Preparation method of fluoro-3,4-dihydroisocoumarin derivative

Abstract

The invention discloses a preparation method of a fluoro-3,4-dihydroisocoumarin derivative (I), and belongs to the field of organic chemistry. According to the method, under the assistance of microwaves, substituted o-vinylphenol benzoic acid and Selectfluor fluoride agents are used as raw materials to take a reaction in a solvent to synthesize a fluoro-3,4-dihydroisocoumarin derivative. The formula (I) is shown as the accompanying drawing. Compared with the existing synthesis method, the method provided by the invention has the following advantages that (1) raw materials are cheap and can be easily obtained; the fluoro-3,4-dihydroisocoumarin derivative is synthesized in one step; the cost is low; good application prospects are realized; (2) the reaction conditions are mild; the reaction is performed under the air condition; the yield is high; the operation is convenient; green and environment-friendly effects are achieved; the industrial production is facilitated. A novel path is provided for the synthesis of the fluoro-3,4-dihydroisocoumarin derivative.

Description

technical field [0001] The invention relates to a preparation method of fluoro-3,4-dihydrocoumarin derivatives, belonging to the field of organic synthesis. Background technique [0002] Isocoumarin is the basic structure of some natural products and widely exists in nature. Its derivatives have a wide range of physiological and biological activities, such as antibacterial, anti-inflammatory, anticancer, protease inhibitory and anticancer activities. 3,4‐Dihydroisocoumarins are secondary metabolites of fungi, molds, bacteria, higher plants and animals. 3,4‐dihydroisocoumarin containing halogen has antibacterial, antifungal effects, and can act as a serine protease inhibitor and an inhibitor of human Q31 granule lytic enzyme A. Chlorine and bromine-containing 3,4-dihydroisocoumarin have been reported, but there are few reports on the synthesis of fluorine-containing 3,4-dihydroisocoumarin derivatives. Due to the unique physical properties and biological activities of fluoro...

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Problems solved by technology

(2) Using methyl o-vinylbenzoate and pyridine hydrofluoride as raw materials, m-chloroperoxybenzoic acid as an oxidant, under the catalysis of a chiral catalyst, react at -50°C for 24 hours to obtain fluoro-3 , 4‐dihydroisocoumarin derivatives (Woerly EM, Banik SM, JacobsenEN, J.Am.Chem.Soc., 2016,138,13858‐13861); this method requires relatively harsh reaction conditions, long reaction time, catalyst Relatively expensive, and the scope of application of the substrate is limited

[0004] It can be seen from the above that traditional synthetic methods generally require the addition of strong acids or catalysts to catalyze the reaction. The price of the substrate or catalyst is relatively expensive, the reaction conditions are relatively harsh, the reaction time is long, and the scope of application of the substrate is limited.

For large-scale industrial production, it often requires equipment with high corrosion resistance, and from the perspective of environmental protection, it is not very ideal

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