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
View PDF6 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But 1,3,4-oxadiazole sulf

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 4-hydroxyl pyrroline-2-ketone derivative containing 1,3,4-oxadiazole and preparation method and application of 4-hydroxyl pyrroline-2-ketone derivative
  • 4-hydroxyl pyrroline-2-ketone derivative containing 1,3,4-oxadiazole and preparation method and application of 4-hydroxyl pyrroline-2-ketone derivative
  • 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

Example Embodiment

[0027] Example 1: 3-(5-(phenyl)-1,3,4-oxadiazol-2-sulfanyl)-1-(4-methylphenyl)-4-hydroxy-pyrrolidin-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, and add 1 mL (20.1 mmol) of concentrated sulfuric acid dropwise, heat to reflux for 2 h, TLC detects the end of the reaction, and adjust the pH with saturated sodium carbonate solution To about 7, extract with dichloromethane (30mL×3), combine the organic phases, dry with anhydrous sodium sulfate, desolvate, and column chromatography (PE:EA=10:1, V / V ) 2.2 g of colorless oily liquid was obtained, and the yield was 89.4%;

[0030] (2) Preparation of benzoyl hydrazide

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

Example Embodiment

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

[0044] (1) Preparation of ethyl benzoate

[0045] Synthesis as in Example 1 (1) method and conditions,

[0046] (2) Preparation of benzoyl hydrazide

[0047] Synthesize as in Example 1 (2) method and conditions.

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

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

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

[0051] It was synthesized according to the method and conditions of Example 1 (4), replacing (18.66 mmol) 4-methylaniline with (21.48 mmol) aniline.

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

[0053] Synthesize as in Example 1 (5) method and conditions, (15.52 mmol) N -(P-tolyl)glycine ethyl ester is replaced by (16.76 mmol) N -(P-tolyl)glycine ethyl ester

[0054] (6) N -(2-Bromoacetyl)- N -Phenyl-(2-(5-phenyl-1,3,4-oxadiazole-2-mercapto)acetyl) glycine ethyl ester

[0055] Sy...

Example Embodiment

[0058] Example 3: 3-(5-(4-Fluorophenyl)-1,3,4-oxadiazol-2-sulfanyl)-1-(4-chlorophenyl)-4-hydroxy-pyrroline- 2 Ketone (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 with (14.27 mmol) 4-fluorobenzoic acid

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

[0062] It was synthesized as in Example 1 (2) method and conditions, except that (13.32 mmol) ethyl benzoate was replaced with (11.89 mmol) ethyl 4-fluorobenzoate.

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

[0064] It was synthesized as in Example 1 (3) method and conditions, except that (11.02 mmol) benzoyl hydrazide was replaced with (9.73 mmol) p-fluorobenzoyl hydrazide.

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

[0066] It was synthesized according to the method and conditions of Example 1 (4), except that (18.66 mmol) 4-methylaniline was added to...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap