Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesizing oxazole ring derivative by catalyzing beta, gamma-unsaturated oxime

A synthesis method and derivative technology, applied in the field of organic compound synthesis, can solve the problems of insufficient environmental protection and high cost, and achieve the effect of practical universal path, easy raw materials, and raw materials

Pending Publication Date: 2022-07-12
SUN YAT SEN UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In summary, although the current method of catalyzing β, γ-unsaturated oximes to synthesize oxazole ring derivatives has made some progress, there are still problems such as not being environmentally friendly and requiring the use of noble metal catalysts, resulting in high costs.

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
  • Method for synthesizing oxazole ring derivative by catalyzing beta, gamma-unsaturated oxime
  • Method for synthesizing oxazole ring derivative by catalyzing beta, gamma-unsaturated oxime
  • Method for synthesizing oxazole ring derivative by catalyzing beta, gamma-unsaturated oxime

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 Catalytic synthesis of β,γ-unsaturated oxime to 3-(3-methoxyphenyl)-5-methyl-4,5-dihydroisoxazole

[0041] The synthetic reaction formula is as follows:

[0042]

[0043] The specific synthesis method is as follows: 1-(3-methoxyphenyl)but-3-en-1-one oxime (compound 1, 38.2mg) and decacarbonyldimanganese (Mn 2 CO 10 , 7.8 mg) was placed in a 15 mL reaction tube, and after nitrogen was replaced three times, 2 mL of isopropanol (tBuOOH) was added as a solvent under nitrogen flow, followed by tert-butyl hydroperoxide (iPrOH, 36 mg), and the bottle was stoppered. The reaction temperature was raised to 100 °C, the solvent was removed after 4 hours of reaction, and the product compound (I) was obtained by column chromatography: 3-(3-methoxyphenyl)-5-methyl-4,5-di Hydroisoxazole (31 mg, 81% yield). The product is a white solid, NMR data ( figure 1 , 2 )for: 1 HNMR (400MHz, CDCl 3 )δ7.27(q,J=9.1,8.5Hz, 1 H),7.15(d,J=7.6Hz, 1 H),6.93(dd,J=8.3,2.6Hz, 1 H),4....

Embodiment 2

[0044] Example 2 Catalysis of β,γ-unsaturated oxime to synthesize 5-methyl-3-(4-trifluoromethyl)-4,5-dihydroisoxazole

[0045] The synthetic reaction formula is as follows:

[0046]

[0047] The specific synthesis method is as follows: 1-(4-trifluoromethyl)but-3-en-1-one oxime (compound 2, 45.8mg) and decacarbonyldimanganese (Mn 2 CO 10 , 7.8 mg) was placed in a 15 mL reaction tube, and after nitrogen was replaced three times, 2 mL of isopropanol (tBuOOH) was added as a solvent under nitrogen flow, followed by tert-butyl hydroperoxide (iPrOH, 36 mg), and the bottle was stoppered. The reaction temperature was raised to 100°C, the reaction was cooled to room temperature after 9 hours, the solvent was removed, and the product compound (II) was obtained by column chromatography: 5-methyl-3-(4-trifluoromethyl) -4,5-Dihydroisoxazole (34.3 mg, 75%), NMR data of the product ( image 3 , 4 )for: 1 H NMR (400MHz, CDCl 3 )δ7.77(d, J=8.1Hz, 1 H),7.65(d,J=8.3Hz, 1 H), 5.00–4.86 ...

Embodiment 3

[0048] Example 3 Catalysis of β,γ-unsaturated oxime to synthesize 3-(p-tolyl)-4,5-dihydroisoxazol-5-yl)-methanol

[0049] The synthetic reaction formula is as follows:

[0050]

[0051] The specific synthesis method is as follows: 1-(p-tolyl)but-3-en-1-one oxime (compound 3,35mg) and decacarbonyldimanganese (Mn 2 CO 10 , 7.8mg) was placed in a 10mL reaction tube, 2mL of trifluoroethanol (TFEA) was added as a solvent, and air was used as an oxidant at 25°C for 1.2 hours of reaction, and then triphenylphosphine (PPh) was added. 3 , 52.4 mg) reacted for 20 min, the solvent was removed and separated by column chromatography to obtain the product compound (III): 3-(p-tolyl)-4,5-dihydroisoxazol-5-yl)-methanol (28.7 mg , the yield is 82%). The product is a colorless liquid, NMR data ( Figure 5 , 6 )for: 1 H NMR (400MHz, CDCl 3 )δ7.54(d, J=7.9Hz, 1 H),7.30–7.13(m, 1 H),4.84(s, 0 H),3.85(dd,J=12.2,3.3Hz, 1 H),3.69(d,J=4.8Hz, 0 H),3.30(dd,J=24.5,9.2Hz, 1 H), 2.37(s, 1 ...

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 belongs to the technical field of synthesis of organic compounds, and relates to the technical field of synthesis of oxazole ring derivatives, in particular to a method for catalyzing beta, gamma-unsaturated oxime to synthesize oxazole ring derivatives. 5-methylated oxazole ring derivatives and 5-hydroxymethylated oxazole ring derivatives with high synthesis value and high biological activity are respectively synthesized from gamma, gamma-unsaturated oxime under different oxidants. The dimanganese decenecarbonyl used as the catalyst is a commercially available metal catalyst, is cheap and has good biological friendliness; according to the method, the oxidative cyclization reaction of the beta, gamma-unsaturated oxime substrate can be realized by using clean oxidants such as air or tert-butyl hydroperoxide under mild conditions, the reaction is more environment-friendly, and the commercial value is higher; different types of oxazole ring derivatives can be efficiently synthesized through the same catalytic system, and a more practical universal path is provided for synthesis of the oxazole ring derivatives.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, relates to the technical field of synthesis of oxazole ring derivatives, and particularly relates to a method for catalyzing β,γ-unsaturated oxime to synthesize oxazole ring derivatives. Background technique [0002] Oxazole ring is a kind of very important heterocyclic structure, which widely exists in various types of natural products, highly biologically active compounds and drugs, and its derivatives usually also have very efficient antibacterial, antiviral and other biological activities. Therefore, the development of a green, efficient and stable catalytic synthesis method for this type of structure is of great significance in both synthetic chemistry and medicinal chemistry. [0003] At present, some research progress has been made in the synthesis of oxazole ring derivatives, the most common of which is the synthesis of oxazole ring derivatives by catalyzing β,γ-unsatur...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/04
CPCC07D261/04Y02P20/584
Inventor 孟山水张宏侯克强陈新滋
Owner SUN YAT SEN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap 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