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Method for synthesizing 4-amide isooxazole

A technology for isoxazole and amide, which is applied in the field of synthesizing 4-amidoisoxazole, can solve the problems that 4-amidoisoxazole derivatives have not been directly synthesized, and achieve a wide range of substrate universality, The method is simple and easy, and the effect of mild reaction conditions

Active Publication Date: 2020-02-04
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although great progress has been made in the synthesis of multifunctional isoxazole derivatives, there is no report on the direct synthesis of 4-amidoisoxazole derivatives.

Method used

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  • Method for synthesizing 4-amide isooxazole
  • Method for synthesizing 4-amide isooxazole
  • Method for synthesizing 4-amide isooxazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] In a 15mL round bottom flask, add 0.003mol bis(acetonitrile) dichloropalladium, 2 equivalents of sodium iodide, 0.10mmol 1,3-diphenyl O-methyl acetylenone oxime ether, 0.40mmol isopropylamine, 1mL DMSO, filled with carbon monoxide balloon, stirred and reacted at 40°C for 12 hours, stopped heating and stirring, cooled to room temperature, and distilled under reduced pressure to obtain the crude product, and then separated and purified by column chromatography to obtain the target product, which was eluted by column chromatography The liquid is petroleum ether with a volume ratio of 20:1: ethyl acetate mixed solvent, and the yield is 15%.

Embodiment 2

[0034] In a 15mL two-necked round bottom flask, add 0.003mol allyl palladium chloride dimer, 2 equivalents of sodium iodide, 0.10mmol 1,3-diphenyl O-methyl acetylene ketoxime ether, 0.40mmol isopropyl Amine, 1mL DMSO, filled with a carbon monoxide balloon, stirred at 40°C for 12 hours, stopped heating and stirring, cooled to room temperature, and distilled under reduced pressure to obtain a crude product, which was then separated and purified by column chromatography to obtain the target product. The eluent was analyzed as petroleum ether:ethyl acetate mixed solvent with a volume ratio of 20:1, and the yield was 11%.

Embodiment 3

[0036] Add 0.003mol of bis(pyridine)palladium dichloride, 2 equivalents of sodium iodide, 0.10mmol of 1,3-diphenyl O-methyl acetylene ketone oxime ether, 0.40mmol of isopropylamine in a 15mL two-neck round bottom flask, 1mL DMSO, filled with carbon monoxide balloon, stirred and reacted at 40°C for 12 hours, stopped heating and stirring, cooled to room temperature, and distilled under reduced pressure to obtain the crude product, then separated and purified by column chromatography to obtain the target product, the column chromatography used The deliquification was petroleum ether: ethyl acetate mixed solvent with a volume ratio of 20:1, and the yield was 30%.

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Abstract

The invention belongs to the technical field of organic synthesis and discloses a method for synthesizing 4-amide isooxazole. The method comprises the following steps: adding a palladium salt catalyst, additives, O-methyl acetylene ketoxime ether of a structure of a formula (1) shown in the description, amine of a structure of a formula (2) shown in the description and an organic solvent into a reactor, injecting carbon monoxide, performing a stirring reaction at 40-80 DEG C, and performing separation and purification on the reaction product, so as to obtain 4-amide isooxazole of a structure of a formula (3) shown in the description. According to the method, palladium salt is adopted as the catalyst, O-methyl acetylene ketoxime ether and amine are adopted as raw materials, and the carbon monoxide is injected to implement a serial reaction of three components to synthesize the 4-amide isooxazole by using a "one step" method. The type diversity of the 4-amide isooxazole is expanded. In addition, all raw materials are cheap and easy to obtain, and the method is simple and feasible, good in functional group tolerance, wide in substrate universal range, mild in reaction condition, simple and safe in operation and good in industrial application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing 4-amidoisoxazole. Background technique [0002] The isoxazole heterocyclic skeleton is an important part of many drug molecules and bioactive molecules, and is widely used in organic synthesis, materials, fine chemicals and other fields. Moreover, multi-substituted isoxazoles are important structural units of many natural products, bioactive molecules and drug molecules. (M.G.Perronea, P.Vitalea, A.Panella, C.G.Fortuna, A.Scilimati, Eur.J.Med.Chem., 2015, 94, 252-264; S.A.Laufer, S.Margutti, M.D.Fritz, ChemMedChem, 2006, 1, 197- 207; A. Severin, K. Tabei, F. Tenover, M. Chung, N. Clarke, A. Tomasz, J. Biol. Chem., 2004, 279, 3398-3407; G.G. Gamber, E. Meredith, Q. Zhu, W. Yan, C, Rao, M. Capparelli, R. Burgis, I. Enyedy, J.-H. Zhang, N. Soldermann, K. Beattie, O. Rozhitskaya, K. A. Koch, N. Pagratis, V. Hosagrahara, R.B. Vega, T....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/18C07D409/12
CPCC07D261/18C07D409/12
Inventor 李建晓余俊生吴瑶丹唐浩莫依婷江焕峰
Owner SOUTH CHINA UNIV OF TECH
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