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N-substituent-3-[3-(substituted phenyl)-2-allyl-1- ketone]-4-hydroxypyrroline-2-ketone compound as well as preparation method and application thereof

A technology of hydroxypyrroline and ketone compounds, applied in botany equipment and methods, applications, organic chemistry, etc., can solve the problem of low activity against tobacco mosaic virus, etc., and achieve the effect of low cost and easy synthesis

Active Publication Date: 2014-08-27
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, no one has reported about the compounds with natural pyrroline as the basic skeleton and the structure of 1,4-pentadien-3-one, and there are relatively few reports on the anti-tobacco mosaic virus activity of such compounds at home and abroad. few

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  • N-substituent-3-[3-(substituted phenyl)-2-allyl-1- ketone]-4-hydroxypyrroline-2-ketone compound as well as preparation method and application thereof
  • N-substituent-3-[3-(substituted phenyl)-2-allyl-1- ketone]-4-hydroxypyrroline-2-ketone compound as well as preparation method and application thereof
  • N-substituent-3-[3-(substituted phenyl)-2-allyl-1- ketone]-4-hydroxypyrroline-2-ketone compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment one, N - Preparation of p-tolyl-3-[3-(2,3-dichlorophenyl)-2-en-1-one]-4-hydroxypyrrolin-2-one (compound number I1).

[0032] first step: N - Preparation of p-methylphenylglycine ethyl ester:

[0033] Add 0.55 g (5 mmol) of p-toluidine, 0.73 g (6 mmol) of ethyl chloroacetate, 10 mL of 95% ethanol, and 0.49 g (5 mmol) of sodium acetate into a 50 mL three-neck flask. Heat to reflux for 6 h, add 20 mL of water after the reaction is completed, then extract 3 times with 20 mL of benzene, combine the extracts, remove the solvent under reduced pressure to obtain a purple solid, recrystallize with absolute ethanol to obtain a white solid N - ethyl p-methylphenylglycine;

[0034] Step two: N - Preparation of p-methylphenyl-3-acetyl-4-hydroxypyrrolin-2-one:

[0035] Pick N - 1 g (1.3 mmol) of ethyl p-methylphenylglycine, 0.28 g (1.9 mmol) of ethyl acetoacetate, and 5 mL of dry xylene were added to a three-neck flask, refluxed at 125-130°C for 24 h, and then cooled...

Embodiment 2

[0039] Embodiment two, N - Preparation of p-tolyl-3-[3-(2-methoxyphenyl)-2-en-1-one]-4-hydroxypyrroline-2-one (compound number I2).

[0040] first step: N - Preparation of ethyl p-methylphenylglycine.

[0041] Add 0.55 g (5 mmol) of p-toluidine, 0.73 g (6 mmol) of ethyl chloroacetate, 10 mL of 95% ethanol, and 0.49 g (5 mmol) of sodium acetate into a 50 mL three-neck flask. Heat to reflux for 6 h, add 20 mL of water after the reaction is completed, then extract 3 times with 20 mL of benzene, combine the extracts, remove the solvent under reduced pressure to obtain a purple solid, recrystallize with absolute ethanol to obtain a white solid N - p-methylphenylglycine ethyl ester.

[0042] Step two: N - Preparation of p-methylphenyl-3-acetyl-4-hydroxypyrrolin-2-one.

[0043] Pick N - 1 g (1.3 mmol) of ethyl p-methylphenylglycine, 0.28 g (1.9 mmol) of ethyl acetoacetate, and 5 mL of dry xylene were added to a three-neck flask, refluxed at 125-130°C for 24 h, and then cooled t...

Embodiment 3

[0046] Embodiment three, N - Preparation of p-tolyl-3-[3-(2,6-dichlorophenyl)-2-en-1-one]-4-hydroxypyrrolin-2-one (compound number I13).

[0047] first step: N - Preparation of ethyl p-methylphenylglycine.

[0048] Add 0.55 g (5 mmol) of p-toluidine, 0.73 g (6 mmol) of ethyl chloroacetate, 10 mL of 95% ethanol, and 0.49 g (5 mmol) of sodium acetate into a 50 mL three-neck flask. Heat to reflux for 6 h, add 20 mL of water after the reaction is completed, then extract 3 times with 20 mL of benzene, combine the extracts, remove the solvent under reduced pressure to obtain a purple solid, recrystallize with absolute ethanol to obtain a white solid N - p-methylphenylglycine ethyl ester.

[0049] Step two: N - Preparation of p-methylphenyl-3-acetyl-4-hydroxypyrrolin-2-one.

[0050] Pick N - 1 g (1.3 mmol) of ethyl p-methylphenylglycine, 0.28 g (1.9 mmol) of ethyl acetoacetate, and 5 mL of dry xylene were added to a three-neck flask, refluxed at 125-130°C for 24 h, and then coo...

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Abstract

The invention discloses an N-substituent-3-[3-(substituted phenyl)-2-allyl-1- ketone]-4-hydroxypyrroline-2-ketone compound as well as a preparation method and application thereof, belonging to the technical field of organic synthesis and pesticides. The compound has a general structural formula (I). The N-substituent-3-[3-(substituent phenyl)-2-allyl-1- ketone]-4-hydroxypyrroline-2-ketone compound is synthesized from substituted phenylamine, ethyl chloroacetate, ethyl acetoacetate and substituted benzaldehyde. The compound has good tobacco mosaic virus resistant living body treatment activity and can be used for preparing plant virus resistant pesticides.

Description

technical field [0001] The present invention relates to compounds having anti-plant viruses and plant fungi, in particular N - Preparation method and application of substituted-3-[3-(substituted phenyl)-2-en-1-one]-4-hydroxypyrroline-2-one compounds. Background technique [0002] Pyrroline compounds are a class of important heterocyclic compounds, which have pesticide and pharmaceutical activities such as bactericidal, herbicidal, insecticidal, acaricidal, anti-tumor, and anti-infection. 1,4-Pentadien-3-one compound is a kind of curcumin analogue, which has anti-plant fungus, anti-plant virus, anti-cancer, anti-inflammatory, anti-oxidation, anti-HIV and other pesticide and pharmaceutical activities. Therefore, it has broad prospects for further development by introducing 1,4-pentadien-3-one structure with pyrroline compounds as the natural skeleton. [0003] In 1993, Addor et al. (Addor, R. W.; Donovan, S. F.; DIehl, R. E. N -Acylated A rylpyrroles Useful as In sectIcIdal...

Claims

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Application Information

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IPC IPC(8): C07D207/38A01P3/00A01P1/00
CPCA01N43/36C07D207/38
Inventor 杨松冉义江薛伟吴志兵陈玲张东阳丁永正刘斌胡德禹向红梅张腾腾
Owner GUIZHOU UNIV
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