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Method for synthesizing quinazolinone compound through visible light induction

A quinazolinone and compound technology, which is applied in the field of visible light-induced synthesis of quinazolinone compounds, can solve the problems of cumbersome separation and purification steps, product metal residues, etc., and achieve wide substrate adaptability, high reaction efficiency, and mild reaction conditions Effect

Pending Publication Date: 2021-11-26
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods often require harsh reaction conditions. In addition, the addition of strong oxidants (such as potassium persulfate) and metal catalysts (such as palladium acetate, copper oxide) etc. leads to the presence of metal residues in the product, requiring cumbersome separation and purification steps
The recently developed photochemical reaction uses light as an energy source, which is more environmentally friendly than the traditional heating reaction. However, the photochemical reactions reported so far still require the addition of photocatalysts to achieve the desired reaction effect, and the disadvantages of using additives cannot be avoided.

Method used

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  • Method for synthesizing quinazolinone compound through visible light induction
  • Method for synthesizing quinazolinone compound through visible light induction
  • Method for synthesizing quinazolinone compound through visible light induction

Examples

Experimental program
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Effect test

Embodiment 1

[0037] A method for visible light-induced synthesis of the following quinazolinone compounds, the specific steps are as follows:

[0038]

[0039] Add 2-amino-N-methylbenzamide (0.2mmol), p-tolualdehyde (0.22mmol), 2mL glacial acetic acid in the 10mL reaction bottle, stir well, the gained reaction solution is in the purple light LED lamp of 5W (purple light Wavelength 390 ~ 400nm) irradiation, stirring reaction at room temperature for 16 hours, application of TLC to detect the completion of the reaction, add 10mL of distilled water to the reaction solution, stir at room temperature for 10 minutes, filter, wash the obtained solid with water three times, each 3mL, and then in 40 ℃ Vacuum drying for 6 hours gave a white solid which was the target product with a yield of 78%.

[0040] The hydrogen spectrogram and the carbon spectrogram of the obtained product are respectively as follows figure 1 and figure 2 As shown, nuclear magnetic resonance shows no impurities, and the p...

Embodiment 2

[0042] A method for visible light-induced synthesis of the following quinazolinone compounds, the specific steps are as follows:

[0043]

[0044] Add 2-aminobenzamide (0.2mmol), p-tolualdehyde (0.22mmol), and 2mL glacial acetic acid into a 10mL reaction bottle, stir well, and the resulting reaction solution is irradiated by a 5W purple LED lamp and stirred at room temperature for reaction After 16 hours, use TLC to detect that the reaction is complete, add 10 mL of distilled water to the reaction solution, stir at room temperature for 10 minutes, filter, wash the obtained solid with water three times, 3 mL each time, and then vacuum-dry at 40 ° C for 6 hours to obtain a white solid that is the target product , yield 78%.

[0045] The hydrogen spectrogram and the carbon spectrogram of the obtained product are respectively as follows image 3 and Figure 4 As shown, the structural characterization data are as follows:

[0046] 1 H NMR (500MHz, DMSO-d 6 )δ12.47(s,1H),8.1...

Embodiment 3

[0054]A method for visible light-induced synthesis of the following quinazolinone compounds, the specific steps are as follows:

[0055]

[0056] Add 2-aminobenzamide (0.2mmol), p-hydroxybenzaldehyde (0.22mmol), 2mL glacial acetic acid in a 10mL reaction flask, stir well, and the resulting reaction solution is irradiated by a 5W purple LED lamp and stirred at room temperature for 16 hour, after using TLC to detect that the reaction is complete, add 10 mL of distilled water to the reaction solution, stir at room temperature for 10 minutes, filter, wash the resulting solid with water three times, 3 mL each time, and then vacuum-dry at 40 ° C for 6 hours to obtain a white solid that is the target product. Yield 85%.

[0057] The hydrogen spectrogram and the carbon spectrogram of the obtained product are respectively as follows Figure 5 and Image 6 As shown, the structural characterization data are as follows:

[0058] 1 H NMR (500MHz, DMSO-d 6 )δ12.29(s,1H),10.14(s,1H),...

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Abstract

The invention provides a method for synthesizing a quinazolinone compound through visible light induction. By taking an anthranilamide compound (I) and an aldehyde compound (II) as raw materials, and taking glacial acetic acid as a solvent, reaction is performed under the irradiation of purple light to obtain the quinazolinone compound (III). The method for synthesizing the quinazolinone compound through visible light induction is mild in reaction condition, simple and convenient in post-treatment operation, free of additional additives, efficient in reaction, wide in substrate adaptability, high in product purity, green and environmentally friendly.

Description

technical field [0001] The invention belongs to the technical field of synthesis, and in particular relates to a method for synthesizing quinazolinone compounds induced by visible light. Background technique [0002] Quinazolinones are an important class of nitrogen-containing heterocyclic compounds. Their core structures are widely found in natural products and synthetic drugs, and have rich physiological and pharmacological activities, such as anti-tumor, anti-virus, anti-inflammation, and anti-infection. , antidepressant, etc., have important research value in the field of medicine. [0003] Due to their rich pharmacological activities, the synthesis and utilization of quinazolinone compounds have attracted extensive attention from chemists and biologists. The traditional synthesis method of quinazolinone mainly adopts metal-catalyzed heating reaction. These methods often require harsh reaction conditions. In addition, the addition of strong oxidants (such as potassium ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/91C07D401/04C07D409/04
CPCC07D239/91C07D401/04C07D409/04
Inventor 张方林王健
Owner WUHAN UNIV OF TECH
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