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Preparation method of polyfluoroalkyl substituted isoxazole

A technology of polyfluoroalkyl and polyfluoroalkyl fingers, which is applied in the field of preparing polyfluoroalkyl-substituted isoxazole compounds, and can solve problems such as poor selectivity, by-products, and cumbersome synthesis steps of raw materials

Inactive Publication Date: 2019-09-20
RENMIN UNIVERSITY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods have the following two problems that are not easy to solve: 1), the raw material synthesis steps are loaded down with trivial details; 2) the selectivity is poor, often accompanied by the generation of by-products

Method used

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  • Preparation method of polyfluoroalkyl substituted isoxazole
  • Preparation method of polyfluoroalkyl substituted isoxazole
  • Preparation method of polyfluoroalkyl substituted isoxazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0120] Preparation of 3-perfluoropropyl-5-phenylisoxazole

[0121] In the Shrek bottle, under the condition of nitrogen protection, add Co(acac) in sequence 2 (0.05mmol), NaN 3 2 (1.5mmol), DABCO (1.5mmol), styrene 1 (0.5mmol), perfluoroiodobutane 3 (1.0mmol), n-hexane-tetrahydrofuran (1.6ml-0.4ml). Make it warm up to 80°C freely, and react for 12 hours. After the reaction was completed, it was evaporated by rotary evaporation and passed through the column. After weighing, 123mg of the product was obtained with a yield of 79%.

[0122] figure 1 For the proton nuclear magnetic resonance spectrogram of the product that prepares, characterize as follows:

[0123] 1 H NMR (600MHz, CDCl 3 )δ7.73-7.71(m,2H),7.42-7.41(m,3H),6.66(s,1H).

[0124] It was confirmed that the prepared product was 3-perfluoropropyl-5-phenylisoxazole.

[0125] When different catalysts and solvents are used, the isoxazole compound (3-perfluoropropyl-5-phenylisoxazole) can also be obtained.

[0126] W...

Embodiment 2

[0134] Preparation of 3-perfluoropropyl-5-(4-tert-butyl)phenylisoxazole

[0135] In the Shrek bottle, under the condition of nitrogen protection, add Co(acac) in sequence 2 (0.05mmol), NaN 3 2 (1.5mmol), DABCO (1.5mmol), 4-tert-butylstyrene 1 (0.5mmol), perfluoroiodobutane 3 (1.0mmol), n-hexane-tetrahydrofuran (1.6ml-0.4ml). Make it warm up to 80°C freely, and react for 12 hours. After the reaction was completed, it was evaporated by rotary evaporation and passed through the column. After weighing, 156 mg of the product was obtained with a yield of 85%.

[0136] figure 2 For the proton nuclear magnetic resonance spectrum figure of the product that prepares ( 1 HNMR), characterized as follows:

[0137] 1 H NMR (600MHz, CDCl 3 )δ7.66(d, J=8.5Hz, 2H), 7.44(d, J=8.5Hz, 2H), 6.62(s, 1H), 1.27(s, 9H);

[0138] It was confirmed that the prepared product was 3-perfluoropropyl-5-(4-tert-butyl)phenylisoxazole.

Embodiment 3

[0140] Preparation of 3-perfluoropropyl-5-(4-methoxy)phenylisoxazole

[0141] In the Shrek bottle, under the condition of nitrogen protection, add Co(acac) in sequence 2 (0.05mmol), NaN 3 2 (1.5mmol), DABCO (1.5mmol), 4-methoxystyrene 2 (0.5mmol), perfluoroiodobutane 3 (1.0mmol), n-hexane-tetrahydrofuran (1.6ml-0.4ml). Make it warm up to 80°C freely, and react for 12 hours. After the reaction was completed, it was evaporated by rotary evaporation and passed through the column. After weighing, 137 mg of the product was obtained, and the yield was 80%.

[0142] image 3 For the proton nuclear magnetic resonance spectrum figure of the product that prepares ( 1 HNMR), characterized as follows:

[0143] 1 H NMR (600MHz, CDCl 3 ) δ 7.66 (d, J = 8.7Hz 2H), 6.91 (d, J = 8.8Hz, 2H), 6.53 (s, 1H), 3.78 (s, 3H).

[0144] It was confirmed that the prepared product was 3-perfluoropropyl-5-(4-methoxy)phenylisoxazole.

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Abstract

The invention provides a preparation method of polyfluoroalkyl substituted isoxazole. According to the preparation method, a compound (1), a compound (2), and a compound (3) carry out reactions to obtain the polyfluoroalkyl substituted isoxazole represented by a formula (1). The synthesis method is simple and easy to perform; the raw materials and catalysts are cheap and easily available; the polyfluoroalkyl substituted isoxazole is obtained through one-step reaction; and moreover, different fluoroalkyl groups can be introduced into an isoxazole structure. The provided preparation method of polyfluoroalkyl substituted isoxazole has the advantages of simple synthesis route, high yield, and low cost.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing polyfluoroalkyl-substituted isoxazole compounds. Background technique [0002] Isoxazole structures widely exist in natural products. At the same time, many biologically active compounds contain isoxazole structures. Therefore, methods for synthesizing isoxazoles have been continuously developed. However, there are still many problems in the existing methods, such as the raw materials are not easy to obtain, multi-step synthesis is required, and the operation is cumbersome. In particular, when fluoroalkyl groups need to be introduced, it is more difficult to synthesize. In other words, the existing methods for synthesizing isoxazoles mainly include: condensation of alkyne oxime and α-carbonyl oxime compound or cycloaddition of isocyanide oxide and alkyne. When synthesizing fluoroalkyl-substituted isoxazoles, it is usually first to ...

Claims

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Application Information

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IPC IPC(8): C07D261/08C07D413/04C07D413/10
CPCC07D261/08C07D413/04C07D413/10
Inventor 李志平陈元金
Owner RENMIN UNIVERSITY OF CHINA
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