Method for synthesizing polysubstituted dihydrofuran

A technology of dihydrofuran and synthesis method, which is applied in the field of preparation of multi-substituted dihydrofuran, can solve problems such as low utilization rate of atoms, complex operation conditions, expensive metal catalysts, etc., and achieve cheap and environmentally friendly reagents, high atom economy, Good substrate adaptability
CN109810079AInactive Publication Date: 2019-05-28ZHEJIANG UNIV OF TECH
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
ZHEJIANG UNIV OF TECH
Publication Date
2019-05-28
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention discloses a novel method for synthesizing a polysubstituted dihydrofuran compound. The method for synthesizing the polysubstituted dihydrofuran compound comprises the following steps that an olefinic dicarbonyl compound shown in the formula (I), an iodine source and an oxidizing agent are mixed in a solvent, after reacting is performed at the room temperature for 8-12 h, a reaction solution is subjected to post-treatment to obtain a dihydrofuran compound shown in the formula (II); the ratio of the amount of feeding materials of the olefinic dicarbonyl compound shown in the formula (I) to the iodine source to the oxidizing agent is 1 to 0.5-1.1-2.5; and the oxidizing agent is tert-butyl hydroperoxide or hydrogen peroxide. The method for synthesizing the polysubstituted dihydrofuran compound directly uses the olefinic dicarbonyl compound as a raw material to carry out an intramolecular cyclization reaction; the whole process does not require a metal catalyst, the metal residue is avoided, the reaction operation is simple, the reaction can be carried out under mild conditions, a good yield is obtained, and the application of the polysubstituted dihydrofuran compound in pharmaceutical synthesis is further facilitated. (Please see the specification for the formulae).
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Description

(1) Technical field

[0001] The present invention relates to a kind of I 2 / TBHP-mediated preparation of polysubstituted dihydrofurans. (2) Background technology

[0002] Dihydrofuran compound is a very important biological structural unit, which widely exists in natural products and drug molecules, and the multi-substituted 2,3-dihydrofuran compound can be used as a synthetic building block of many complex heterocyclic compounds.

[0003] For example, the dihydrofuran derivative Clerodin is a chemical component extracted from the natural neem growing in India. They have insect repellent activity and can effectively kill a variety of pests. Another example is the compound nepetaefolin extracted from the lip plant Leonotis nepetaefolia in the Caribbean. , it has strong anti-cancer and anti-tumor activity. Although there are some reports on the synthetic methods of this class of compounds, the synthetic methods of the reported documents either use expensive metal catalysts, o...

Claims

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