Synthesis method and application of a kind of visible light-promoted dithiocarbamate compound

A technology for dithiocarbamic acid and ester compounds, which is applied in the field of photocatalytic organic synthesis, can solve the problems of inability to meet the screening requirements of active lead compounds, complicated reaction steps, limited methods and the like

Active Publication Date: 2021-08-20
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the methods for synthesizing this type of compound are extremely limited. The existing molecular design and synthesis process of this type of compound have complex reaction steps and a long development cycle, which cannot meet the screening requirements of active lead compounds in the development of new drugs.

Method used

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  • Synthesis method and application of a kind of visible light-promoted dithiocarbamate compound
  • Synthesis method and application of a kind of visible light-promoted dithiocarbamate compound
  • Synthesis method and application of a kind of visible light-promoted dithiocarbamate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] At room temperature, add the corresponding iodobenzene (0.3mmol), carbon disulfide (0.8mmol), and the corresponding secondary amine (0.4mmol) to a 25ml Schlenk (Schlenk) tube filled with nitrogen and equipped with a magnetic stirring bar. Cesium carbonate (0.6mmol), 2.0mL DMSO was added with a syringe under nitrogen, the reaction tube was placed 3 cm away from a 23-watt fluorescent lamp, irradiated and stirred for 24 hours. After the reaction is over, add 2 mL of deionized water to the reaction liquid, mix well, and use 3 mL of ethyl acetate as the extractant each time to extract the crude product from the reaction liquid through liquid separation and extraction, combine the extracts, and rotate The evaporator was used to remove the solvent; the residue was purified with a silica gel column (the specification of silica gel was 200 mesh to 300 mesh, and the eluent was petroleum ether / ethyl acetate (20:1v / v)) to obtain 70.4 mg of the target product with a yield...

Embodiment 2

[0042]

[0043]At room temperature, add the corresponding iodobenzene (0.3mmol), carbon disulfide (1.2mmol), and the corresponding secondary amine (0.3mmol) to a 25ml Schlenk (Schlenk) tube filled with nitrogen and equipped with a magnetic stirring bar. Potassium carbonate (0.6mmol), 2.0mL DMSO was added with a syringe under nitrogen, and the reaction tube was placed 3 cm away from a 23-watt fluorescent lamp, and irradiated and stirred for 12 hours. After the reaction is over, add 2 mL of deionized water to the reaction solution, mix well, use 3 mL of ethyl acetate as the extractant each time to extract the crude product from the reaction solution, combine the extracts, and rotate The evaporator removed the solvent; the residue was purified with a silica gel column (the specification of silica gel was 200 mesh to 300 mesh, and the eluent was petroleum ether / ethyl acetate (15:1v / v)) to obtain 76.5 mg of the target product, with a yield of 81 %.

[0044] The obtained product...

Embodiment 3

[0049]

[0050] At room temperature, add the corresponding iodobenzene (0.3 mmol), carbon disulfide (0.9 mmol), and the corresponding secondary amine (0.75 mmol) to a 25 ml Schlenk (Schlenk) tube filled with nitrogen and equipped with a magnetic stirring bar, Sodium carbonate (0.9mmol), 2.0mL DMSO was added with a syringe under nitrogen, and the reaction tube was placed 3 cm away from a 23-watt fluorescent lamp, and irradiated and stirred for 22 hours. After the reaction is over, add 2 mL of deionized water to the reaction solution, mix well, use 3 mL of ethyl acetate as the extractant each time to extract the crude product from the reaction solution, combine the extracts, and rotate The evaporator was used to remove the solvent; the residue was purified with a silica gel column (the silica gel specification was 200 mesh to 300 mesh, and the eluent was petroleum ether / ethyl acetate (20:1v / v)) to obtain 58.6 mg of the target product with a yield of 70 %.

[0051] The obtain...

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Abstract

The invention relates to a method for synthesizing visible light-promoted dithiocarbamate compounds. The method uses substituted halogenated aromatic hydrocarbons, carbon disulfide and secondary amines as raw materials to construct dithiocarbamate compounds through a "one-pot method" under the irradiation of a 23-watt fluorescent lamp. The preparation method of the method is simple in process and device, can complete the reaction in one step, and has the advantages of few reaction steps, low cost, high yield, good functional group compatibility and the like.

Description

technical field [0001] The invention belongs to the field of photocatalytic organic synthesis, and in particular relates to a synthesis method and application of visible light-promoted dithiocarbamate compounds. Background technique [0002] Dithiocarbamate compounds have important application value in biomedicine, especially in the aspects of inhibiting tumor regeneration, antitumor, anti-Fusarium oxysporum and anti-Bacillus leprae. Key aspects are also an important source of raw materials. At present, its synthesis route is mainly through the reaction of hypervalent iodine and sodium dithioformate, Grignard reagent and disulfide, and phenylboronic acid or substituted benzene, carbon disulfide and amine compounds. In recent years, transition metal-catalyzed coupling reactions to construct dithiocarbamate compounds have also been developed a little. Although the previous method has made a significant contribution to the synthesis of this type of compound, there are still p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C333/24C07D295/21C07C333/20A61P31/04A61P35/00C07B60/00
CPCA61P31/04A61P35/00C07B61/02C07B2200/03C07C333/20C07C333/24C07D295/21
Inventor 杨道山颜秋莉
Owner QINGDAO UNIV OF SCI & TECH
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