Method for preparing isoxazolo-isoquinolinone derivative under electro-catalysis

A technology of isoquinolone and isoxazole, which is applied in the field of preparation of isoxazoloisoquinolinone derivatives under electrocatalysis, can solve problems such as toxic solvents, long reaction time, and use of metal catalysts, so as to avoid Side reactions, simple synthesis method, fast response effect

Active Publication Date: 2019-12-03
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The above-mentioned method has obvious defects such as the use of metal catalysts and toxic solvents, long reaction times, etc.

Method used

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  • Method for preparing isoxazolo-isoquinolinone derivative under electro-catalysis
  • Method for preparing isoxazolo-isoquinolinone derivative under electro-catalysis
  • Method for preparing isoxazolo-isoquinolinone derivative under electro-catalysis

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of Isoxazoloisoquinolinone Derivative 2a

[0023]

[0024] Add N-alkoxybenzamide 1a (0.1mmol, 26.5mg) and tetra-n-butyl ammonium hexafluorophosphate (0.1mmol, 38.7mg) into a 10mL electrolytic cell without a diaphragm, and both cathode and anode electrodes use graphite felt electrodes ( 2cm x 1cm x 0.5cm). Afterwards, the system was filled with nitrogen, and 95% ethanol (5 mL) was added. Electrolysis was carried out at 80°C and a constant current of 2mA, and the reaction was carried out for 4h. After the reaction is complete, use a rotary evaporator to remove the solvent to obtain a crude product, which is separated by column chromatography (200-300 mesh silica gel, petroleum ether / ethyl acetate=1 / 1), and use a rotary evaporator to remove the solvent to obtain the target product The yield of the unsubstituted isoxazoloisoquinolinone derivative 2a is 93%.

[0025] Spectral analysis data 2a:

[0026] 1 H NMR (CDCl 3 ,400MHz):δ8.54(d,J=7.1Hz,1H),7.59-7....

Embodiment 2

[0028] Replace 1a in Example 1 with 1b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0029]

[0030] Spectrum analysis data 2b:

[0031] 1 H NMR (500MHz, CDCl 3 ):δ8.51(d,J=8.0Hz,1H),7.56(d,J=7.6Hz,1H),7.40-7.32(m,4H),7.27(d,J=6.7Hz,2H),4.54 (t, J=7.6Hz, 2H), 3.24(t, J=7.6Hz, 2H); 13 C NMR (125MHz, CDCl 3 )δ153.12, 137.66, 135.25, 135.03, 132.48, 130.51, 130.18, 128.78, 128.24, 127.67, 126.94, 126.47, 111.44, 69.50, 33.19.

Embodiment 3

[0033] Replace 1a in Example 1 with 1c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0034]

[0035] Spectrum analysis data 2c:

[0036] 1 H NMR (500MHz CDCl 3 ):δ8.47(d,J=3.6Hz,1H),7.53-7.49(m,2H),7.48–7.42(m,2H),7.34-7.28(m,3H),4.58(t,J=7.6 Hz,2H),3.39(t,J=7.6Hz,2H); 13 C NMR (125MHz, CDCl 3 ): δ152.76, 134.51, 134.43, 132.89, 132.53, 132.02, 130.14, 129.01, 128.29, 127.29, 126.71, 126.34, 112.60, 69.69, 32.36

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a method for preparing an isoxazolo-isoquinolinone derivative under electro-catalysis. The method comprises the following steps of adding a substituted N-alkoxy benzamide substance and tetra-n-butyl ammonium hexafluorophosphate with a molar ratio of 1 : 1 into a reactor, adding 95% ethanol as a solvent, and promotinga reaction to be carried out through the electro-catalysis strategy; and after the reaction is finished, carrying out concentration by a rotary evaporator to obtain a crude product, and carrying out silica gel column chromatography separation to obtain a target product. The synthesis method of the polysubstituted isoxazolo-isoquinolinone derivative has the characteristics of scientificity and reasonability, environment-friendly synthesis way and no metal catalyst; the reaction solvent is the 95% ethanol, and replaces a toxic solvent; a substrate can react under a weak current; the synthesis method is simple and rapid in reaction; and the yield of a target compound is high, and the derivative is easy to purify. A reaction equation is as shown in the description.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of isoxazoloisoquinolinone derivatives under electrocatalysis. Background technique [0002] Isoquinolones and isoxazoles are widely found in nature, and their derivatives have various biological activities and medicinal value: such as antihypertensive, antiarrhythmic, antitumor, antidepressant, antibacterial, antithrombotic, Various biological activities such as dilating blood vessels; 16,3180.) Isoxazole structures also exist in many drug molecules such as cloxacillin, valdecoxib, oxacillin, flucloxacillin, danazol, and dicloxacillin. ((a) J. Med. Chem. 2000, 43, 775-777. (b) J. Med. Chem. 2000, 43, 1661-1663. (c) J. Heterocycl. Chem. 1976, 13, 449-453.) [0003] Isoxazoloisoquinolinone derivatives, as a combination of two compounds, isoquinolinone and isoxazole, are likely to have the biological activity and medicinal value of these...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/00
CPCC25B3/00
Inventor 张林宝杜武博耿瑞森文丽荣李明
Owner QINGDAO UNIV OF SCI & TECH
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