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Method for synthesizing ortho-aldehyde group-containing alpha-ketoamide compound

A synthesis method and ketoamide technology are applied in the preparation of organic compounds, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc. Expensive, increase synthesis cost and other problems, to achieve the effect of wide application range of substrate, cheap dosage, increase synthesis cost

Active Publication Date: 2019-05-21
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses raw materials with halogen atoms, which is not conducive to environmental protection, and the anthranilaldehyde is expensive, which greatly increases the synthesis cost

Method used

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  • Method for synthesizing ortho-aldehyde group-containing alpha-ketoamide compound
  • Method for synthesizing ortho-aldehyde group-containing alpha-ketoamide compound
  • Method for synthesizing ortho-aldehyde group-containing alpha-ketoamide compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The structural formula of the ortho aldehyde group α-ketoamide compound prepared in this embodiment is as follows:

[0033]

[0034] The preparation method is: 0.3mmol 5-methoxybenzo[c]isoxazole (44.7mg), 0.6mmol benzoylformic acid (90.1mg), 0.015mmol copper bromide (3.3mg) and 0.06mmol triphenyl Phosphine (15.7 mg) was added to a 25 ml schlenk tube, and the reaction tube was replaced with argon three times under reduced pressure. 1,2-Dichloroethane (3 ml) was added, and stirred at 110° C. for 12 hours. After the reaction is completed, add 100-200 mesh column chromatography silica gel, and distill the solvent under reduced pressure. Elution, by means of TLC elution tracking detection, collect the eluate containing the target product, combine the eluate of the target product, evaporate and concentrate to obtain the α-ketoamide compound of the ortho aldehyde group shown in formula III. The material was a yellow solid, 72% yield.

[0035] Characterization data: m.p.1...

Embodiment 2

[0037] The structural formula of the ortho aldehyde group α-ketoamide compound prepared in this embodiment is as follows:

[0038]

[0039] The preparation method is: 0.3mmol 5-fluorobenzo [c] isoxazole (41.1mg), 0.6mmol benzoylformic acid (90.1mg), 0.015mmol CuBr (PPh 3 ) 3(13.9 mg) was added to a 25 ml schlenk tube, and the reaction tube was replaced with argon three times under reduced pressure. 1,2-Dichloroethane (3 ml) was added, and stirred at 110° C. for 12 hours. After the reaction is completed, add 100-200 mesh silica gel for column chromatography, and distill the solvent under reduced pressure. Elution, by means of TLC elution tracking detection, collect the eluate containing the target product, combine the eluate of the target product, evaporate and concentrate to obtain the α-ketoamide compound of the ortho aldehyde group shown in formula III. The material was a yellow solid in 70% yield.

[0040] Characterization data: m.p.133-135℃; 1 H NMR (400MHz, CDCl ...

Embodiment 3

[0042] The structural formula of the ortho aldehyde group α-ketoamide compound prepared in this embodiment is as follows:

[0043]

[0044] The preparation method is:

[0045] 0.3 mmol 5-chlorobenzo[c]isoxazole (46 mg), 0.6 mmol benzoylformic acid (90.1 mg), 0.015 mmol copper bromide (3.3 mg) and 0.06 mmol triphenylphosphine (15.7 mg) were added Into a 25 ml schlenk tube, the reaction tube was replaced with argon three times under reduced pressure. 1,2-Dichloroethane (3 ml) was added, and stirred at 110° C. for 12 hours. After the reaction is completed, add 100-200 mesh silica gel for column chromatography, and distill the solvent under reduced pressure. Elution, by means of TLC elution tracking detection, collect the eluate containing the target product, combine the eluate of the target product, evaporate and concentrate to obtain the α-ketoamide compound of the ortho aldehyde group shown in formula III. The material was a yellow solid in 75% yield.

[0046] Characteri...

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Abstract

The invention discloses a method for synthesizing an ortho-aldehyde group-containing alpha-ketoamide compound. Benzo[c]isoxazole shown in formula I and benzoyl formic acid shown in formula II are dissolved in an organic solvent and react in an inert atmosphere under the function of a catalyst, and an obtained reaction liquid is purified to obtain the ortho-aldehyde group-containing alpha-ketoamidecompound shown in formula III. The method has the advantages that the adopted raw materials are low in cost, the method is environmentally friendly, the use quantity of the catalyst is small, the catalytic efficiency is high, and the application range of substrates is wide. The formulas are show in the description.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing α-ketoamide compounds with ortho aldehyde groups. technical background [0002] The α-ketoamide with ortho aldehyde group is the core skeleton structure of bioactive substances, synthetic drugs and natural medicines, and has a wide range of applications in biological and pharmacological research. In addition, the α-ketoamide moiety of the ortho aldehyde group widely exists in fungicides, fungicide precursors and various inhibitors, and is also a key intermediate for the synthesis of some important compounds. [0003] The only existing method (Z.Naturforsch B, 1995, 50, 326-332) for synthesizing α-ketoamides with ortho aldehyde groups is to condense benzoyl chloride and anthranilaldehyde. This method uses raw materials with halogen atoms, which is more polluting and unfavorable for environmental protection, and anthranilaldehyde is expensive,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/24C07C231/10C07C235/78B01J31/24
Inventor 邹亮华朱昊朱帅李平贵闫成范敏
Owner JIANGNAN UNIV
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