Synthetic method of (E)-alkenyl sulfone compounds

A synthetic method and compound technology, applied in the preparation of organic compounds, organic chemical methods, chemical instruments and methods, etc., to achieve the effects of simple synthetic routes, mild reaction conditions, and improved yield and purity

Inactive Publication Date: 2018-12-28
HUNAN UNIV OF ARTS & SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although some research progress has been made in this field, these methods require the u...

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  • Synthetic method of (E)-alkenyl sulfone compounds
  • Synthetic method of (E)-alkenyl sulfone compounds
  • Synthetic method of (E)-alkenyl sulfone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041]

[0042] (1) Step 1: Add benzaldehyde (8.8g, 7.8mmol) and nitromethane (4.3g, 7.7mmol) to methanol (15mL), cool to -5°C, stir for half an hour, then slowly add sodium hydroxide solution (15 mL), methanol (15 mL) was added, and the reaction was continued for 1 hour after the dropwise addition was completed. Add crushed ice to the reaction solution, pour it into 4mol / L hydrochloric acid (75mL) after 5min, precipitate a light yellow precipitate, filter, wash with water (30mL×3), transfer the solid to a flask, recrystallize from ethanol, and dry at room temperature 7.9 g of β-nitrostyrene solid was obtained, with a yield of 71%.

[0043] (2) Step 2: The above-mentioned β-nitrostyrene (74.5mg, 0.5mmol), p-toluenesulfonyl hydrazide (186mg, 1.0mmol), tetrabutylammonium iodide (36.5mg, 0.1mmol) and Potassium persulfate (270.0 mg, 1.0 mmol) was added into the flask, and the mixture was reacted at 80° C. for 8 hours. After the reaction was detected by TLC, it was separated...

Embodiment 2

[0046]

[0047] (1) Step 1: Mix p-tolualdehyde (3.48g, 29mmol), ammonium acetate (1.3g, 1.7mmol), acetic acid (7.5mL), and nitromethane (2g, 33mmol), heat and reflux for four hours, The reaction solution was cooled to room temperature, poured into ice water (25mL), precipitated, stirred, filtered, washed with water (30mL×3), and the crude product was recrystallized with ethanol to obtain the product β-p-methylnitrostyrene as a solid (3.3 g), 72% yield.

[0048] (2) Step 2: Mix the above β-p-methylnitrostyrene (81.5mg, 0.5mmol), p-toluenesulfonyl hydrazide (93mg, 0.5mmol), tetrabutylammonium iodide (91.3mg, 0.25 mmol) and potassium persulfate (135 mg, 0.5 mmol) were added into the flask, and the mixture was reacted at 80° C. for 8 hours. After TLC detection reaction finishes, use column chromatography (eluent: sherwood oil / ethyl acetate volume ratio 9:1) to separate and obtain 1-(4-methylphenyl)-2-p-toluenesulfonyl olefin ( Compound 2) 85.7 mg, yield 63%.

[0049] Produ...

Embodiment 3

[0051]

[0052] (1) Step 1: Mix p-chlorobenzaldehyde (4.06g, 29mmol), ammonium acetate (1.3g, 1.7mmol), acetic acid (7.5mL), and nitromethane (2g, 33mmol), heat and reflux for four hours, and The reaction solution was cooled to room temperature, poured into ice water (25mL), precipitated, stirred, filtered, washed with water (30mL×3), and the crude product was recrystallized with ethanol to obtain the product β-p-chloronitrostyrene solid (4.3 g), yield 80%.

[0053] (2) Step 2: The above-mentioned β-p-chloronitrostyrene (91.5mg, 0.5mmol), p-toluenesulfonyl hydrazide (930mg, 5.0mmol), tetrabutylammonium iodide (182.5mg, 0.5mmol) ) and ammonium persulfate (570 mg, 2.5 mmol) were added into the flask, and the mixture was reacted at 80° C. for 8 hours. After the TLC detection reaction finishes, use column chromatography (eluent: petroleum ether / ethyl acetate volume ratio 9:1) to separate and obtain 1-(4-chlorophenyl)-2-p-toluenesulfonyl alkene (compound 3) 58.4 mg, yield 40...

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Abstract

The invention discloses a synthetic method of (E)-alkenyl sulfone compounds. The method comprises the following steps: beta-nitroolefin compounds shown as formula I in the description, sulfohydrazidecompounds shown as formula II in the description, an iodine-containing nonmetal catalyst and a peroxide oxidizing agent are mixed for a reaction, and a mixture obtained after the reaction is subjectedto postprocessing, and the (E)-alkenyl sulfone compounds shown as formula III in the description are obtained. Beta-nitroolefin compounds, the sulfohydrazide compounds, the iodine-containing nonmetalcatalyst and the peroxide oxidizing agent are taken as main raw materials, the corresponding (E)-alkenyl sulfone compounds are synthesized through free radical reaction, the iodine-containing nonmetal catalyst iodine or tetrabutylammonium iodide is used, the raw materials are simple, easily available, cheap, non-toxic and pollution-free to the environment, the dosage of the catalyst is small, thecatalyst has higher specificity for the reaction, synthetic reaction time can be shortened, the problem that the metal catalyst is difficult to separate in the prior art can be well solved, postprocessing difficulty is reduced, yield of the final product is increased, and purity of the final product is improved.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of (E)-alkenyl sulfone compounds. Background technique [0002] Alkenyl sulfone compounds can be used as reactants or intermediates in many organic synthesis reactions. They are good Michael acceptors and can easily participate in cycloaddition reactions. At the same time, many compounds with vinyl sulfone structures have certain biological activities or participate in the synthesis of compounds with pharmaceutical activity. For example, compounds with vinyl sulfone structures can be used as inhibitors of certain proteases, inhibitors of HIV-1 integrase, or can inhibit cell proliferation and the like. Therefore, this type of compound has a wide range of applications in the fields of biology and medicine. The synthesis method of vinyl sulfone compounds has been one of the research hotspots in the field of organic synthesis in recent years...

Claims

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Application Information

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IPC IPC(8): C07C315/00C07C317/14C07C317/22C07D333/18C07C201/12C07C205/04
CPCC07B2200/09C07C201/12C07C315/00C07D333/18C07C317/14C07C317/22C07C205/04
Inventor 唐裕才左成钢张向阳
Owner HUNAN UNIV OF ARTS & SCI
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