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A kind of preparation method of isoxazoloisoquinolinone derivatives under electrocatalysis

A technology of isoquinolinone and isoxazole, which is applied in the field of preparation of isoxazoloisoquinolinone derivatives under electrocatalysis, can solve the problems of using metal catalysts, long reaction time, toxic solvents and the like, and achieves the reaction Fast, simple synthesis method, scientific and reasonable synthesis method

Active Publication Date: 2021-05-14
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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  • A kind of preparation method of isoxazoloisoquinolinone derivatives under electrocatalysis
  • A kind of preparation method of isoxazoloisoquinolinone derivatives under electrocatalysis
  • A kind of preparation method of isoxazoloisoquinolinone derivatives under electrocatalysis

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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-butylammonium 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),7.59-7.4...

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 discloses a preparation method of isoxazoloisoquinolinone derivatives under electrocatalysis, which belongs to the technical field of organic synthesis. The method is as follows: into the reactor, add substituted N-alkoxybenzamides and tetra-n-butylammonium hexafluorophosphate with a molar ratio of 1:1, add 95% ethanol as a solvent, and use an electrocatalytic strategy to promote the reaction. After the reaction was completed, the crude product was obtained by concentrating with a rotary evaporator, and then separated by silica gel column chromatography to obtain the target product. The synthesis method of the multi-substituted isoxazoloisoquinolinone derivative provided by the invention is scientific and reasonable, and the synthesis route is green and environment-friendly without metal catalyst; the reaction solvent is 95% ethanol instead of the toxic solvent; the substrate is ready to use under weak current It can be reacted; the synthesis method is simple, the reaction is fast; the yield of the target compound is high, and the product is easy to purify. Its reaction equation is as follows:

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 Patents(China)
IPC IPC(8): C25B3/05C25B3/07C25B3/09
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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