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A kind of synthetic method of aryl selenium heterocyclic compound

A technology of heterocyclic compounds and compounds, which is applied in the field of organic compound synthesis, can solve the problems of complex operation and poor functional group tolerance of aryl selenium heterocyclic compounds, and achieve the effect of simple post-processing operation, simple operation and simple post-processing

Inactive Publication Date: 2019-08-20
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] The first technical problem to be solved by the present invention is the problem of complicated operation in the preparation process of aryl selenium heterocyclic compound
[0016] The second technical problem to be solved by the present invention is the poor tolerance of functional groups in the preparation process of aryl selenium heterocyclic compounds
[0017] The third technical problem to be solved by the present invention is the problem that the preparation process of aryl selenium heterocyclic compound is suitable for large-scale industrial production

Method used

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  • A kind of synthetic method of aryl selenium heterocyclic compound
  • A kind of synthetic method of aryl selenium heterocyclic compound
  • A kind of synthetic method of aryl selenium heterocyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Synthesis of 2,6-Diphenylselenylpyridine Nitride Oxide

[0064]

[0065] At room temperature, pyridine nitroxide-2-carboxylic acid (0.4mmol, 1equiv), diphenyldiselenide (0.8mmol, 2equiv), Cu(OAc) 2 (0.06mmol), 1,10-phenanthroline (0.06mmol), potassium carbonate (1.2mmol, 3equiv) and 2mL toluene join in the reaction tube, fill with oxygen then, and replace three times, under oxygen reaction environment, Stir at 150°C reaction temperature for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then ethyl acetate was added to filter, then the solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ether=98: 2), and the product was Yellow liquid, yield 58%, product weight 94mg.

[0066] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0067] 1 H NMR (500MHz, CDCl 3 ): δ7.72(d, J=7.3Hz, 4H), 7.51-7.48(m, 2H), 7.45-7....

Embodiment 2

[0074] Synthesis of 3-methyl-2-phenylselenylbenzothiophene

[0075]

[0076] At room temperature, 3-methyl-benzothiophene-2-carboxylic acid (0.4mmol, 1equiv), diphenyldiselenide (0.8mmol, 2equiv), Cu(OAc) 2 (0.06mmol), 1,10-phenanthroline (0.06mmol), potassium carbonate (1.2mmol, 3equiv) and 2mL toluene join in the reaction tube, fill with oxygen then, and replace three times, under oxygen reaction environment, Stir at 150°C reaction temperature for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then ethyl acetate was added to filter, then the solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ether=98: 2), and the product was Yellow liquid, yield 76%, product weight 92mg.

[0077] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0078] 1 H NMR (500MHz, CDCl 3 ): δ7.53(d, J=7.6Hz, 1H), 7.45(d, J=8.1Hz, 1H), 7...

Embodiment 3

[0085] Synthesis of 3-methyl-2-phenylselenylbenzofuran

[0086]

[0087] At room temperature, 3-methyl-benzofuran-2-carboxylic acid (0.4mmol, 1equiv), diphenyldiselenide (0.8mmol, 2equiv), Cu(OAc) 2 (0.06mmol), 1,10-phenanthroline (0.06mmol), potassium carbonate (1.2mmol, 3equiv) and 2mL toluene join in the reaction tube, fill with oxygen then, and replace three times, under oxygen reaction environment, Stir at 150°C reaction temperature for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then ethyl acetate was added to filter, then the solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ether=98: 2), and the product was Yellow liquid, yield 80%, product weight 92mg.

[0088] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0089] 1 H NMR (500MHz, CDCl 3 ): δ7.52(d, J=7.7Hz, 1H), 7.45(d, J=8.2Hz, 1H), 7.35-7.33...

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Abstract

The invention relates to a method for synthesizing an arylseleno-heterocyclic compound. The method comprises the following step: in an organic solvent, under an oxygen condition, by taking heterocyclic aromatic carboxylic acid and diaryl diselenide ether as reaction raw materials, and under the cooperative promotion action of a copper catalyst, a ligand and alkali, performing oxidative decarboxylation coupling reaction, thereby obtaining the arylseleno-heterocyclic compound. By adopting the method, the substrate, namely the heterocyclic aromatic carboxylic acid, and the copper catalyst are cheap and easy to obtain, the substrate range is wide, reaction conditions are simple, the yield and the purity of the product are high, novel synthesis routes and methods are developed for arylseleno-heterocyclic compounds, and the method has good application potentials and study values.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of an aromatic selenium heterocyclic compound. Background technique [0002] So far, selenium has been widely used in the synthesis of medicine, polymer materials, and pesticides. For example, a number of drug molecules containing selenoether structures have been developed: Ebselen (Ebselen) was developed by Daiichi Pharmaceutical in Japan and Nattermann in Germany. A new type of anti-inflammatory drug, which is currently in clinical phase III research; selenium-containing tegafur phosphorothioate compounds with anti-tumor activity, selenium-modified southern Radix Radix polysaccharide compounds that have inhibitory effects on a variety of tumor cell lines . Even in the field of agriculture, the structure of selenide ether compounds exists in a wide spectrum of fungicides and herbicides, such as selenium-containing triazole amide...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/89C07D333/62C07D307/82C07D277/32
Inventor 吴戈王静
Owner WENZHOU MEDICAL UNIV
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