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One-pot method for preparing 3-trifluoromethylisoxazole compound

A technology of isoxazole compounds and trifluoromethyl, which is applied in the field of preparation of isoxazole compounds, can solve the problems of harsh reaction conditions, low utilization rate of raw materials, lengthy reaction steps, etc., and achieves less side reactions, is conducive to environmental protection, Simple operation effect

Active Publication Date: 2021-06-11
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • One-pot method for preparing 3-trifluoromethylisoxazole compound

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 HNMR (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 one-pot method for preparing 3-trifluoromethyl-substituted isoxazole compounds. The method is to prepare fluorodiazomethane from commercially available trifluoroethylamine, and then It is obtained by coupling reaction with alkyne compounds under the catalysis of cheap copper; the method is simple to operate, mild in reaction conditions, low in cost, less by-products, high in yield, high in functional group tolerance, and can scale up the reaction. At the same time, a more in-depth mechanism study was made, and the mechanism of the intermediate of trifluoromethyl ketoxime compound in the reaction was 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 Patents(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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