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Polyfluoroalkenyl substituted oxazole compound and preparation method thereof

A polyfluoroalkenyl, compound technology, applied in organic chemistry and other directions, to achieve high step economy, mild reaction conditions, diverse functional group tolerance and substrate range.

Inactive Publication Date: 2020-10-09
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, there have been no reports of the formation of oxazole rings and the completion of polyfluoroalkenylation during the reaction by breaking multiple carbon-fluorine bonds.

Method used

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  • Polyfluoroalkenyl substituted oxazole compound and preparation method thereof
  • Polyfluoroalkenyl substituted oxazole compound and preparation method thereof
  • Polyfluoroalkenyl substituted oxazole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (1) 1mmol of N-acyl enamine compound (0.162 gram), 2mmol of perfluoroalkane iodide (0.692 gram), 2.5mmol of base accelerator (0.381 gram) were added into a 10mL test tube reaction tube, Add 5mL dimethyl sulfoxide to the reaction tube as a solvent, seal it tightly, and stir and react at room temperature (25° C.) for 24 hours to obtain a polyfluoroalkenyl substituted oxazole compound; wherein, the N-acyl enamine compound is N-( 1-phenylvinyl) acetamide, fluoroiodoalkane is perfluoroiodobutane; base accelerator is diazabicyclic;

[0038] (2) After the reaction in step (1) finishes, the reaction solution is successively dried through water, ethyl acetate, anhydrous sodium sulfate and separated by column chromatography (column chromatography separation condition: the stationary phase is 300~400 mesh silica gel powder, The mobile phase was ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A:B) was 1:50→1:10, and 0.315 g of reaction product 1 was ...

Embodiment 2～78

[0042] Embodiments 2-78 are basically the same as the above-mentioned embodiment 1, and the difference is as shown in the following table 1:

[0043] Table 1 Examples 2-78

[0044]

[0045]

[0046]

[0047]

Embodiment 79

[0049] (1) Add the reaction raw material formed by mixing 1mmol N-acyl enamine compound and 3mmol perfluoroalkyl iodide into 3mmol base accelerator and 5mL tetrahydrofuran solvent, and stir the reaction under air atmosphere and 90°C temperature for 24 hours, TLC detection determines the reaction process, and the reaction solution is obtained after the end of the reaction; wherein, the N-acyl enamine compound is N-(1-phenylvinyl) acetamide, and the fluoroiodoalkane is perfluoroiodobutane; the base accelerator is a diazabicyclic ring;

[0050] (2) After the reaction in step (1) finishes, the reaction solution is successively dried through water, ethyl acetate, anhydrous sodium sulfate and separated by column chromatography (column chromatography separation condition: the stationary phase is 300~400 mesh silica gel powder, The mobile phase was ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A:B) was 1:50→1:10 to obtain the reaction product.

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Abstract

The invention discloses a polyfluoroalkenyl substituted oxazole compound and a preparation method thereof. The preparation method comprises the following steps: adding a reaction raw material formed by mixing an N-acyl enamine compound and a perfluoroalkyl iodide into an alkali accelerant and a solvent, stirring and reacting for 1-24 hours in an air atmosphere at room temperature, determining a reaction process by TLC detection, obtaining a reaction solution after the reaction is finished, finally, sequentially washing, extracting and drying the reaction solution, and carrying out column chromatography separation to obtain the polyfluoroalkenyl substituted oxazole compound. According to the preparation method, the required raw materials are simple and easy to obtain, various functional group tolerance and substrate ranges are achieved, and natural products and pharmaceutical active molecular skeletons can be introduced, the preparation method disclosed by the invention is mild in reaction condition, does not need an expensive transition metal catalyst, and meets the requirements of green and economic chemistry, and according to the preparation method, a five-membered oxazole heterocyclic ring does not need to be constructed and synthesized in advance, and the highest step economy is achieved.

Description

technical field [0001] The invention belongs to the fields of organic chemistry and medicinal chemistry, and in particular relates to a polyfluoroalkenyl-substituted oxazole compound and a preparation method thereof. Background technique [0002] Due to its special structure, the oxazole ring contains both oxygen and nitrogen atoms in the five-membered ring, which exhibits unique biological activities and material properties. For example, the reported oxazole compounds have antifungal, antituberculosis, anticonvulsant, hypotensive, analgesic and anti-inflammatory activities. At present, drug molecules containing an oxazole skeleton have been used clinically, including: Linezolid (linezolid), which can be used to treat infections caused by Gram-positive (G+) cocci; Bacterial infection has a good therapeutic effect; Calyculin A (calcimycin A) protein phosphatase inhibitor can overcome clinical drug resistance and has an irreplaceable position in the treatment of infectious di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/32C07D413/04
CPCC07D263/32C07D413/04
Inventor 褚雪强沈志良葛丹华赵世文
Owner NANJING UNIV OF TECH
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