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Method for synthesizing beta-thiocarbonyl compound by taking Bunte salt as sulfur source

A carbonyl compound and thiocarbonyl technology, applied in the field of synthesizing β-thiocarbonyl compounds, can solve the problems of waste of sulfide, easy to be oxidized, expensive, etc., and achieve the effects of economical and environmental protection, stable operation, and easy operation.

Inactive Publication Date: 2015-08-26
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, enonethioacetal is used as a raw material, and every time a molecule of target product is produced, a molecule of sulfide will be wasted. For the consideration of atom economy, the range of reaction substrates of this method is very limited.
However, mercaptans have disadvantages such as bad smell, high price, and easy to be oxidized when exposed to air, which will greatly limit their operability in scale-up production

Method used

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  • Method for synthesizing beta-thiocarbonyl compound by taking Bunte salt as sulfur source
  • Method for synthesizing beta-thiocarbonyl compound by taking Bunte salt as sulfur source
  • Method for synthesizing beta-thiocarbonyl compound by taking Bunte salt as sulfur source

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Take 1.2mmol S-benzyl (272mg), S-4-methylbenzyl (288mg), S-4-nitrobenzyl (324mg), S-allyl (212mg), S-cyclohexyl ( 348 mg) or one of the S-(2-ethoxy-2-acetyl) Bundt salts (268 mg), 1.0 mmol benzylidene acetone (146 mg) and 0.2 mmol p-toluenesulfonic acid (35 mg) were added in sequence Add 2mL of methanol to the pressure-resistant tube, and stop the reaction after 6h in an oil bath at 80°C. The reaction solvent is removed by rotary evaporation, and the pure target products 1a-1f are obtained by column chromatography on silica gel. The yields are as follows, respectively 90%, 79%, 70%, 73%, 46%, 78%.

[0025]

Embodiment 2

[0027] Take one of 1.0mmol 4'-methylchalcone (222mg), 4'-bromochalcone (286mg) or 4-methoxychalcone (238mg), 1.2mmol of S-4- Add nitrobenzyl bundt salt (324mg) and 0.2mmol p-toluenesulfonic acid (35mg) into the pressure-resistant tube in turn, add 2mL of methanol, and stop the reaction after 6h in an oil bath at 80°C, and remove the reaction solvent by rotary evaporation , through column chromatography on silica gel, the pure target product 1g-1i was obtained, and the yields were 69%, 75%, and 73%, respectively, as shown below. Among them, attached figure 1 , 2 They are the hydrogen and carbon spectra of the new compound 1i, respectively.

[0028]

Embodiment 3

[0030] Take 1.0mmol chalcone (208mg), ethyl acrylate (108μL), 4-(2-thienyl)-3-buten-2-one (152mg), N,N-dimethylacrylamide (100mg ), N-methylmaleimide (112mg), N-ethylmaleimide (126mg) or N-benzylmaleimide (188mg), 1.2mmol of S- Add benzyl bundt salt (272mg) and 0.2mmol p-toluenesulfonic acid (35mg) into the pressure-resistant tube in turn, add 2mL of methanol or dichloromethane, and stop the reaction after 6h in an oil bath at 40°C-80°C. The reaction solvent was removed by rotary evaporation, and the pure target product 1j-1p was obtained by column chromatography on silica gel. The yields were 88%, 93%, 66%, 89%, 76%, 73%, and 95%, respectively, as shown below. Among them, attached image 3 , 4 They are the hydrogen and carbon spectra of the new compound 1o, respectively.

[0031]

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Abstract

The invention discloses a method for synthesizing a beta-thiocarbonyl compound by taking Bunte salt as a sulfur source. According to the method, the Bunte salt serves as the sulfur source, a chalcone derivative or maleimide derivative serves as an electrophilic reagent, and the Bunte salt and the chalcone derivative or maleimide derivative are reacted for 6 hours under acid conditions to obtain a target product. Compared with the prior art, the method has the remarkable advantages that the Bunte salt serves as the sulfur source, is free of odor as compared with sulfur alcohol in a traditional method and can be made of low-cost sodium thiosulfate and halogenated hydrocarbon, high in yield, economical and environmentally friendly, the shape of most Bunte salt is solid powder which is easily operated, the reaction does not need transition metal serving as a catalyst, and environmental pollution caused by the reaction is reduced.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing β-thiocarbonyl compounds by using bundt salt as a sulfur source. Background technique [0002] In the past few decades, sulfur-containing compounds have received extensive attention due to their potential applications in new drugs, pesticides, chemical reagents, and materials science. Among them, the synthesis of β-thiocarbonyl compounds by 1,4-Michael addition is one of the important ways to construct sulfur-containing compounds. [0003] The synthetic method of the reported β-thiocarbonyl compound roughly has the following several kinds: (1) Abaee et al. Alcohol is used as raw material, water is used as solvent, and β-thiocarbonyl compound is obtained through aldol condensation-Michael addition in the presence of diethylamine. Sharma et al. (Tetrahedron Letters, 49(27), 4272-4275; 2008) used silica adsorbed by fluoroboric acid as a cataly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/22C07C323/52C07C319/14C07D207/416C07D333/22
Inventor 陆国平林雅玫
Owner NANJING UNIV OF SCI & TECH
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