Preparation method of isoxazole and isoquinoline ketone derivative

A technology of isoquinolinone and isoxazole, which is applied in the field of preparation of isoxazoloisoquinolinone derivatives, can solve the problems of high reaction temperature and long reaction time, and achieve simple synthesis method, easy product, and easy reaction fast effect

Inactive Publication Date: 2019-02-22
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] There are obvious disadvantages in the above-mentioned method for preparing isoxazoloisoquinolinone derivatives: the reaction temperature is higher and the reaction time is longer

Method used

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  • Preparation method of isoxazole and isoquinoline ketone derivative
  • Preparation method of isoxazole and isoquinoline ketone derivative
  • Preparation method of isoxazole and isoquinoline ketone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 1) Preparation of isoxazoloisoquinolinone derivative 2a

[0022]

[0023] Add N-alkoxybenzamide 1a (0.2mmol, 53.0mg), iodobenzene diacetate (0.2mmol, 64.4mg) into a 25ml round bottom flask, add hexafluoroisopropanol (4mL), stir at room temperature, React for 1 minute. 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 uses a rotary evaporator to remove the solvent to obtain the target The product is the unsubstituted isoxazoloisoquinolinone derivative 2a, and its yield is 92%.

[0024] Spectral analysis data 2a:

[0025] 1 H NMR (400MHz, CDCl 3 )δ8.54(d, J=7.1Hz, 1H), 7.50(tq, J=14.5, 7.2Hz, 5H), 7.36(t, J=7.7Hz, 3H), 4.58(t, J=7.6Hz, 2H), 3.39(t, J=7.6Hz, 2H). 13 C NMR (100MHz, CDCl 3 )δ153.95, 136.20, 135.02, 132.52, 131.63, 130.31, 128.93, 128.10, 127.47, 126.32, 124.71, 113.03, 69.55, 32.46.

Embodiment 2

[0027] Replace 1a in Example 1 with 1b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0028]

[0029] Spectrum analysis data 2b:

[0030] 1 H NMR (500MHz, CDCl 3 )δ8.34(s, 1H), 7.50(t, J=7.5Hz, 2H), 7.44(t, J=6.9Hz, 1H), 7.35(dd, J=12.4, 8.1Hz, 3H), 7.27( dd, J=5.9, 2.3Hz, 1H), 4.57(t, J=7.5Hz, 2H), 3.38(t, J=7.6Hz, 2H), 2.48(s, 3H). 13 C NMR (125MHz, CDCl 3 )δ153.90, 136.88, 133.90, 133.17, 131.51, 130.27, 128.86, 128.00, 127.00, 126.23, 124.65, 113.02, 109.98, 69.58, 32.32, 21.20.

Embodiment 3

[0032] Replace 1a in Example 1 with 1c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0033]

[0034] Spectrum analysis data 2c:

[0035] 1 H NMR (500MHz, CDCl 3 )δ7.90(d, J=2.7Hz, 1H), 7.47(t, J=7.3Hz, 2H), 7.42(t, J=7.4Hz, 1H), 7.35–7.30(m, 2H), 7.30– 7.25(m,1H),7.13(dd,J=9.0,2.7Hz,1H),4.56(t,J=7.5Hz,2H),3.91(s,3H),3.36(t,J=7.6Hz,2H ). 13 C NMR (125MHz, CDCl 3 )δ158.33, 153.42, 135.12, 130.19, 128.81, 127.97, 126.27, 122.21, 113.01, 107.13, 69.70, 55.71, 32.13.

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Abstract

The invention discloses a preparation method of a polysubstituted isoxazole and isoquinoline ketone derivative and belongs to the technical field of inorganic synthesis. The preparation method comprises the steps that substituted N-alkyl benzamide and iodobenzene diacetate are added into a reactor, after stirring reaction is completed in a solvent, filtrate is concentrated by using a rotary evaporator, thus a coarse product is obtained, the coarse product is subjected to chromatographic separation through a silica gel column, and thus a target compound is obtained. The synthesis method of thepolysubstituted isoxazole and isoquinoline ketone derivative has the characteristics that the synthesis method is scientific, reasonable and simple, the yield of the target compound is high, a productis easy to purify, reaction is fast, and the reaction temperature is the room temperature. A reaction equation of the polysubstituted isoxazole and isoquinoline ketone derivative is shown as the formula (please see the specifications for the formula).

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. Background technique [0002] Isoquinolinone compounds widely exist in nature, and many drugs or drug intermediates contain isoquinolinone structural units. Isoquinolinone compounds have biological activities such as antimalarial, insecticidal, antimicrobial, antitumor, antidepressant, antibacterial, analgesic and anti-inflammatory. ((a) Chem.Abstr.2012,157,356574.(b)Chem.Abstr.1983,98,71955.(c)Chem.Abstr.1969,71,112830.) The isoxazole structure widely exists in many natural Drugs, such as ibotenic acid, etc., and some drugs, including COX-2 inhibitor valdecoxib; lactamase-resistant antibiotics cloxacillin and flucloxacillin; steroid drugs danazol, etc. ((a) European Journal of Medicinal Chemistry, 2014, 77(22): 121-133. (b) Biochemical and Biophysical Research Communications, 2010, 391(1): 744-7...

Claims

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Application Information

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IPC IPC(8): C07D498/04
CPCC07D498/04
Inventor 张林宝耿瑞森文丽荣姚天宇李明
Owner QINGDAO UNIV OF SCI & TECH
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