2-(2,4,6-trimethylbenzeneseleno)-5-methylbenzoxazole compound and preparation method thereof

A technology of methylbenzoxazole and trimethylbenzene, which is applied in the field of organic compound synthesis, can solve the problems of increased synthesis cost, environmental pollution, and large quantities, and achieves the effects of simple operation, simple post-processing operation, and high reaction efficiency

Active Publication Date: 2018-09-04
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In 2012, VG ​​Ricordi et al. (Glycerol as a Recyclable Solvent for Copper-Catalyzed Cross-Coupling Reactions of Diaryl Diselenides with Aryl Boronic Acids.Green Chem.2012, 14, 1030-1034.) reported cuprous iodide catalyzed aryl boronic acid and diaryl boronic acid The aryl diselenide compound is obtained under the condition of a strong polar solvent DMSO to obtain an asymmetric diaryl selenide compound. The defect is that the reaction needs to prepare aryl boron reagent and diaryl diselenide in advance, which increases the synthesis cost. The reaction formula

Method used

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  • 2-(2,4,6-trimethylbenzeneseleno)-5-methylbenzoxazole compound and preparation method thereof
  • 2-(2,4,6-trimethylbenzeneseleno)-5-methylbenzoxazole compound and preparation method thereof
  • 2-(2,4,6-trimethylbenzeneseleno)-5-methylbenzoxazole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Synthesis of 2-(2,4,6-trimethylphenylselenyl)-5-methylbenzoxazole

[0050]

[0051] At room temperature, 2,4,6-trimethyliodobenzene (1.2mmol, 3equiv), elemental selenium (1.2mmol, 3equiv), 5-methylbenzoxazole (0.4mmol, 1equiv), Cu(OAc ) 2 (0.04mmol), ammonium bicarbonate (1.2mmol, 3equiv) were added to the reaction tube, then filled with nitrogen, and replaced three times, under the nitrogen reaction environment, then added 2mL DMF reaction solvent, stirred at 140 ° C reaction temperature for 24h . After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then diluted with ethyl acetate, the diluted solution was transferred to a separatory funnel, extracted with saturated brine, the aqueous phase and the organic phase were separated, and then diluted with acetic acid Extract the aqueous phase 3 times with ethyl ether, combine the organic phases, add 5g of anhydrous sodium sulfate, stand still for 30min, wash the filt...

Embodiment 2

[0058] Scaled-up Synthesis of 2-(2,4,6-Trimethylphenylselenyl)-5-methylbenzoxazole

[0059]

[0060] At room temperature, 2,4,6-trimethyliodobenzene (12mmol, 3equiv), elemental selenium (12mmol, 3equiv), 5-methylbenzoxazole (4mmol, 1equiv), Cu(OAc) 2 (0.4mmol), ammonium bicarbonate (12mmol, 3equiv) were added to the reaction tube, then filled with nitrogen, and replaced three times, under nitrogen reaction environment, then added 20mL DMF reaction solvent, stirred at 140 ° C reaction temperature for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then diluted with ethyl acetate, the diluted solution was transferred to a separatory funnel, extracted with saturated brine, the aqueous phase and the organic phase were separated, and then diluted with acetic acid Extract the aqueous phase 3 times with ethyl ester, combine the organic phases, add 25g of anhydrous sodium sulfate, stand still for 30min, wash the filter...

Embodiment 3-14

[0063] Except that the catalyzer copper acetate therein is replaced by the following copper catalyst respectively, in the same manner as Example 1 with the highest product yield, embodiments 3-14 have been implemented respectively, the yield of the copper compound used and the corresponding product As shown in Table 1 below.

[0064] Table 1

[0065]

[0066]

[0067] As can be seen from Table 1 above, when other copper compounds are used, the product yields are greatly reduced. This proves that the catalyst copper acetate used in the present invention has efficient catalytic performance for this reaction.

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Abstract

The invention relates to a 2-(2,4,6-trimethylbenzeneseleno)-5-methylbenzoxazole compound and a preparation method thereof. The preparation method comprises the following steps: with 5-methylbenzoxazole and 2,4,6-trimethylphenyl iodide as reactive raw materials in an organic solvent, and elemental selenium as a selenide reagent, carrying out a cascade reaction under the jointed promotion effect ofa copper catalyst and alkali, thereby obtaining the 2-(2,4,6-trimethylbenzeneseleno)-5-methylbenzoxazole compound. The method is simple in reaction conditions, the product is high in yield and purity,a novel synthetic route and method can be developed for the 2-(2,4,6-trimethylbenzeneseleno)-5-methylbenzoxazole compound, and the compound has excellent application potential and research value.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a 2-(2,4,6-trimethylphenylselenyl)-5-methylbenzoxazole compound and a preparation method thereof. Background technique [0002] Selenium has anti-cancer, anti-oxidation, enhances human immunity, antagonizes harmful heavy metals, regulates vitamin absorption, regulates protein synthesis in the human body, and enhances reproductive function. It is also an important component of peroxidase in muscles and seminal plasma. It is recognized by scientists It is called the "king of anti-cancer" of human trace elements. [0003] So far, people have developed a number of drug molecules containing selenoether structures in many specific application fields such as medicine and chemical engineering: Ebselen (Ebselen) is a new type of anti-inflammatory drug developed by Japan's Daiichi Pharmaceutical and Germany's Nattermann, Currently in phase III clinical resea...

Claims

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Application Information

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IPC IPC(8): C07D263/58
CPCC07D263/58
Inventor 吴戈
Owner WENZHOU MEDICAL UNIV
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