Dihydroquinazoline-4 (1H)-ketone compound and preparation method thereof
Dihydroquinazolin-4 (1H)-one compounds were synthesized at room temperature by electrochemical methods, which solved the problems of complex operation and high energy consumption in the existing technology and achieved efficient, green and economical synthesis effects.
Patent Information
- Application Number
- CN202511030504.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-07-25
- Publication Date
- 2025-09-16
AI Technical Summary
The existing technology for preparing dihydroquinazolin-4 (1H)-one compounds is complex, relies on high temperature and high energy consumption, requires transition metal catalysis and external redox agents, and has a limited substrate range.
A transition metal-free, external redox-free electrochemical method was employed. Using magnesium and graphite rods as electrodes, quinazolinone and electron-deficient olefins were electrolyzed at room temperature to synthesize dihydroquinazolin-4(1H)-one compounds via current reaction.
The efficient synthesis of dihydroquinazolin-4 (1H)-one compounds under mild conditions has been achieved with high yield, wide applicability, compliance with green chemistry principles, and energy and time savings.
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Figure CN120649033A_ABST
Abstract
Claims
1. A dihydroquinazoline-4 (1H) -one compound, characterized in that Having any one of formulas (I) to (XX): 。 2. A method for preparing the dihydroquinazoline-4(1H)-one compound as claimed in claim 1, comprising the following steps: Equipped with a magnesium rod as an anode electrode and a graphite rod as a cathode electrode, quinazolinone, electron-deficient olefin, electrolyte and mixed solvent are added at room temperature, and current is passed through the stirring reaction to obtain dihydroquinazolin-4 (1H)-one compounds.
3. The preparation method according to claim 2, characterized in that In the step, the quinazolinone is any one of quinazolin-4 (3H) -one, 7-chloroquinazolin-4 (3H) -one, 6-methoxyquinazolin-4 (3H) -one, 5-methylquinazolin-4 (3H) -one, 6-chloro-8-methylquinazolin-4 (3H) -one, 3-methylquinazolin-4 (3H) -one, 3-isopropylquinazolin-4 (3H) -one or 3-phenylquinazolin-4 (3H) -one.
4. The preparation method according to claim 2, characterized in that In the step, the electron-deficient olefin is any one of ethyl acrylate, methyl acrylate, acrylic acid, 1-ethyl methacrylate, 2-ethyl methacrylate, 2-phenylethyl acrylate, N-ethylacrylamide, dimethyl acrylamide, N-(hydroxymethyl)acrylamide, acrylamide, N-(m-tolyl)acrylamide, N-(m-fluorophenyl)acrylamide or N-(o-chlorophenyl)acrylamide.
5. The preparation method according to claim 2, characterized in that In the step, the electrolyte is any one of ammonium iodide, sodium iodide, tetrabutylammonium iodide, tetrabutylammonium tetrafluoroborate or tetrabutylammonium bromide.
6. The preparation method according to claim 2, characterized in that In the step, the reaction is carried out in a mixed solvent, which includes a first solvent and a second solvent; the first solvent is acetonitrile or ethanol; and the second solvent is any one of acetic acid, trifluoroacetic acid or hexafluoroisopropanol.
7. The method for preparing dihydroquinazoline-4(1H)-one compounds according to claim 6, wherein The volume ratio of the first solvent to the second solvent is (5-8):
1.
8. The preparation method according to claim 3, characterized in that In the step, the reaction current is 5-20 mA.
9. The preparation method according to claim 3, characterized in that In the step, the reaction time is 2 to 8 h.
10. The preparation method according to claim 3, characterized in that In the step, the molar ratio of the quinazolinone, the electron-deficient olefin, the electrolyte and the mixed solvent is 1: (0.8-2): (0.5-1.5): (0.5-1).