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Sulfonamide compounds as well as preparation method and application thereof

A technology for sulfonamides and compounds, which is applied in the field of sulfonamides and their preparation, and can solve problems such as unfavorable applications and complex synthesis steps of sulfonamides

Active Publication Date: 2018-11-16
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides a sulfonamide compound and its preparation method and application, which solves the technical problem that the existing sulfonamide compound has complicated synthesis steps and is unfavorable for application in actual production

Method used

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  • Sulfonamide compounds as well as preparation method and application thereof
  • Sulfonamide compounds as well as preparation method and application thereof
  • Sulfonamide compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] Embodiment one 2-((triisopropylsilyl) acetylene) benzenesulfonamide (3a)

[0104]

[0105] Under nitrogen atmosphere, add arylsulfonamide compound 1a (14.4mg, 0.10mmol) and alkynylation reagent 2 (28μL, 0.20mmol) to a 15mL Schlenk reaction tube sequentially, when X=Br or I, no additional oxidant is needed; When X=H, AgOAc(2equiv.);), dichloro(pentamethylcyclopentadienyl)iridium dimer (2.3 mg, 0.0025 mmol) or dichloro(p-cymene) are required Ruthenium dimer (1.5mg, 0.0025mmol), silver bis(trifluoromethanesulfonyl)imide (4.2mg, 0.015mmol) or silver hexafluoroantimonate (5.2mg, 0.015mmol), cesium acetate (30mg, 0.36mmol), 1,2-dichloroethane (DCE, 1mL), react at 120°C for 12 hours. After the reaction was completed, it was cooled to room temperature, filtered through diatomaceous earth, and concentrated to obtain a crude product. The crude product was separated by chromatography on a prepared silica gel plate, and the selected developer or eluent was petroleum ether and ...

Embodiment 2

[0108] Example two 4-methyl-2-((triisopropylsilyl)acetylene)benzenesulfonamide (3b)

[0109]

[0110] Under nitrogen atmosphere, add arylsulfonamide compound 1b (17.1mg, 0.10mmol) and alkynylation reagent 2 (20μL, 0.15mmol) to a 15mL Schlenk reaction tube sequentially, when X=Br or I, no additional oxidant is needed; When X=H, AgOAc (2equiv.);), dichloro(pentamethylcyclopentadienyl) iridium dimer (2.3mg, 0.0025mmol) or dichloro(p-cymene) Ruthenium dimer (1.5mg, 0.0025mmol), silver bis(trifluoromethanesulfonyl)imide (4.2mg, 0.015mmol) or silver hexafluoroantimonate (5.2mg, 0.015mmol), cesium acetate (30mg, 0.36mmol), 1,2-dichloroethane (DCE, 1mL), react at 120°C for 12 hours. After the reaction was completed, it was cooled to room temperature, filtered through diatomaceous earth, and concentrated to obtain a crude product. The crude product was chromatographically separated on a prepared silica gel plate, and the selected developer or eluent was petroleum ether and ethyl a...

Embodiment 3

[0113] Example 3 4-((2Z,3E)1-methyl-3-phenyl-2-propenylhydrazone)-2-((triisopropylsilyl)acetylene)benzenesulfonamide (3c)

[0114]

[0115] Under nitrogen atmosphere, add sulfonamide compound 1c (31.5 mg, 0.10 mmol) and alkynylation reagent 2 (20 μ L, 0.15 mmol) sequentially to a 15 mL Schlenk reaction tube, when X=Br or I, no additional oxidant is needed; when X =H, need AgOAc (2equiv.);), dichloro(pentamethylcyclopentadienyl)iridium dimer (2.3mg, 0.0025mmol) or dichloro(p-methylcymenyl)ruthenium bis polymer (1.5mg, 0.0025mmol), silver bis(trifluoromethanesulfonyl)imide (4.2mg, 0.015mmol) or silver hexafluoroantimonate (5.2mg, 0.015mmol), cesium acetate (30mg, 0.36mmol ), 1,2-dichloroethane (DCE, 1 mL), reacted at 120°C for 18 hours. After the reaction was completed, it was cooled to room temperature, filtered through diatomaceous earth, and concentrated to obtain a crude product. The crude product was separated by chromatography on a prepared silica gel plate, and the s...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to sulfonamide compounds as well as a preparation method and an application thereof. The preparation method of the sulfonamide compounds comprises the following step: compounds shown as formula (I) are prepared from compounds shown as formula (II) and compounds shown as formula (III) under the action of a catalyst inpresence of an insert solvent, the compounds shown as the formula (I) are brand-new sulfonamide compounds and can be applied to the field of biomedicine. Substrates of the compounds are simple and easily available, for alkynylation reactions of direct carbon-hydrogen bonds of primary sulfonamides or secondary sulfonamides without additional orienting groups, few steps are exerted, operation is simple, the compounds have good atom economy and industrial application value, and the technical problems that the conventional sulfonamide compounds are synthesized through complicated steps and application to industrial production is difficult are solved.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a sulfonamide compound and its preparation method and application. Background technique [0002] Sulfonamide compounds are widely used in medicine, pesticides, dyes, etc. due to their important biological activities. In 1932, Bayer developed the first sulfonamide drug, prontosil, which won the Nobel Prize in Medicine in 1939. Prontosil is the first drug found to be effective against bacteria in infectious organisms so far, and it has played a milestone role in the development of sulfonamide drugs. A variety of sulfonamide drugs have been used clinically, so people's interest in sulfonamide research has also been stimulated. The pharmacological activities of sulfonamide derivatives mainly include: anti-tumor, anti-virus, anti-bacterial, anti-fungal, anti-tuberculosis and anti-parasitic [Wang Xiaoling, Wang Xianlong, Geng Rongxia, Zhou Chenghe, Chinese Journal of New Dr...

Claims

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Application Information

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IPC IPC(8): C07F7/08
CPCC07F7/0812C07F7/083
Inventor 李先纬吴国才霍延平
Owner GUANGDONG UNIV OF TECH
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