Synthesis of isoflavone compound through Stille crossed coupling reaction

Abstract

The invention belongs to heterocyclic compound technical field, concretely relating to a heterocyclic compound in which unhydrogenated six-member heterocyclic ring containing an only ring hetero atom of an oxygen atom fuses with other phenyl rings. The invention provides a synthetic method of an isoflavone compound. The method comprises the steps of adding a reactant (substituted) 3-iodine chromone and tetraarylated tin into a solvent for a chemical reaction, and using column chromatography and recrystallization methods to purify the above resultant to obtain the pure compound of the present invention. By using the method, medicinal isoflavone such as daidzein, genistein, Ipriflavone, puerarin, formononetin and the like is prepared, and a new technical route of industrialization production of the above medicaments is established. Simultaneously, a series of novel isoflavone compounds with potential physiological activity are prepared.

Description

technical field [0001] The invention belongs to the technical field of heterocyclic compounds, and specifically relates to a heterocyclic compound containing a six-membered ring without hydrogenation, which has an oxygen atom as the only ring heteroatom and is fused with other rings. The present invention relates to formulations, beverages, food products, methods and therapeutic applications relating to, comprising, containing, including and / or preparing certain isoflavone compounds. Specifically, the present invention relates to isoflavone compounds and related medicines and applications thereof. Background technique [0002] Isoflavones are phenolic compounds based on benzochromone rings formed by cyclization of cinnamoyl-CoA side chains during the metabolism of phenylalanine in plants. The 3-phenyl derivatives are isoflavones, which belong to plants secondary metabolites. Modern pharmacological studies have shown that isoflavones play a role in the cardiovascular system...

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Problems solved by technology

Ib Thomsen etc. have also reported that isoflavones are synthesized by reacting salicylaldoxime and enamine (N-styrylmarin), and can obtain isoflavones through acetylation, reduction, and ring closure reactions, and the yield is 37%. The reaction process Complex, low yield and separation and purification by thin-layer chromatography, so the industrial application value is low

[0008] In the 1970s, the synthesis of isoflavones by the chalcone route appeared, mainly using substituted acetophenones and substituted benzaldehydes as raw materials, which were condensed by Claisen-Schemidt to generate corresponding chalcones. The role of chalcones in heavy metal thallium salts Under the following conditions, the rearrangement reaction is used to synthesize isoflavones, which has a low yield and a large amount of toxic thallium salts are used in the production process; it is further improved to prepare isoflavones by oxidative rearrangement of chalcones, but the yield is low

The oxidative rearrangement of flavanones to prepare isoflavones is also one of the methods for preparing isoflavones. Most of them use thallium salts and periodides as catalysts to catalyze the reaction, but catalysts and solvents have a great influence on the yield of the reaction.

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