Photochemical reaction synthesis for isoflavones

Abstract

The invention belongs to the technical field of heterocyclic compounds, and particularly relates to a heterocyclic compound with an unhydrogenated heterocycle, a six-membered cycle, and an oxygen atom used as the only heterocyclic atom for being fused with other cycles. The invention provides a novel method for photochemical reaction synthesis for isoflavones. The process of the novel method comprises the following steps of: adding (substituted) 3-(dimethylamino)-1-(2-hydroxylphenyl) propyl-2-alkene-1-ketone, substituted aromatic hydrocarbon and iodine elementary substance in a solvent; reacting under ultraviolet irradiation; performing reduced pressure distillation to recover the solvent after the reaction; and obtaining the compounds disclosed by the invention, namely, isoflavone pure products, via column chromatography separation and purification. The medicinal isoflavones of ipriflavone, formononetin, isoflavoues aglycone, genistein, puerarin and the like are prepared by applying the method, a new technical route is provided for industrialized production for the medicines aforementioned, and a series of novel isoflavone compounds with potential physiological activity are prepared simultaneously.

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. 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, endocrine system, central nervous system, immune system and anti-tumor, anti-oxidation and free radical scavenging effects, estrogen-like effects, anti-inflammatory and anti-allergic effects, antibacterial and antiviral effects etc. have obvious pharmacological effects. For example, formononetin that can prevent and ...

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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

[0007] 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. The yield of this method is low and a large amount of toxic thallium salts are used in the production process; and the improved method for preparing isoflavones through oxidative rearrangement of chalcones has a low yield.

Isoflavones are synthesized by Still coupling reaction, although the yield is high, but toxic organotin reagents are used, and noble metal catalysts are also required

In 2012, Knochel et al. synthesized isoflavones through Negishi coupling reaction. The reaction conditions are mild, but the preparation of organozinc reagents is difficult, the operation is complicated, and inert gas protection is required, which limits its large-scale industrial production.

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