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4-phenyl-6H-1,3-oxazine-6-one derivative, preparation and application thereof

A technology of -6H-1, derivatives, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve the problems of large substrate limitations, cumbersome product post-processing, and unfriendly environment.

Active Publication Date: 2020-11-06
SUZHOU UNIV
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  • 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

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  • 4-phenyl-6H-1,3-oxazine-6-one derivative, preparation and application thereof
  • 4-phenyl-6H-1,3-oxazine-6-one derivative, preparation and application thereof
  • 4-phenyl-6H-1,3-oxazine-6-one derivative, preparation and application thereof

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 4-methyl-3-phenylisoxazol-5(4H)-one (compound corresponding to numbering (1), 0.0350g), 0.02mmol palladium dichloride (0.0036g), 0.04mmol sodium benzoate (0.0058g), in a 10mL test tube reaction tube, add 2mL of 1,1,2-trichloroethane as a solvent, and finally add tert-butylisonitrile (compound corresponding to number (17), 45 microliters) with a rubber stopper for the test tube mouth Sealed, stirred and reacted for 6 hours at 85°C; after the reaction, the reaction solution was concentrated in vacuum and separated by column chromatography (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), mobile phase change program (A:B) is 1:10), to obtain 0.0438g reaction product.

[0053] The above-mentioned reaction product is characterized, and the result is:

[0054] ...

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 (compound corresponding to No. (2), 0.0378g), 0.02mmol palladium dichloride (0.0036g), 0.04mmol sodium benzoate (0.0058 g) In a 10mL test tube reaction tube, add 2mL 1,1,2-trichloroethane as a solvent, and finally add tert-butylisonitrile (compound corresponding to number (17), 45 microliters) and seal the test tube mouth with a rubber stopper , stirring and reacting at 85°C for 6 hours; after the reaction, the reaction solution was concentrated in vacuum and separated by column chromatography (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) is 1:10), and 0.0533g of the reaction product was obtained.

[0058] The above-mentioned reaction product is characterized, and the result is:

[0059] 1...

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 (compound corresponding to number (3), 0.0410g), 0.02mmol palladium dichloride (0.0036g) , 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 tert-butylisonitrile (compound corresponding to number (17), 45 microliters ) The test tube mouth was closed with a rubber stopper, and stirred and reacted at 85°C for 6 hours; Ethyl acetate (A) and petroleum ether (B), the mobile phase change program (A:B) is 1:10), and 0.0484g of the reaction product was obtained.

[0063] The above-mentioned reaction product is characterized, and the result is:

[0064] 1 H NMR (400MHz, Chloroform-d) δ7.66–7.37(m,2H),7.04–6.82(m,2H),5.27(s,1H),3.84(s,3H),2.07(s,3H), 1.43(s,9H)ppm; according to the characterization data, the obtained reaction product is 2-(tert-butylamino)-5-m...

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Abstract

The invention relates to a 4-phenyl-6H-1,3-oxazine-6-one derivative, a preparation method and application thereof, and provides a class of 4-phenyl-6H-1,3-oxazine-6-one derivatives represented by a formula (III). According to the invention, the preparation method is mild in condition, simple and safe to operate and relatively high in yield, and the 4-phenyl-6H-1,3-oxazine-6-one derivative obtainedby the invention has aggregation-induced emission (AIE) characteristics and can be applied to the photoelectric field.

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 a certain tumor suppressor effect in related research (J.Am.Chem.Soc., 2013,135,13387-1339.); while research on Cetilistat ATL-962 shows 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., 1978,20,902-903....

Claims

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Application Information

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Patent Type & Authority Applications(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
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