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Method for synthesizing 6-cyano phenanthridine compound

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

Active Publication Date: 2018-01-30
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-cyano phenanthridine compound
  • Method for synthesizing 6-cyano phenanthridine compound
  • Method for synthesizing 6-cyano phenanthridine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] Add 0.3 mmol of 2-(4-tert-butyl)phenyl-α-azido-styrene, 0.3 mmol of sodium azide, 0.6 mmol of iodobenzene diacetate, and 0.03 mmol of copper sulfate to a 15 mL thick-wall pressure-resistant reaction In the tube, add 3 mL of acetonitrile as solvent. Next, it was magnetically stirred at 40° C. for 4 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.

[0027] 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, ...

Embodiment 2

[0029]

[0030] Add 0.3 mmol of 2-(4-tert-butyl)phenyl-α-azido-styrene, 0.6 mmol of sodium azide, 0.6 mmol of iodobenzene diacetate, and 0.03 mmol of copper powder to a 15 mL thick-wall pressure-resistant reaction In the tube, 3 mL of tetrahydrofuran was added as a solvent. Next, stir magnetically at 40° C. for 4 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.

[0031] 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, ...

Embodiment 3

[0033]

[0034] Add 0.3 mmol of 2-(4-tert-butyl)phenyl-α-azido-styrene, 0.3 mmol of sodium azide, 0.6 mmol of iodobenzene diacetate, and 0.03 mmol of copper acetate to 15 mL of thick-wall pressure-resistant reaction In the tube, 3 mL of tetrahydrofuran was added as a solvent. Next, stir magnetically at 40° C. for 4 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.

[0035] 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, ...

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Abstract

The invention relates to a method for preparing 6-cyano phenanthridine and derivatives thereof. The method comprises the steps of adding an azido-terminal-substituted olefin compound represented by aformula I shown in the description, a nitrogen source, a catalyst, an oxidant and an organic solvent into a pressure-proof reactor, carrying out a full reaction at the temperature of 30 DEG C to 60 DEG C, and subjecting a reaction solution to separation and purification, thereby obtaining the 6-cyano phenanthridine represented by a formula II shown in the description and the derivatives thereof, wherein the nitrogen source comprises sodium azide, the catalyst comprises copper powder, cuprous bromide, copper sulfate, copper chloride, copper acetate or cuprous oxide, R1 and R2 in the formulae Iand II are separately the same, R1 is H, F or Cl, R2 is H, or H is monosubstituted or polysubstituted by methyl, chlorine, fluorine, phenyl, tert-butyl or methoxy. Compared with the prior art, the method has the advantages that the method is safe and environmentally friendly, no waste gas and waste water is produced, the substrate adaptability is good, all kinds of substituents can be aromatized / cyanated, the reaction conditions are mild, and the reaction steps are simple.

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 刘运奎徐峥鲍汉扬
Owner ZHEJIANG UNIV OF TECH
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