Synthesis of isoflavone compound through Stille crossed coupling reaction

A technology for isoflavones and bromoisoflavones, which is applied to isoflavone compounds and related medicines and their application fields, can solve the problems of large influence on catalyst and solvent yield, low industrial application value, complicated reaction process and the like, and achieves low production cost. , the effect of mild reaction conditions and simple equipment

Inactive Publication Date: 2011-11-16
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 ro

Method used

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  • Synthesis of isoflavone compound through Stille crossed coupling reaction
  • Synthesis of isoflavone compound through Stille crossed coupling reaction
  • Synthesis of isoflavone compound through Stille crossed coupling reaction

Examples

Experimental program
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Effect test

Embodiment 1

[0046] In this example, 3-iodochromanone and ethanol with 25 times the weight of 3-iodochromanone are added to the reaction kettle as a solvent, and after stirring evenly, add 3-iodochromanone with a molar ratio of 4:1.1 Tetraphenyltin and 10% palladium carbon with a molar ratio of 1:0.1 to chromone and sodium acetate with a molar ratio of 1:2 to 3-iodochromone, and the temperature of the reaction solution is 80° C. Make it reflux reaction, stop the reaction after 1 hour, pour an appropriate amount of column chromatography silica gel into the reaction solution after the reaction solution is cooled to room temperature, distill under reduced pressure to recover the solvent, use petroleum ether and ethyl acetate mixed solvent as eluent to pass through silica gel The pure isoflavones were separated by column chromatography gradient elution.

[0047] Adopt this example to prepare compound (1) isoflavones, after testing its physical and chemical properties are as follows:

[0048] ...

Embodiment 2

[0055] In this example, 6,8-dibromo-3-iodochromanone, 6-bromo-3-iodochromanone, 6-fluoro-3-iodochromanone, 7-methyl Oxygen-3-iodine, and acetonitrile with 20 times the weight of the corresponding chromone as a solvent, after stirring evenly, add tetraphenyltin with a mol ratio of 4: 1.3 and a chromone molar ratio of 1 : Palladium nitrate of 0.005 and sodium bicarbonate with a molar ratio of 1:4 to chromone, use a temperature regulating device to make the temperature of the reaction solution 60°C to reflux the reaction, stop after 5 hours of reaction, and cool the reaction solution to room temperature An appropriate amount of column chromatography silica gel was poured into the reaction solution, the solvent was recovered by distillation under reduced pressure, and the mixed solvent of petroleum ether and ethyl acetate was used as the eluent to separate the compounds (2) 6, 8- Dibromoisoflavone, compound (3) 6-bromoisoflavone, compound (4) 6-fluoroisoflavone, compound (5) pure ...

Embodiment 3

[0085] In this example, 3-iodochromanone, 6,8-dibromo-3-iodochromanone, 6-bromo-3-iodochromanone, 6-fluoro-3-iodochrome Proketone, 7-methoxyl-3-iodochromanone, and DMF of 10 times the weight of the corresponding chromone as a solvent, after stirring evenly, add p-methyltetraphenylene with a molar ratio of 4:1.2 to chromone base tin and tetrakis(triphenylphosphine) palladium with a molar ratio of 1:0.06 to chromone and sodium carbonate with a molar ratio of 1:8 to chromone, the temperature of the reaction solution is 100° C. Its reflux reaction, stop after 3 hours of reaction, pour an appropriate amount of column chromatography silica gel into the concentrated reaction solution to recover the solvent by distillation under reduced pressure, use petroleum ether and ethyl acetate mixed solvent as eluent, and perform gradient elution through silica gel column chromatography Separate and obtain compound (6) 4'-methyl isoflavone, compound (7) 6,8-dibromo-4'-methyl isoflavone, compoun...

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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...

Claims

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Application Information

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IPC IPC(8): C07D311/36C07D407/04A61K31/352A61P35/00A61P25/28A61P25/16A61P21/00A61P9/10A61P9/12A61P5/00A61P5/26A61P19/10A61P15/12A61P39/06A61P25/22A61P25/24
Inventor 张尊听梁博薛东刘谦光李午戊杨君玲
Owner SHAANXI NORMAL UNIV
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