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Method for synthesizing 6-cyanophenanthridine compounds

A technology of cyanophenanthridine and compounds, which is applied in the field of synthesis of organic compounds, can solve problems such as complex catalytic systems and high reaction temperatures, and achieve the effects of simple reaction steps, mild reaction conditions, and good substrate adaptability

Inactive Publication Date: 2019-03-05
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method uses a complex catalytic system and requires a higher reaction temperature

Method used

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  • Method for synthesizing 6-cyanophenanthridine compounds
  • Method for synthesizing 6-cyanophenanthridine compounds
  • Method for synthesizing 6-cyanophenanthridine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] Add 0.3mmol 2-(4-tert-butyl)phenyl-α-azido-styrene, 0.6mmol sodium di-p-toluenesulfonamide, 0.6mmol potassium persulfate and 0.06mmol silver nitrate to a 15mL thick-wall pressure-resistant In the reaction tube, add 3 mL of toluene as solvent. Next, magnetic stirring was performed at 100° C. for 5 hours. After cooling to room temperature, two spoons of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and then the pure product was obtained by column chromatography (as petroleum ether / ethyl acetate = 50:1 as eluent). The material was an off-white solid in 55% yield.

[0034] Characterization data: 1 H NMR (500MHz, CDCl 3 ): δ8.63(d, J=8.0Hz, 1H), 8.53(d, J=8.5Hz, 1H), 8.42(d, J=8.0Hz, 1H), 8.24(d, J=1.5Hz, 1H ),7.98–7.89(m,2H),7.84–7.78(m,1H),1.49(s,9H); 13C NMR(125MHz,CDCl3)δ153.3,143.7,135.5,132.6,132.1,128.4,128.4,126.7, 126.6, 125.2, 122.4, 122.2, 1...

Embodiment 2

[0036]

[0037] Add 0.3mmol 2-(4-tert-butyl)phenyl-α-azido-styrene, 0.6mmol sodium di-p-toluenesulfonamide, 0.6mmol potassium persulfate and 0.06mmol silver nitrate to a 15mL thick-wall pressure-resistant In the reaction tube, 3 mL of tetrahydrofuran was added as a solvent. Next, magnetic stirring was performed at 100° C. for 3 hours. After cooling to room temperature, two spoons of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and then the pure product was obtained by column chromatography (as petroleum ether / ethyl acetate = 50:1 as eluent). The material was an off-white solid in 50% yield.

[0038] Characterization data: 1 H NMR (500MHz, CDCl 3 ): δ8.63(d, J=8.0Hz, 1H), 8.53(d, J=8.5Hz, 1H), 8.42(d, J=8.0Hz, 1H), 8.24(d, J=1.5Hz, 1H ),7.98–7.89(m,2H),7.84–7.78(m,1H),1.49(s,9H); 13C NMR(125MHz,CDCl3)δ153.3,143.7,135.5,132.6,132.1,128.4,128.4,126.7, 126.6, 125.2,...

Embodiment 3

[0040]

[0041] Add 0.3 mmol 2-(4-tert-butyl)phenyl-α-azido-styrene, 0.6 mmol sodium di-p-toluenesulfonamide, 0.6 mmol potassium persulfate and 0.06 mmol silver nitrite to 15 mL thick-walled Into the pressure reaction tube, add 3 mL of toluene as solvent. Next, magnetic stirring was performed at 100° C. for 6 hours. After cooling to room temperature, two spoons of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and then the pure product was obtained by column chromatography (as petroleum ether / ethyl acetate = 50:1 as eluent). The material was an off-white solid, 53% yield.

[0042] Characterization data: 1 H NMR (500MHz, CDCl 3 ): δ8.63(d, J=8.0Hz, 1H), 8.53(d, J=8.5Hz, 1H), 8.42(d, J=8.0Hz, 1H), 8.24(d, J=1.5Hz, 1H ),7.98–7.89(m,2H),7.84–7.78(m,1H),1.49(s,9H); 13C NMR(125MHz,CDCl3)δ153.3,143.7,135.5,132.6,132.1,128.4,128.4,126.7, 126.6, 125.2, 122.4, 122.2, 121.9,...

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Abstract

The present invention provides a method of synthesizing 6-cyanophenanthridine compounds. The synthesis method comprises the steps of: taking a substituted azide terminal olefin compound represented bya formula (I) as an initial substance, using sodium ditosylamide as a nitrogen source, conducting a reaction at 60-120 DEG C for 3-6 hours under the action of a silver catalyst, an oxidizing agent and a solvent, and conducting separation purification on the reaction solution to obtain the 6-cyanophenanthridine compound represented by the formula (II). The synthesis method of the invention has thecharacteristics of low environmental hazard, mild reaction conditions, simple operation and the like.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for preparing 6-cyanophenanthridine compounds. Background technique [0002] Phenanthridine is a very important class of nitrogen-containing hybrid compounds, which have potential biological activity and photoelectric properties, and are important structural units in some natural products, drugs and functional material molecules. For example, Fagaronine and Nitidine both belong to phenanthridine alkaloids, the former has anti-cancer activity, and the latter has anti-cytotoxic, antibacterial and other activities. Previously, phenanthridine was synthesized by condensation of 2-hydroxymethylcyclohexanone with aniline and aniline hydrochloride in ethanol solution, or reduction of 7,8,9,10-tetrahydrophenanthridinone. In recent years, due to the unique activity of phenanthridine compounds, various methods for synthesizing phenanthridine compounds have been newly ...

Claims

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Application Information

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IPC IPC(8): C07D221/12
Inventor 刘运奎郑立孟杨欢
Owner ZHEJIANG UNIV OF TECH
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