary evaporation at 45°C, purified and isolated by column chromatography (eluent (V / V): PE / EA=2 / 1) to obtain 4-(3-bromopropanyl)-2H -benzopyran-2-one, white solid, 86.9% yield, m.p.108-109°C; 1 H NMR (400M...

Embodiment 1-2

[0060] Example 1-2: Preparation of tert-butyl 4-(3-((2-oxo-2H-benzopyran-4-yl)oxy)propyl)piperazine-1-carboxylate tert-butyl ester

[0061]

[0062] In a 100 mL round-bottomed flask, 4-(3-bromopropanyl)-2H-benzopyran-2-one (15.89 mmol) was added and dissolved in 30 mL of acetonitrile, and N-Boc piperazine (23.84 mmol) was added thereto. ), potassium carbonate (15.89 mmol) and potassium iodide (1.59 mmol), the reaction was refluxed at 75°C for 16 h, and the completion of the reaction was tracked by TLC. After the completion of the reaction, the reaction was concentrated by rotary evaporation at 45°C, 90 mL of double distilled water was added, extracted twice with 40 mL of ethyl acetate, the organic phases were combined, and then washed twice with 50 mL of saturated NaCl solution, and the organic phase was washed with anhydrous NaSO 4 dry. Finally, it was concentrated with a rotary evaporator at 45°C, purified and isolated by column chromatography (eluent (V / V): DCM / MeOH=20 / ...

Embodiment 1-3

[0063] Example 1-3: Preparation of 4-(3-(piperazin-1-yl)propoxy)-2H-benzopyran-2-one

[0064]

[0065] tert-Butyl 4-(3-((2-oxo-2H-benzopyran-4-yl)oxy)propyl)piperazine-1-carboxylate tert-butyl ester was dissolved in 10 mL of dichloromethane, and then added to 1 mL of trifluoroacetic acid was added thereto, and the reaction was stirred at room temperature for 2 h. After the solvent was removed by rotary evaporation, 4-(3-(piperazin-1-yl)propoxy)-2H-benzopyran-2-one was obtained, and the next experiment was carried out directly.

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Abstract

The invention discloses a coumarin compound containing an isopropanolamine structure, and the coumarin compound containing the isopropanolamine structure is synthesized by taking the coumarin structure as a lead compound and introducing an isopropanolamine fragment. The invention further discloses a preparation method and application of the coumarin compound containing the isopropanolamine structure, and an important scientific basis is provided for research, development and creation of new pesticides.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a coumarin compound containing an isopropanolamine structure and a preparation method and application thereof. Background technique [0002] Plant bacterial and fungal diseases, such as rice bacterial wilt, pepper bacterial wilt, cabbage leaf spot, tobacco bacterial wilt, citrus canker, kiwi fruit canker, cucumber gray mold, pepper fusarium wilt, rapeseed fungus Sclerotinia, wheat scab, late blight of potato, root rot of blueberry, C. vinifera, anthracnose of dragon fruit, sheath blight of rice, etc., are several important diseases caused by plant pathogenic bacteria and fungi and affecting crop production , mainly manifested as necrosis, withering, decay and other symptoms. The use of traditional fungicides not only increases the resistance of plant pathogenic microorganisms but also affects the environment and endangers crop safety. Therefore, there is an urgent n...

Claims

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Application Information

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IPC IPC(8): C07D311/56A01N43/60A01P3/00A01P1/00
CPCC07D311/56A01N43/60
Inventor 杨松冯钰梅周翔王培义吴志兵柳立伟薛伟
Owner GUIZHOU UNIV
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