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

4-Phenyl-6h-1,3-oxazin-6-one derivatives and their preparation and application

A derivative, phenyl technology, applied in 4-phenyl-6H-1,3-oxazin-6-one derivatives and their preparation and application fields, can solve the problems of cumbersome post-processing, unfriendly environment, bottom It can solve the problems of large limitations and other problems, and achieve the effects of wide substrate universality, high atom utilization, simple and mild reaction conditions.

Active Publication Date: 2022-07-19
SUZHOU UNIV
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are some disadvantages in the method of synthesizing 1,3-oxazin-6-ones by isoxazolones: 1) need to use highly toxic POCl 3 (Phosphorus oxychloride), unfriendly to the environment, and the post-treatment of the product is loaded down with trivial details; 2) need to use some explosive dangerous reagents such as diazonium compounds etc.; 3) substrate limitation is bigger, some methods are only applicable to alkyl iso Oxazolone, and the yield is only moderate

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-Phenyl-6h-1,3-oxazin-6-one derivatives and their preparation and application
  • 4-Phenyl-6h-1,3-oxazin-6-one derivatives and their preparation and application
  • 4-Phenyl-6h-1,3-oxazin-6-one derivatives and their preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Synthesis of 2-(tert-butylamino)-5-methyl-4-phenyl-6H-1,3-oxazin-6-one

[0052] Weigh 0.2mmol of 4-methyl-3-phenylisoxazol-5(4H)-one (the compound corresponding to No. (1), 0.0350g), 0.02mmol of palladium dichloride (0.0036g), 0.04mmol of sodium benzoate (0.0058g), in a 10mL test tube reaction tube, add 2mL 1,1,2-trichloroethane as a solvent, and finally add tert-butylisonitrile (the compound corresponding to No. (17), 45μL) with a rubber stopper for the test tube mouth Sealed, stirred and reacted at 85 ° C for 6 hours; after the reaction was completed, the reaction solution was successively subjected to vacuum concentration and column chromatography separation (column chromatography separation conditions: the stationary phase was 200~300 mesh silica gel powder, and the mobile phase was ethyl acetate (A ) and petroleum ether (B), the mobile phase change program (A:B) was 1:10) to obtain 0.0438 g of the reaction product.

[0053] The above reaction products were charact...

Embodiment 2

[0056] Synthesis of 2-(tert-butylamino)-5-methyl-4-(p-tolyl)-6H-1,3-oxazin-6-one

[0057] 4-Methyl-3-p-tolylisoxazol-5(4H)-one (the compound corresponding to No. (2), 0.0378g), 0.02mmol palladium dichloride (0.0036g), 0.04mmol sodium benzoate (0.0058g) g), in a 10 mL test tube reaction tube, add 2 mL of 1,1,2-trichloroethane as a solvent, and finally add tert-butyl isonitrile (the compound corresponding to No. (17), 45 microliters), and seal the mouth of the test tube with a rubber stopper , the reaction was stirred at 85°C for 6 hours; after the reaction, the reaction solution was successively subjected to vacuum concentration and column chromatography separation (column chromatography separation conditions: the stationary phase was 200-300 mesh silica gel powder, and the mobile phase was ethyl acetate (A) and petroleum ether (B), the mobile phase change program (A:B) was 1:10) to obtain 0.0533 g of the reaction product.

[0058] The above reaction products were characterize...

Embodiment 3

[0061] Synthesis of 2-(tert-butylamino)-5-methyl-4-(p-methoxyphenyl)-6H-1,3-oxazin-6-one

[0062] 3-(4-Methoxyphenyl)-4-methyl-isoxazol-5(4H)-one (the compound corresponding to No. (3), 0.0410 g), 0.02 mmol palladium dichloride (0.0036 g) , 0.04mmol sodium benzoate (0.0058g), in a 10mL test tube reaction tube, add 2mL 1,1,2-trichloroethane as a solvent, and finally add the compound corresponding to tert-butylisonitrile (No. (17), 45 μL ) The mouth of the test tube was closed with a rubber stopper, and the reaction was stirred at 85°C for 6 hours; after the reaction was completed, the reaction solution was successively subjected to vacuum concentration and column chromatography separation (column chromatography separation conditions: the stationary phase was 200-300 mesh silica gel powder, and the mobile phase was It was ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A:B) was 1:10) to obtain 0.0484 g of the reaction product.

[0063] The above ...

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 present invention relates to a 4-phenyl-6H-1,3-oxazine-6-one derivative and its preparation and application. The present invention provides a class of 4-phenyl-6H-1,3-oxazine-6-one derivatives as shown in formula (III), the preparation method has mild conditions, simple and safe operation, high yield, and The 4-phenyl-6H-1,3-oxazine-6-one derivatives obtained in the present invention have aggregation-induced emission (AIE) properties and can be applied to the field of optoelectronics.

Description

technical field [0001] The invention relates to the field of organic compounds, in particular to a 4-phenyl-6H-1,3-oxazin-6-one derivative and its preparation and application. Background technique [0002] As a special heterocyclic skeleton, 1,3-oxazin-6-one is widely distributed in natural products and drug molecules. For example, Discoipyrroles alkaloids have shown certain tumor suppressor effects in related studies (J.Am.Chem.Soc., 2013, 135, 13387-1339.); while studies on Cetilistat ATL-962 have shown that it can Effective inhibition of pancreatic lipase activity can be used as an anti-obesity drug (HormMetab Res, 2008, 40, 539-543.). The recently discovered alkaloids Spinoxazine A and B have also been shown to have an oxazinone skeleton (Org. Lett., 2015, 17, 5024-5027.; J. Nat. Prod., 2016, 79, 455-462.). In addition, 1,3-oxazin-6-one derivatives can also be used as intermediates in organic synthesis for further transformation (J.Chem.Soc., Chem.Commun., 1978, 20, 90...

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 Patents(China)
IPC IPC(8): C07D265/06C07D413/04C07D265/12C09K11/06
CPCC07D265/06C07D413/04C07D265/12C09K11/06C09K2211/1033C09K2211/1088C09K2211/1092C09K2211/1029
Inventor 纪顺俊祝一鸣汪顺义徐小平
Owner SUZHOU 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