Preparation method of chiral spiro naphthoquinone benzopyran hydroxyindole compound

A pyranoxindole compound and a compound technology are applied in the field of preparation of chiral spironaphthoquinopyranoxidole compounds, and can solve the problems of narrow substrate application range, harsh reaction conditions, narrow substrate range and the like, Achieve excellent enantioselectivity, mild reaction conditions, and a wide range of substrates
CN103554117AInactive Publication Date: 2014-02-05SUZHOU UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
SUZHOU UNIV
Publication Date
2014-02-05
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention discloses a preparation method of a chiral spiro naphthoquinone benzopyran hydroxyindole compound. The method comprises the following specific steps: reacting the condensation product of an isatin compound and propane dinitrile and a 2-hydroxyl-1,4-naphthoquinone compound in a solvent under the catalysis of quinine thiourea dihydride, thereby obtaining a product. According to the method, raw materials are simple and easily available, the reaction condition is mild, the post-treatment is simple and convenient, the applicative substrates are wide, the enantioselectivity is high, and the yield can reach 99%; therefore, the method is a novel method capable of efficiently synthesizing the chiral spiro naphthoquinone benzopyran hydroxyindole compound having important medicinal value and asymmetric synthesis value. The compound prepared by the method can be used for preparing intermediates of chiral drugs and has wide physiological and pharmacological activities.
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Description

technical field

[0001] The invention relates to the preparation of naphthoquinopyran organic compounds, in particular to a preparation method of chiral spironaphthoquinopyran oxindole compounds. Background technique

[0002] Naphthoquinone structural compounds have been found to have broad-spectrum antibacterial and anticancer activities, and are the core fragments of many natural products and modern drugs, such as α -lapachone, β - Lappaquinone, metamycin, etc., are widely used in the treatment of various diseases. Indolinone is a nitrogen-containing aromatic heterocyclic organic compound with a bicyclic structure consisting of a benzene ring and a five-membered nitrogen heterocycle. It is an important pharmaceutical and pesticide intermediate. Indol-2-one derivatives are widely used as pharmacophore in medicine. The spironaphthoquinonepyranoxindole compound contains naphthoquinone, pyran and oxindole structural units, and is of great significance as a medicinal compound...

Claims

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