Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Visible light promoted synthesis method and application of dithiocarbamate compounds

A technology of dithiocarbamic acid and ester compounds, which is applied in the field of photocatalytic organic synthesis, can solve problems such as limited methods, long research and development cycle, and complex reaction steps, and achieve simple processes and devices, fewer reaction steps, and low cost Effect

Active Publication Date: 2020-01-10
QINGDAO UNIV OF SCI & TECH
View PDF1 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Visible light promoted synthesis method and application of dithiocarbamate compounds
  • Visible light promoted synthesis method and application of dithiocarbamate compounds
  • Visible light promoted synthesis method and application of dithiocarbamate compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] At room temperature, add the corresponding iodobenzene (0.3 mmol), carbon disulfide (0.8 mmol), and the corresponding secondary amine (0.4 mmol) to a 25 ml 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, and the reaction tube was placed 3 cm away from a 23-watt fluorescent lamp, and irradiated and stirred for 24 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 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 of 78 %.

[0037] The obta...

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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a visible light-promoted synthesis method of dithiocarbamate compounds. The method uses substituted halogenated aromatic hydrocarbon, carbon disulfide and secondary amine as raw materials to construct the dithiocarbamate compounds through a one-pot method under the irradiation of a 23-watt fluorescent lamp. The preparation method has simple process and device, can completethe reaction in one step, and has the advantages of fewer 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C333/24C07D295/21C07C333/20A61P31/04A61P35/00C07B60/00
CPCC07C333/24C07D295/21C07C333/20A61P31/04A61P35/00C07B61/02C07B2200/03
Inventor 杨道山颜秋莉
Owner QINGDAO UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com