Pyran compound and synthesis method thereof

A synthesis method and compound technology, applied in the field of pyran compounds and their synthesis, can solve problems such as hindering the application of schemes, long reaction time, metal catalysts and high reaction temperature, and achieve excellent inhibitory activity, high application value and product yield high effect

Active Publication Date: 2021-07-23
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, despite the many advantages of these existing methods mentioned above, there are still some limitations, including long reaction times, metal catalysts, and high reaction temperatures, and hinder the application of these protocols.

Method used

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  • Pyran compound and synthesis method thereof
  • Pyran compound and synthesis method thereof
  • Pyran compound and synthesis method thereof

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Embodiment Construction

[0053] The technical solutions of the present invention will be further described below in conjunction with the embodiments. Obviously, the described embodiments are only some of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making creative efforts belong to the protection scope of the present invention.

[0054] The invention provides a synthetic method of pyran compounds, specifically: through propargyl p-benzoquinone methides ((aza)-p-QMs), and 4-hydroxycoumarin and its derivatives or 1 , 3-diketone compounds are prepared by (3+3) cycloaddition reaction, the specific reaction formula is as follows:

[0055]

[0056] The method provided by the present invention can efficiently and rapidly synthesize a series of pyran compounds with rich functional groups and novel structures under relatively mild conditions. According to the research on the i...

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Abstract

The invention discloses a pyran compound and a synthesis method thereof. The pyran compound has a structural formula (1) or (2). The pyran compound is synthesized from propargyl p-benzoquinone methylate, 4-hydroxycoumarin and a derivative thereof or a 1, 3-diketone compound at room temperature. According to the synthesis method, the pyran compound can be efficiently synthesized under a mild condition, the product yield reaches up to 99%, the pyran compound shows excellent inhibitory activity on alpha-glucosidase, the 3 + 3 cyclization initiated by 1, 8-conjugate addition of the 4-hydroxycoumarin and the 1, 3-dicarbonyl compound and propargyl (aza)-p-quinone methylate generated in situ under the catalysis of Bronsted acid is realized, and the application value is high.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a pyran compound and a synthesis method thereof. Background technique [0002] Pyranocoumarin is an oxygen-containing cyclic compound widely distributed in natural products and medicines, including Bothrioclinin, Ferprenin, Cyclocoumarol and Ethuliacoumarin A, and its structural formula is as follows: [0003] [0004] In the prior art, pyranocoumarins are usually prepared by the cyclization reaction of 4-hydroxycoumarin with α, β-unsaturated aldehydes / ketones and nitroalkenes. These methods mainly involve the cycloaddition induced by Michael addition reaction. Another important synthetic method of pyranocoumarin is the cyclization of 4-hydroxycoumarin with propargyl alcohol. However, despite the many advantages of these existing methods mentioned above, there are still some limitations, including long reaction times, high metal catalysts, and high rea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04C07D495/04C07D491/052C07D311/74C07D311/94
CPCC07D493/04C07D495/04C07D491/052C07D311/74C07D311/94
Inventor 张祥志潘汉鹏邱宗旺李保琼朱志强刘宏福吴惠盈钟紫婷曹叔铭
Owner WUYI UNIV
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