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A technology of benzoxepin and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of metal residues and not easy to obtain, and achieve the effect of easy to obtain, simple and easy method, and good adaptability
Active Publication Date: 2016-08-24
SOUTH CHINA UNIV OF TECH
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Problems solved by technology
As the reported methods all use expensive transition metal catalysts such as palladium, gold, rhodium, etc. as catalysts, it is inevitable that there will be metal residue problems in the separation, and the starting materials generally require multi-step synthesis, which is not easy to obtain.
Therefore, it is still a challenging task to develop a method for the efficient synthesis of benzoxepin compounds that is cheap and easy to obtain, easy to operate, and does not require the participation of transition metals.
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Embodiment 1
[0048] Add 0.25 mmol of o-fluorophenylacetylene, 0.35 mmol of 1-(4-chlorophenyl)-2-propanone, 0.25 mmol of potassium tert-butoxide, 1 ml of dimethyl sulfoxide in the reaction flask, and 2 Under gas protection, stir and react at 80°C for 12 hours, stop heating and stirring, cool to room temperature, and distill under reduced pressure to obtain the crude product, which is then separated and purified by column chromatography to obtain the target product. The eluent used in column chromatography is pure Hexane, 64% yield.
Embodiment 2
[0050] Add 0.25 mmol of o-fluorophenylacetylene, 0.25 mmol of 1-(4-chlorophenyl)-2-propanone, 0.25 mmol of potassium tert-butoxide, 1 ml of dimethyl sulfoxide in the reaction flask, and 2 Under gas protection, after stirring and reacting at 120°C for 12 hours, stop heating and stirring, cool to room temperature, and distill under reduced pressure to obtain the crude product, which is then separated and purified by column chromatography to obtain the target product. The eluent used in column chromatography is pure Hexane, yield 85%.
Embodiment 3
[0052] Add 0.25 mmol of o-fluorophenylacetylene, 0.25 mmol of 1-(4-chlorophenyl)-2-propanone, 0.5 mmol of potassium tert-butoxide, 1 ml of dimethyl sulfoxide in the reaction flask, and 2 Under gas protection, after stirring and reacting at 150°C for 12 hours, stop heating and stirring, cool to room temperature, and distill under reduced pressure to obtain the crude product, which is then separated and purified by column chromatography to obtain the target product. The eluent used in column chromatography is pure Hexane, yield 78%.
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Abstract
The invention relates to a synthetic method of benzo oxepin compounds. The synthetic method comprises the following steps of: with an o-fluorobenzene acetylene compound and ketone as raw materials, alkali as an accelerant and an organic solvent as a solvent, increasing temperature to 80-150 DEG C under the protection of inert gas, and stirring to react for 6-24 hours; after the reaction is finished, cooling to room temperature, carrying out reduced pressure distillation and concentration to obtain a crude product, and then purifying through column chromatography to obtain the benzo oxepin compounds. The synthetic method of the benzo oxepin compounds, which is disclosed by the invention, has the advantages of safety and easiness in operation, good adaptability to a functional group, wide adaptability to substrates and environmental friendliness and is favorable for industrial production and widely applied to medicines and organic synthesis, and the raw materials are easily available and low in price.
Description
technical field [0001] The invention relates to the technical fields of medicine and organic chemical synthesis, in particular to a method for synthesizing benzoxepin compounds. Background technique [0002] The oxa seven-membered ring skeleton widely exists in various natural products, and has good biological activity, which has attracted widespread attention. Especially the structure of benzoxepatriene is the basic structural unit of many natural products, bioactive molecules and drug molecules, and these compounds have a variety of physiological activities and can be used as antipsychotics, antidepressants, antihypertensives Drugs, anti-inflammatory drugs, etc. (R. Kiyama, T. Honma, K. Hayashi, M. Ogawa, M. Hara, M. Fujimoto and T. Fujishita, J. Med. Chem., 1995, 38, 2728–2741; Sprogoe, K.; Manniche, S.; Larsen, T.O.; Christophersen, C. Tetrahedron 2005, 61, 8718-8721; P. Kittakoop, S. Nopichai, N. Thongon, P. Charoenchai and Y. Thebtaranoth, Helv. . Acta, 2004, 87, 175...
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