Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Preparation method of polysubstituted oxazole-2 (3H)-ketone compound

A ketone compound, multi-substitution technology, applied in the field of preparation of multi-substituted oxazol-2-one compounds, can solve problems such as limiting the scope of application

Active Publication Date: 2020-08-14
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of non-cyclic precursors to construct oxazol-2-one ring structures is mainly realized by the reaction of α-hydroxy ketones and isocyanates, but such reactions often require the introduction of catalysts such as tributyl phosphate, etc. It is carried out under high temperature, anhydrous and oxygen-free conditions, which limits its application range

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
  • Preparation method of polysubstituted oxazole-2 (3H)-ketone compound
  • Preparation method of polysubstituted oxazole-2 (3H)-ketone compound
  • Preparation method of polysubstituted oxazole-2 (3H)-ketone compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0034] The present invention provides a preparation method of multi-substituted oxazol-2(3H)-one compounds, comprising: reacting acrylamide compounds represented by formula (I) with hypervalent iodine reagents in the presence of auxiliary agents, Obtain the multi-substituted oxazol-2(3H)-one compound represented by formula (II);

[0035]

[0036] Among them, -R 1 ,-R 2 with -R 4 Each independently is -A, -Ar or -Het; -R 3 for-A;

[0037] The -A is C1-C30 chain alkyl, C1-C30 substituted chain alkyl or C3-C7 cycloalkyl, preferably C1-C20 chain alkyl, C1-C20 substituted chain Alkyl or C3-C7 cycloalkyl, more preferably C1-C10 chain alkyl, C1-C10 substituted chain alkyl or C3-C7 cycloalkyl, more preferably C1-C5 chain Alkyl, C1~C5 substituted chain alkyl or C3~C7 cycloalkyl, most preferably C1~C3 chain alkyl, C1~C3 substituted chain alkyl or C3~C7 cycloalkyl .

[0038] The number of substituents in the C1-C30 substituted chain alkyl group is preferably 1-20, more preferab...

Embodiment 1

[0056] Synthesis of 3-(4'-methylphenyl)-4-acetyl-5-methyl-oxazol-2(3H)-one

[0057] At room temperature, add 1.5mmol of PIFA, 1.0mmol of TFA and 40.0mL of dichloromethane into a 50mL round bottom flask and mix well, then add 1.0mmol of N-(4′-methylphenyl)- 2-Acetyl-3-methylamino-2-butenamide, react at room temperature for 0.5 hours. After the reaction, pour the reaction solution into 50.0 mL of saturated NaCl aqueous solution, then extract three times with 20.0 mL of dichloromethane, combine the organic phases, add 3.0 g of anhydrous sodium sulfate to dry, filter to remove the solid, and then remove the organic solvent , the residue was separated by silica gel column chromatography (petroleum ether / ethyl acetate=5:1) to obtain 3-(4'-methylphenyl)-4-acetyl-5-methyl-oxazole-2( 3H)-ketone, 65% yield, >99% purity.

[0058] The 3-(4′-methylphenyl)-4-acetyl group-5-methyl-oxazol-2(3H)-one obtained in Example 1 is analyzed by nuclear magnetic resonance spectrum, and its hydrogen nu...

Embodiment 2

[0062] Synthesis of 3-(4'-methylphenyl)-4-acetyl-5-methyl-oxazol-2(3H)-one

[0063] At room temperature, add 2.0mmol of PhIO, 3.0mmol of TFA and 20.0mL of 1,2-dichloroethane into a 50mL round bottom flask and mix well, then add 1.0mmol of N-(4′-formazan phenyl)-2-acetyl-3-methylamino-2-butenamide, reacted at room temperature for 4.0 hours. After the reaction, pour the reaction solution into 50.0 mL of saturated NaCl aqueous solution, then extract three times with 20.0 mL of dichloromethane, combine the organic phases, add 3.0 g of anhydrous sodium sulfate to dry, filter to remove the solid, and then remove the organic solvent , the residue was separated by silica gel column chromatography (petroleum ether / ethyl acetate=5:1) to obtain 3-(4'-methylphenyl)-4-acetyl-5-methyl-oxazole-2( 3H)-ketone, 55% yield, >99% purity.

[0064] The 3-(4′-methylphenyl)-4-acetyl-5-methyl-oxazol-2(3H)-one obtained in Example 2 was analyzed by nuclear magnetic resonance spectrum, which was the sam...

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

No PUM Login to View More

Abstract

The invention provides a synthesis method of a polysubstituted oxazole-2 (3H)-ketone compound, and the method comprises the following steps: using an acrylamide compound represented by formula (I) asa raw material, reacting the acrylamide compound with a high-valence iodine reagent in the presence of an assistant to obtain the polysubstituted oxazole-2 (3H)-ketone compound represented by formula(II). Compared with the synthesis method of the polysubstituted oxazolidinone compound in the prior art, the synthesis method has the advantage that the polysubstituted oxazole-2 (3H)-ketone compoundis synthesized by utilizing the cyclization reaction of the acrylamide compound in which the high-valence iodine reagent participates. The synthesis method has the advantages of easily available raw materials, simple operation and mild reaction conditions, and R1, R2, R3 and R4 can be a plurality of different substituents, so the synthesis method has a wide application range.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of polysubstituted oxazol-2(3H)-one compounds. Background technique [0002] Oxazolidinone compounds are one of the most popular heterocyclic compounds researched at home and abroad. This type of compound has been widely used in the synthesis and functional modification of polymer materials, and also plays an important role in the fields of organic synthesis and biomedicine. application value. As synthetic precursors, oxazolidinone compounds can be used to prepare a series of new chiral amino acids through metal-catalyzed asymmetric synthesis; as catalyst ligands, oxazolidinone compounds can be used in small organic molecule synthesis reactions and polymerization reactions middle. Moreover, many compounds containing the core structure of oxazolidinone have good biological and pharmaceutical activities, and can be used in antibacterial,...

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): C07D263/38
CPCC07D263/38
Inventor 董德文李柏傧张睿王钰胡佳娜
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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
Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com