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Method for visible light catalytic synthesis of 3-sulfuryl spiro-trienone compound

A technology for sulfone-based spirocyclic trienone and compound, which is applied in the field of photocatalytic synthesis of 3-sulfone-based spirocyclic trienone compound, can solve problems such as potential safety hazards, restricted application and the like, achieves simple operation, stable reaction raw materials, cleanliness energy effect

Active Publication Date: 2017-09-08
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method requires the use of equivalent potentially dangerous diiodine pentoxide and tert-butanol peroxide as oxidants, and the reaction needs to be carried out under heating (80°C). There are certain safety hazards in the reaction, which limits its application in actual production.

Method used

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  • Method for visible light catalytic synthesis of 3-sulfuryl spiro-trienone compound
  • Method for visible light catalytic synthesis of 3-sulfuryl spiro-trienone compound
  • Method for visible light catalytic synthesis of 3-sulfuryl spiro-trienone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] At room temperature, 33.1 mg of N-(4-methoxyphenyl)-N-methyl-3-phenylpropynamide and 58.5 mg of p-toluenesulfinic acid were successively added to a 15 mL reaction tube, and the photocatalyst was dissolved in water Eosin 4.3mg and acetonitrile and water (1:1) mixed solvent 2ml, mix well. Then under the irradiation of a 3w blue LED light, the reaction was stirred for 6h, and after the completion of the reaction was detected by TLC, it was concentrated under reduced pressure in a vacuum (0.08Mpa) to no solvent to obtain the crude product, and then the volume ratio was 2:1. Petroleum ether and Rinse with mixed eluents of ethyl acetate and perform flash column chromatography on a silica gel column to obtain the 3-sulfone spirotrienone product of this example as a white solid of 38.7 mg with a yield of 76%.

[0028] 1 H NMR (CDCl 3 ,500MHz,ppm):δ7.93(d,J=8.3Hz,2H),7.44(t,J=7.5Hz,1H),7.39-7.33(m,4H),7.15(d,J=7.2Hz, 2H), 6.43(s, 4H), 2.83(s, 3H), 2.44(s, 3H); 13...

Embodiment 2

[0030]

Embodiment 3

[0034]

[0035] At room temperature, 33.1 mg of N-(4-methoxyphenyl)-N-methyl-3-phenylpropynamide, 66.0 mg of p-chlorobenzenesulfinic acid, 4.3 mg, acetonitrile and water (1:1) mixed solvent 2ml, mix well. Then under the irradiation of a 3w blue LED lamp, the reaction was stirred and reacted for 10h. After the reaction was detected by TLC, it was concentrated to no solvent through vacuum (0.08Mpa) under reduced pressure to obtain the crude product, and then the volume ratio was 2:1. Petroleum ether and Rinse with mixed eluents of ethyl acetate and perform flash column chromatography on a silica gel column to obtain the 3-sulfone spirotrienone product of this example as 29.3 mg of a yellow solid with a yield of 55%.

[0036] 1 H NMR (CDCl 3 ,500MHz,ppm):δ7.99(d,J=8.7Hz,2H),7.52(d,J=8.7Hz,2H),7.46(t,J=7.5Hz,1H),7.39(t,J= 7.9Hz, 2H), 7.15(d, J=7.1Hz, 2H), 6.47-6.42(m, 4H), 2.84(s, 3H); 13 C NMR (CDCl 3 ,125MHz,ppm):δ183.0,163.4,162.4,142.0,141.3,137.5,136.4,134.5,130.8,130...

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Abstract

The invention relates to a method for visible light catalytic synthesis of a 3-sulfuryl spiro-trienone compound. The method comprises dissolving N-aryl propiolamide and sulfinic acid as raw materials in an acetonitrile / water mixed solvent, adding water soluble eosin as a photocatalyst into the solution, carrying out irradiation on the mixed solution under a 3W blue LED visible light lamp for a reaction at the room temperature for 6-24h, and after the reaction, separating and purifying the crude product to obtain the 3-sulfuryl spiro-trienone compound. The method utilizes a visible light energy source, a simple and easy available sulfinic acid as a sulfone source, cheap water soluble eosin as a photocatalyst and air as an oxidant, realizes synthesis of the 3-sulfuryl spiro-trienone compound at the room temperature, greatly reduces the energy consumption, effectively prevents the use of metal catalysts and peroxide oxidants and has good reaction safety.

Description

technical field [0001] The invention belongs to the fields of organic synthetic chemistry and medicinal chemistry, and relates to a method for photocatalytically synthesizing 3-sulfone-based spirotrienone compounds. In particular, it relates to a method for synthesizing 3-sulfone spirotrienone compound by using N-aryl propynamide catalyzed by photosensitive group water-soluble eosin and sulfinic acid to carry out sulfone group spirocyclization reaction under visible light irradiation. Background technique [0002] Spiral molecular skeletons are widely found in various natural products, drugs and functional materials. It is a synthetic cut of various complex and valuable organic compounds. In particular, azaspiro compounds have attracted extensive attention from chemists due to their unique biological activities and important synthetic applications. Therefore, a lot of work has been devoted to the synthesis of nitrogen-containing spiro compounds and their derivatives. [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/54
CPCC07D209/54
Inventor 魏伟崔环环王桦
Owner QUFU NORMAL UNIV
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