Preparation method of 3-aryl-2H-benzo [beta] [1, 4] benzoxazine-2-ketone compound

A technology of benzoxazine and ketone compounds, which is applied in the field of organic synthesis, can solve problems such as limitations and insufficient environmental protection of catalysts, and achieve the effects of environmentally friendly reaction conditions, cheap synthesis methods, and few by-products

Active Publication Date: 2020-05-05
EAST CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, the catalysts used in the above two methods are not environmentally friendly, and the scope of substrates is limited, so it is of positive significance to develop a green preparation method with a wider application range

Method used

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  • Preparation method of 3-aryl-2H-benzo [beta] [1, 4] benzoxazine-2-ketone compound
  • Preparation method of 3-aryl-2H-benzo [beta] [1, 4] benzoxazine-2-ketone compound
  • Preparation method of 3-aryl-2H-benzo [beta] [1, 4] benzoxazine-2-ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] A preparation method of a 3-aryl-2H-benzo[β][1,4]benzoxazin-2-one compound, the synthesis route of which is as follows:

[0030]

[0031] Specifically include the following steps:

[0032] (1) Take a 10mL reaction bottle, add 0.2mmol 2-aminophenol, 0.4mmol benzoylformic acid and 2mL deep eutectic solvent (the molar ratio of choline chloride to urea is 1:2);

[0033] (2) Put the reaction bottle in step (1) into an 80°C oil bath for magnetic stirring, and react for 2 hours to obtain the crude product;

[0034] (3) The crude product obtained in step (2) is separated by column chromatography, the eluent is a mixture of ethyl acetate and petroleum ether, the volume ratio is 1:6, and dried at 30°C for 3 hours to obtain 3-aryl -2H-Benzo[β][1,4]benzoxazin-2-one compound.

[0035] The obtained target product is carried out the mensuration of proton nuclear magnetic resonance spectrum:

[0036] 1 H NMR (500MHz, DMSO) δ8.19 (d, J = 6.9Hz, 2H), 7.84 (d, J = 6.8Hz, 1H), 7.63–...

Embodiment 2

[0038]

[0039] A preparation method of a 3-aryl-2H-benzo[β][1,4]benzoxazin-2-one compound specifically comprises the following steps:

[0040] (1) Take a 10mL reaction bottle, add 0.2mmol 4-chloro-2-aminophenol, 0.4mmol benzoylformic acid and 2mL deep eutectic solvent (the molar ratio of choline chloride to urea is 1:2);

[0041] (2) Put the reaction bottle in step (1) into an 80°C oil bath for magnetic stirring, and react for 2 hours to obtain the crude product;

[0042] (3) The crude product obtained in step (2) is separated by column chromatography, the eluent is a mixture of ethyl acetate and petroleum ether, the volume ratio is 1:6, and dried at 30°C for 3 hours to obtain 3-aryl -2H-Benzo[β][1,4]benzoxazin-2-one compound.

[0043] The obtained target product is carried out the mensuration of proton nuclear magnetic resonance spectrum:

[0044] 1 H NMR (500MHz, DMSO) δ8.19 (d, J = 7.2Hz, 2H), 7.91 (d, J = 2.4Hz, 1H), 7.64 (dd, J = 8.8, 2.4Hz, 1H), 7.61–7.47 (m,4H)....

Embodiment 3

[0046]

[0047] A preparation method of 3-aryl-2H-benzo[β][1,4]benzoxazin-2-one compound, specifically comprising the following steps:

[0048] (1) Take a 10mL reaction bottle, add 0.2mmol 5-methyl-2-aminophenol, 0.4mmol benzoylformic acid and 2mL deep eutectic solvent (the molar ratio of choline chloride to urea is 1:2);

[0049] (2) Put the reaction bottle in step (1) into an 80°C oil bath for magnetic stirring, and react for 2 hours to obtain the crude product;

[0050](3) The crude product obtained in step (2) is separated by column chromatography, the eluent is a mixture of ethyl acetate and petroleum ether, the volume ratio is 1:6, and dried at 30°C for 3 hours to obtain 3-aryl -2H-Benzo[β][1,4]benzoxazin-2-one compound.

[0051] The target product that makes is carried out the mensuration of nuclear magnetic resonance spectrum and carbon spectrum:

[0052] 1 H NMR (500MHz, CDCl3) δ8.31(d, J=2.9Hz, 2H), 7.71(d, J=8.1Hz, 1H), 7.49(dd, J=12.8, 5.3Hz, 3H), 7.19(d , J...

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Abstract

The invention discloses a preparation method of a 3-aryl-2H-benzo [beta] [1, 4] benzoxazine-2-ketone compound, which comprises the following steps: carrying out magnetic stirring on a reaction substrate 2-aminophenol compound and a ketonic acid compound in an oil bath pot by using a deep eutectic solvent as a reaction solvent, and carrying out after-treatment after the reaction is finished, thereby obtaining the 3-aryl-2H-benzo [beta] [1, 4] benzoxazine-2-ketone compound. The deep eutectic solvent is formed by uniformly mixing choline chloride and urea according to a molar ratio of 1: 2, and then heating the mixed solution to a uniform and transparent liquid at 80 DEG C. The method is simple in operation process, mild in reaction condition, low in cost and environmentally friendly, and hasapplication and popularization value.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of a 3-aryl-2H-benzo[β][1,4]benzoxazin-2-one compound. Background technique [0002] 3-Aryl-2H-benzo[β][1,4]benzoxazin-2-ones are organic heterocyclic compounds with photophysical and photochemical activities, antibacterial activities and antitumor activities. As their potential applications in materials and medicinal chemistry are becoming more and more important, it is very attractive to develop efficient and green methodologies to obtain benzoxazine derivatives. [0003] At present, the preparation method of benzoxazine compound has following several synthetic methods: [0004] 3-aryl-2H-benzo[β][1,4]benzoxazin-2-one was synthesized by using 2-aminophenol and ketoacid as reaction substrate; [0005] Synthesis of 3-aryl-2H-benzo[β][1,4]benzoxazin-2-ones by reaction of benzoxazole ring-opening and ketoacids; [0006] However, the catalysts used in the abo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/36
CPCC07D265/36
Inventor 姜国芳陈国庆谢宗波乐长高祝志强陈中胜
Owner EAST CHINA UNIV OF TECH
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