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4-hydroxyl pyrroline-2-ketone derivative containing 1,3,4-oxadiazole and preparation method and application of 4-hydroxyl pyrroline-2-ketone derivative

A technology of hydroxypyrroline and oxadiazole, which is applied in the field of chemistry and technology, can solve problems such as compound instability, and achieve good inhibitory activity and stable compound effects

Active Publication Date: 2016-09-21
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But 1,3,4-oxadiazole sulfone compounds are unstable

Method used

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  • 4-hydroxyl pyrroline-2-ketone derivative containing 1,3,4-oxadiazole and preparation method and application of 4-hydroxyl pyrroline-2-ketone derivative
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  • 4-hydroxyl pyrroline-2-ketone derivative containing 1,3,4-oxadiazole and preparation method and application of 4-hydroxyl pyrroline-2-ketone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: 3-(5-(phenyl)-1,3,4-oxadiazol-2-sulfanyl)-1-(4-methylphenyl)-4-hydroxy-pyrroline-2-one (A-1), including the following steps:

[0028] (1) Preparation of ethyl benzoate

[0029] Add 2.0 g (16.38 mmol) of benzoic acid to a 100 mL round bottom flask, add 50 mL of ethanol to dissolve, add 1 mL (20.1 mmol) of concentrated sulfuric acid dropwise, heat and reflux for 2 h, TLC detects that the reaction is complete, and adjust the pH with saturated sodium carbonate solution to about 7, extracted with dichloromethane (30mL×3), combined the organic phases, dried over anhydrous sodium sulfate, precipitated, and column chromatography (PE:EA=10:1, V / V ) to obtain 2.2 g of colorless oily liquid, yield 89.4%;

[0030] (2) Preparation of Benzohydrazide

[0031] Add 2 g (13.32 mmol) of ethyl benzoate to a 100 mL round bottom flask, 50 mL of absolute ethanol as a solvent, add 1.00 g (19.98 mmol) of 80% hydrazine hydrate, and place the system in an oil bath at a temperature ...

Embodiment 2

[0043] Example 2: 3-(5-(phenyl)-1,3,4-oxadiazol-2-sulfanyl)-1-phenyl-4-hydroxy-pyrroline-2-one (A-2)

[0044] (1) Preparation of ethyl benzoate

[0045] As embodiment 1 (1) method and condition synthesis,

[0046] (2) Preparation of Benzohydrazide

[0047] Synthesize as embodiment 1 (2) method and condition.

[0048] (3) Preparation of 5-(phenyl)-1,3,4-oxadiazole-2-thiol

[0049] Synthesized as in Example 1 (3) method and conditions.

[0050] (4) N Preparation of -(4-phenyl)-glycine ethyl ester

[0051] Synthesized as in Example 1 (4) method and conditions, replacing (18.66 mmol) 4-methylaniline with (21.48 mmol) aniline.

[0052] (5) N -(2-Bromoacetyl)- N -(Phenyl)glycine ethyl ester

[0053] Synthesize as embodiment 1 (5) method and condition, (15.52 mmol) N -(p-tolyl)glycine ethyl ester was changed to (16.76 mmol) N -(p-Clyl)glycine ethyl ester

[0054] (6) N -(2-Bromoacetyl)- N Preparation of -phenyl-(2-(5-phenyl-1,3,4-oxadiazole-2-mercapto)acetyl)glycine eth...

Embodiment 3

[0058] Example 3: 3-(5-(4-fluorophenyl)-1,3,4-oxadiazole-2-thio)-1-(4-chlorophenyl)-4-hydroxy-pyrroline- 2 Ketones (A-4)

[0059] (1) Preparation of ethyl 4-fluorobenzoate

[0060] Synthesize as in Example 1 (1) method and conditions, the difference is that (16.38 mmol) benzoic acid is replaced by (14.27 mmol) 4-fluorobenzoic acid

[0061] (2) Preparation of 4-fluorobenzoic hydrazide

[0062] Synthesize as in Example 1 (2) method and conditions, the difference is that (13.32 mmol) ethyl benzoate is replaced with (11.89 mmol) 4-fluoroethyl benzoate.

[0063] (3) Preparation of 5-(4-fluorophenyl)-1,3,4-oxadiazole-2-thiol

[0064] Synthesize as in Example 1 (3) method and conditions, the difference is that (11.02 mmol) benzoyl hydrazide is replaced by (9.73 mmol) p-fluorobenzoic hydrazide.

[0065] (4) N Preparation of -(4-chlorophenyl)-glycine ethyl ester

[0066] Synthesize as in Example 1 (4) method and conditions, the difference is that adding (18.66 mmol) 4-methylanili...

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Abstract

The invention discloses a 4-hydroxyl pyrroline-2-ketone derivative containing 1,3,4-oxadiazole and a preparation method and application of the 4-hydroxyl pyrroline-2-ketone derivative. The structural general formula (I) is shown in the description, wherein in the formula (I), R1 is substitute arene and substitute benzyl, and R2 is substitute arene and hydrogen. The 4-hydroxyl pyrroline-2-ketone derivative has good bacterium and plant virus resisting activity, and is stable.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a 4-hydroxypyrrolin-2-one derivative containing 1,3,4-oxadiazole, and also to the 1,3,4-oxadiazole-containing Preparation method of 4-hydroxypyrroline-2-one derivatives and application of the 4-hydroxypyrroline-2-one derivatives containing 1,3,4-oxadiazole in anti-plant bacteria and anti-plant viruses . Background technique [0002] 4-Hydroxypyrroline-2-one compounds are natural product analogs, which have a wide range of pesticide and pharmaceutical biological activities such as bactericidal, herbicidal, insecticidal, anti-tumor, and anti-viral, which has aroused extensive interest of researchers and deepened their research. Many new drugs with biological activity have been obtained from the research. These compounds have variable structures but all contain a common structural unit five-membered lactam ring. Compounds with 1,3,4-oxadiazole structure are an importan...

Claims

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Application Information

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IPC IPC(8): C07D413/12A01N43/824A01P1/00
CPCA01N43/82C07D413/12
Inventor 杨松陈玲吴志兵王培义胡德禹薛伟李振兴周磊
Owner GUIZHOU UNIV
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