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A kind of preparation method of 3-hydroxymethyl-4-phenyl-3,4-dihydroquinolinone compound

A technology of dihydroquinolinone and compound is applied in the field of preparation of 3-hydroxymethyl-4-phenyl-3,4-dihydroquinolinone compound, and achieves mild reaction conditions, excellent application value and easy operation. Effect

Active Publication Date: 2022-05-17
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] But so far, there is no literature report on the direct synthesis of 3-hydroxymethyl-4-phenyl-3,4-dimethoxyl from cheap and easily available N-methyl-N-aryl-2-phenylacrylamide. Method for Hydroquinolinone Compounds

Method used

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  • A kind of preparation method of 3-hydroxymethyl-4-phenyl-3,4-dihydroquinolinone compound
  • A kind of preparation method of 3-hydroxymethyl-4-phenyl-3,4-dihydroquinolinone compound
  • A kind of preparation method of 3-hydroxymethyl-4-phenyl-3,4-dihydroquinolinone compound

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Experimental program
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Effect test

Embodiment 1～4

[0040] The following examples 1 to 4 all react according to the following reaction equation, mainly to investigate the yield situation of different substrates reacting under optimal conditions:

[0041]

[0042]The specific operation steps are: in a 10mL round bottom flask, add N-methyl-N-aryl-2-phenylacrylamide (0.5mmol), potassium monopersulfate (0.75mmol), acetonitrile (2.5mL) successively . The resulting mixture was stirred and reacted at 90° C., and the reaction progress was followed by thin-layer chromatography, and the reaction time was generally 24 hours. After the reaction, the extract was concentrated by a rotary evaporator, and purified by column chromatography using petroleum ether / ethyl acetate as eluent.

Embodiment 1

[0044] Compound 1, yield 70%, 3-hydroxy-1-methyl-4-phenyl-3,4-dihydroquinolin-2(1H)-one;

[0045]

[0046] 1 H NMR (400MHz, CDCl 3 ,ppm)δ7.47–7.43(m,2H),7.39–7.28(m,4H),7.07 (dd,J=8.1,1.2Hz,1H),6.98(td,J=7.6,1.2Hz,1H) ,6.66(dt,J=7.8,1.4Hz,1H), 4.52(d,J=13.2Hz,1H),4.12(d,J=13.2Hz,1H),3.90(s,1H),3.51(s, 3H);

[0047] 13 C NMR (100MHz, CDCl 3 , ppm) δ171.5, 138.9, 138.0, 129.3, 129.0, 128.5, 128.2, 128.1, 127.7, 123.9, 114.9, 70.0, 49.3, 30.5;

[0048] HRMS(ESI)m / z Calcd for C 16 h 15 NO 2 + [M + ]: 253.1103; found: 253.1105.

Embodiment 2

[0050] Compound 2, yield 76%,

[0051] 3-hydroxy-1,6-dimethyl-4-phenyl-3,4-dihydroquinolin-2(1H)-one;

[0052]

[0053] 1 H NMR (400MHz, CDCl 3 ,ppm)δ7.48–7.44(m,2H),7.40–7.36(m,1H),7.35–7.30(m,2H),7.10(d,J=8.4Hz,1H),6.96(d,J= 8.4Hz, 1H), 6.45(s, 1H), 4.48(d, J=13.6Hz, 1H), 4.08(d, J=13.6Hz, 1H), 3.92(d, 1H), 3.48(s, 3H) ,2.18(s,3H);

[0054] 13 C NMR (100MHz, CDCl 3 , ppm) δ171.3, 138.1, 136.5, 133.6, 129.3, 129.0, 129.0, 128.6, 127.9, 127.6, 114.8, 70.1, 49.3, 30.5, 20.7

[0055] HRMS(ESI)m / z Calcd for C 17 h 17 NO 2 + [M + ]: 267.1259; found: 267.1261.

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Abstract

The invention discloses a preparation method of 3-hydroxymethyl-4-phenyl-3,4-dihydroquinolinone compound. The method uses acetonitrile as the reaction medium, and potassium monopersulfate promotes the epoxidation of N-methyl-N-aryl-2-phenylacrylamide-intramolecular Friedel-Crafts alkylation series reaction to generate 3-hydroxymethyl ‑4‑phenyl‑3,4‑dihydroquinolinone compound; the method has the advantages of mild conditions, simple operation, environmental protection, easy access to raw materials, excellent compatibility of substrate functional groups, and high reaction yield.

Description

technical field [0001] The present invention relates to a preparation method of 3-hydroxymethyl-4-phenyl-3,4-dihydroquinolinone compound, in particular to the promotion of N Synthesis of 3-Hydroxymethyl-4-Phenyl-3,4-Dihydroquinolinone by Epoxidation of -Methyl-N-aryl-2-Phenylacrylamide-Intramolecular Friedel-Crafts Alkylation Series Reaction The compound method belongs to the technical field of organic intermediate synthesis. Background technique [0002] 3,4-Dihydroquinolinone exists in a variety of natural products and synthetic drugs, and has good biological and pharmacological activities. It is of great research significance to develop new preparation methods for this type of compound. The hydroxymethyl functional group can effectively improve the metabolic stability and bioavailability of bioactive molecules, and the development of new synthetic methods for heterocyclic compounds containing hydroxymethyl functional groups is of great significance for the development of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/22
CPCC07D215/22
Inventor 芦玲慧张明中何卫民基艳吴建平
Owner HUNAN UNIV OF SCI & ENG
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