A kind of preparation method of visible light-induced 3-thiospirotrienone compound

A technology of thiospirotrienone and compounds, which is applied in the field of organic synthetic chemistry, can solve the problems of harsh reaction conditions, many by-products, and high energy consumption, and achieve the effects of mild reaction conditions, simple operation, and clean energy

Active Publication Date: 2019-09-17
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Obviously, most of the above-mentioned synthetic methods need to use metal reagents, equivalent inorganic or peroxide oxidizing agents and heating to a higher reaction temperature, the reaction conditions are harsh, energy consumption is large, and by-products are many

Method used

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  • A kind of preparation method of visible light-induced 3-thiospirotrienone compound
  • A kind of preparation method of visible light-induced 3-thiospirotrienone compound
  • A kind of preparation method of visible light-induced 3-thiospirotrienone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] At room temperature, sequentially add 33.1 mg of N-(4-methoxyphenyl)-N-methyl-3-phenylpropynylamide and 31.2 mg of p-methylthiophenol into a 15 mL reaction tube, dissolve the photocatalyst in alcohol 0.8mg of eosin and 2ml of acetonitrile were mixed uniformly, then stirred and reacted for 12h under the irradiation of a 3w blue LED lamp, and after the completion of the reaction was detected by TLC, the crude product was obtained by vacuum (0.08Mpa) concentration to no solvent, and then Rinse with a mixed eluent of petroleum ether and ethyl acetate with a volume ratio of 3:1, and perform flash column chromatography on a silica gel column to obtain the 3-thiospirotrienone product of this embodiment, which is 40.6 mg of a yellow solid. The rate is 87%.

[0026] 1 H NMR (CDCl 3 ,500MHz,ppm):δ7.31-7.28(m,1H),7.25-7.20(m,2H),7.23-7.19(m,4H),6.99(d,J=8.0Hz,2H),6.51(d ,J=10.2Hz,2H),6.45(d,J=10.3Hz,2H),2.88(s,3H),2.26(s,3H); 13 C NMR (CDCl 3 ,125MHz,ppm):δ184.0,1...

Embodiment 2

[0028]

Embodiment 3

[0032]

[0033] At room temperature, 36.9 mg of N,3-bis(4-methoxyphenyl)-N-methylphenylpropynamide, 31.2 mg of p-methylthiophenol, alcohol-soluble eosin 0.8mg, 2ml of acetonitrile solvent, mixed evenly, then stirred and reacted for 12h under the irradiation of a 3w blue LED lamp, and after the reaction was detected by TLC, it was concentrated to no solvent by vacuum (0.08Mpa) under reduced pressure to obtain a crude product, and then used Flushing with a mixed eluent of petroleum ether and ethyl acetate at a volume ratio of 2:1, followed by rapid column chromatography on a silica gel column, the 3-thiospirotrienone product of this example was obtained as 32.8 mg of a yellow oily solid, producing rate of 65%.

[0034] 1 H NMR (CDCl 3 ,500MHz,ppm):δ7.28(t,J=8.6Hz,2H),7.21(d,J=7.9Hz,2H),7.02(d,J=7.8Hz,2H),6.78(d,J= 8.6Hz, 2H), 6.51(d, J=10.2Hz, 2H), 6.48(d, J=10.2Hz, 2H), 3.78(s, 3H), 2.86(s, 3H), 2.28(s, 3H) ; 13 C NMR (CDCl 3 ,125MHz,ppm):δ184.1,167.9,160.7,152.2,145.7...

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Abstract

The invention relates to a method for preparing a visible-light-induced 3-thio spiro cyclo trienone compound, and the method comprises the following steps: dissolving raw material N-aryl propargyl amide and thiophenol (thiol) in an acetonitrile solvent, then adding photocatalyst alcohol soluble eosin, reacting for 12 hours at room temperature under a 3W blue LED visible light lamp, and separating and purifying a crude product after the termination of the reaction to obtain the 3-thio spiro cyclo trienone compound. The advantages of the method are that a cheap non-metal photosensitizer is used as a reaction catalyst, clean light energy is used as a reaction promoter, air is used as an oxidant, and the target product is constructed under mild conditions. The reaction needs no heating, no metal catalyst and dangerous peroxide oxidizing agent, the energy consumption is reduced, the metal pollution is avoided, the process condition is stable, and the reaction is safe.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry, and relates to a light-induced green preparation method of 3-thiospirotrienone compound, in particular to an N-aryl propyne catalyzed by a non-metallic photocatalyst under visible light irradiation A method for synthesizing 3-thiospirotrienone compound through thiospirocyclization reaction of amide and thiophenol (thiol). Background technique [0002] As a key structural skeleton, spirotrienones widely exist in natural products, physiologically active molecules and drug molecules. Compounds containing this type of structural skeleton have a wide range of biological activities: such as anticancer, antibacterial, anti-inflammatory, antihypertensive, etc. As shown in the following structural formula, compound A is photostephanine, which has strong antihypertensive drug activity; compound B is an efficient antioxidant agent; compound C has obvious antilipidemia activity. [0003] [00...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/50
Inventor 魏伟崔环环王桦
Owner QUFU NORMAL UNIV
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