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Dihydrofuran quinolinone derivative and preparation method thereof

A technology of dihydrofuran quinolinone and its derivatives, applied in the direction of organic chemistry, which can solve the problems of metal residues and cumbersome steps, and achieve the effects of mild conditions, simple methods, and convenient operation

Pending Publication Date: 2021-08-17
HARBIN INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention aims to solve the technical problems of metal residues and cumbersome steps in the existing synthesis method of dihydrofuran quinolinone compounds and provide a dihydrofuran quinolinone derivative and a preparation method thereof

Method used

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  • Dihydrofuran quinolinone derivative and preparation method thereof
  • Dihydrofuran quinolinone derivative and preparation method thereof
  • Dihydrofuran quinolinone derivative and preparation method thereof

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Embodiment 1

[0031] Embodiment 1: the preparation method of the dihydrofuran quinolinone derivative of the present embodiment, carry out according to the following steps:

[0032] Add 0.0309 g (0.1 mmol) of the 1,7-enyne substrate (N-(2-(((4-fluorophenyl)ethynyl)phenyl)-2-(hydroxymethyl) to a 10 mL penicillin bottle -N-methacrylamide), 0.0304g (1.5mmol) of BrCF 2 CO 2 Et, 0.0032g mole percent concentration is the photocatalyst fac-Ir(ppy) of 5mol% 3 , 0.0652g (0.2mmol) of cesium carbonate; with a volume of 1mL of acetone as a reaction solvent, in N 2 Under the atmosphere, the reaction was stirred under 60W blue LED at room temperature for 2 h. After the reaction is completed, the reaction solvent is concentrated and spin-dried by a rotary evaporator, and then a mixed solution of petroleum ether: ethyl acetate with a volume ratio of 20:1 is used as an eluent to carry out purification and separation by silica gel column chromatography to obtain dihydrofuran Quinolinone derivatives. The ...

Embodiment 2

[0036] Embodiment 2: the preparation method of the dihydrofuran quinolinone derivative of the present embodiment, carry out according to the following steps:

[0037] Add 0.0305 g (0.1 mmol) of the 1,7-enyne substrate (2-(hydroxymethyl)-N-methyl-N-(2-(p-tolylethynyl)phenyl) to a 10 mL penicillin bottle Acrylamide), 0.0304g (1.5mmol) of BrCF 2 CO 2 Et, 0.0032g mole percent concentration is the photocatalyst fac-Ir(ppy) of 5mol% 3 , 0.0652g (0.2mmol) of cesium carbonate; with a volume of 1mL of acetone as a reaction solvent, in N 2 Under the atmosphere, the reaction was stirred under 60W blue LED at room temperature for 2 h. After the reaction is completed, the reaction solvent is concentrated and spin-dried by a rotary evaporator, and then a mixed solution of petroleum ether: ethyl acetate with a volume ratio of 20:1 is used as an eluent to carry out purification and separation by silica gel column chromatography to obtain dihydrofuran Quinolinone derivatives. The chemical...

Embodiment 3

[0041] Embodiment 3: the preparation method of the dihydrofuran quinolinone derivative of the present embodiment, carry out according to the following steps:

[0042] Add 0.0321 g (0.1 mmol) of 1,7-enyne substrate (2-(hydroxymethyl)-N-(2-(((4-methoxyphenyl)ethynyl)benzene base)-N-methacrylamide), 0.0304g (1.5mmol) of BrCF 2 CO 2 Et, 0.0032g (5mol%) photocatalyst fac-Ir (ppy) 3 , 0.0652g (0.2mmol) of cesium carbonate; with a volume of 1mL of acetone as a reaction solvent, in N 2 Under the atmosphere, the reaction was stirred under 60W blue LED at room temperature for 2 h. After the reaction is completed, the reaction solvent is concentrated and spin-dried by a rotary evaporator, and then a mixed solution of petroleum ether: ethyl acetate with a volume ratio of 20:1 is used as an eluent to carry out purification and separation by silica gel column chromatography to obtain dihydrofuran Quinolinone derivatives, its reaction formula is:

[0043]

[0044] The purity of the p...

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Abstract

The invention discloses a dihydrofuran quinolinone derivative and a preparation method thereof, relates to a dihydrofuran quinolinone derivative and a preparation method thereof, and aims to solve the technical problems of metal residues and tedious steps in the existing synthesis method of a dihydrofuran quinolinone compound. The structural formula of the dihydrofuran quinolinone derivative is shown in the specification, wherein R1 is alkoxy, halogen, alkyl, H or substituted aryl; and R2 is alkoxy, halogen, alkyl or H. The preparation method comprises the following steps: dissolving a 1, 7-eneyne substrate, ethyl bromodifluoroacetate, a photocatalyst and alkali in an organic solvent, uniformly mixing the mixture, carrying out an illumination reaction under a blue LEDs lamp, carrying out rotary evaporation on the solvent, and carrying out separation and purification to obtain the dihydrofuran quinolinone derivative. The compound can be used as a drug lead compound, and can be used in the fields of biological activity test research and synthesis.

Description

technical field [0001] The invention relates to dihydrofuran quinolinone derivatives and a preparation method thereof, belonging to the field of organic synthesis. Background technique [0002] As an important molecular skeleton, quinolinone widely exists in biologically active natural products and drug molecules. It is a very important class of polycyclic compounds, showing antitumor, antimicrobial, antioxidative, and antiasthmatic properties. , anticoagulant, antiviral and anti-inflammatory and other important medical value. The figure below shows the structural formulas of several reported drugs containing furoquinoline rings. Therefore, this class of compounds has received extensive attention from many organic chemists. Its bicyclic skeleton has photoelectric properties and lipid-lowering activity, and they are also used in food additives and cosmetics. Similarly, the furan ring is also a special heterocyclic skeleton in nature, which widely exists in many natural and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048
CPCC07D491/048
Inventor 高国林邹繁月姜再兴卓王涛
Owner HARBIN INST OF TECH
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