Method for preparing 3-trifluoromethylisooxazole compound by one-pot

A technology of isoxazole compound and trifluoromethyl, which is applied in the field of preparation of isoxazole compound, can solve the problems of low utilization rate of raw materials, lengthy reaction steps, harsh reaction conditions, etc., and achieve reduced production cost, simple operation, and side effects less responsive effect

Active Publication Date: 2018-04-27
JIANGXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0010] In view of the existing problems in the synthesis process of 3-trifluoromethylisoxazole, such as the shortcomings of lengthy reaction steps, low raw material utilization rate and harsh reaction conditions, the purpose of the present invention is to provide an efficient A method for synthesizing 3-trifluoromethylisoxazole heterocyclic compounds with easy-to-obtain raw materials, mild reaction conditions, high product yield and few by-products. This method designs and synthesizes 3-trifluoromethylisoxazole with a new structure Oxazole, providing a raw material source for drug screening and new drug synthesis

Method used

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  • Method for preparing 3-trifluoromethylisooxazole compound by one-pot
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  • Method for preparing 3-trifluoromethylisooxazole compound by one-pot

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Substrate: 4-Phenylphenylacetylene

[0034] product:

[0035] Product characterization data: pale yellow solid (60.7mg, 84% yield); mp: 128.5–129.5; 1 H NMR (400MHz, CDCl 3 )δ7.88(d, J=8.0Hz, 2H), 7.73(d, J=8.0Hz, 2H), 7.64(d, J=8.0Hz, 2H), 7.49(t, J=8.0Hz, 2H) ,7.42(d,J=8.0Hz,1H),6.77(s,1H); 13 C NMR (100MHz, CDCl 3 )δ172.5, 156.4 (q, J=38.0Hz), 144.4, 140.0, 129.4, 128.6, 128.2, 127.4, 126.8, 125.2, 120.1 (q, J=270.0Hz), 97.1; 19 F NMR (376MHz, CDCl 3 )δ-63.19(s,3F); 19 F{ 1 H}NMR (376MHz, CDCl 3)δ-63.19(s,3F); HRMS(ESI)m / z calcd for C 16 h 11 ONF 3 + [M+H] + 290.0787,found 290.0784.

Embodiment 2

[0037] Substrate: Phenylacetylene

[0038] product:

[0039] Product characterization data: pale yellow solid (46.7mg, 88% yield); mp: 44.4–45.2; 1 H NMR (400MHz, CDCl 3 )δ7.83–7.78(m,2H),7.53–7.50(m,3H),6.74(s,1H); 13 C NMR (100MHz, CDCl 3 )δ172.8, 156.4 (q, J=38.0Hz), 131.6, 129.6, 126.4, 120.1 (q, J=270Hz), 97.1; 19 FNMR (376MHz, CDCl 3 )δ-63.27(s,3F); 19 F { 1 H}NMR (376MHz, CDCl 3 )δ-63.27(s,3F); HRMS(ESI)m / zcalcd for C 10 h 7 ONF 3 + [M+H] + 214.0474,found 214.0471.

Embodiment 3

[0041] Substrate: 4-methylphenylacetylene

[0042] product:

[0043] Product characterization data: white solid (49.6mg, 87% yield); mp: 71.6–72.3; 1 H NMR (400MHz, CDCl 3 )δ7.69(d, J=8.0Hz, 2H), 7.30(d, J=8.0Hz, 2H), 6.68(s, 1H), 2.42(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ173.0, 156.3 (q, J = 38.0Hz), 142.2, 130.3, 126.3, 123.8, 120.1 (q, J = 270.0Hz), 96.5, 21.8; 19 F NMR (376MHz, CDCl 3 )δ-63.30(s,3F); 19 F{ 1 H}NMR (376MHz, CDCl 3 )δ-63.30(s,3F); HRMS(ESI)m / z calcd for C 11 h 9 ONF 3 + [M+H] + 228.0631, found 228.0628. [13]

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Abstract

The invention discloses a novel method for preparing a 3-trifluoromethylisooxazole compound by one-pot. According to the method, trifluoroethylamine which can be purchased in markets is prepared intofluorinated diazomethane, and then the fluorinated diazomethane and an alkynes compound are in coupled reaction under catalysis of low-price copper. The method is simple to operate, reaction conditions are mild, the cost is low, by-products are fewer, the yield is high, tolerance of a functional group is high, and reaction can be amplified. Meanwhile, much deeper mechanism study is carried out, and a mechanism that a trifluoromethyl ketoximes compound intermediate may be produced in the reaction is proposed.

Description

technical field [0001] The present invention relates to a preparation method of a 3-trifluoromethyl-substituted isoxazole compound, in particular to a method for preparing a 3-trifluoromethyl-substituted isoxazole compound using trifluoroethylamine and a terminal alkyne as raw materials. It belongs to the technical field of organofluorine chemistry and pharmaceutical intermediate synthesis. Background technique [0002] The introduction of trifluoromethyl groups into organic compounds can improve the polarity, dipole moment, stability and lipophilicity of target products, so compounds containing trifluoromethyl groups are useful in the fields of medicine, pesticides and new functional materials. Significance. Isoxazole heterocyclic skeletons are not only widely distributed in many active drug molecules, but also are important intermediates in organic synthetic chemistry. However, trying to introduce a trifluoromethyl group at the 3rd position in the isoxazole skeleton can ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/08C07D413/04C07F7/18
CPCC07D261/08C07D413/04C07F7/1804
Inventor 章晓炜胡文丽陈锁胡祥国
Owner JIANGXI NORMAL UNIV
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