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A kind of synthetic method of 6-cyanophenanthridine compounds

A technology of cyanophenanthridine and a synthesis method, applied in the field of organic compound synthesis, can solve problems such as harsh reaction conditions, and achieve the effects of mild reaction conditions, cheap and easy-to-obtain toxicity, and saving energy consumption

Active Publication Date: 2019-02-01
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 4. 6-(1H-1-tetrazolyl)phenanthridine synthesizes the target product at 600°C (see Journal of Organic Chemistry, 70(20), 7947-7955; 2005), the reaction conditions of this method are harsh

Method used

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  • A kind of synthetic method of 6-cyanophenanthridine compounds
  • A kind of synthetic method of 6-cyanophenanthridine compounds
  • A kind of synthetic method of 6-cyanophenanthridine compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] 0.5 mmol 1-azidovinyl-2-phenylbenzene (110.5 mg), 0.75 mmol tert-butyl nitrite (77.3 mg), 5 mL 1,2-dichloroethane were added to a 15 mL reaction tube. Next, magnetic stirring was performed at 100° C. for 5 hours. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure. The residue was packed into a column, and then separated by column chromatography. The mixed solvent of 1:1 is used as eluent, collects the eluent containing product, and the eluent is evaporated to remove solvent to obtain pure product 6-cyanophenanthridine. The material was a light yellow solid, 54% yield.

[0031] Characterization data: 1 H NMR (500MHz, CDCl 3 ):δ8.70–8.68(d,J=8.5Hz,1H),8.64–8.61(m,1H),8.47–8.46(d,J=8.0Hz,1H),8.29–8.26(m,1H), 8.01–7.98(m,1H),7.88–7.83(m,3H); 13 C NMR (125MHz, CDCl 3 ): δ143.7, 135.9, 132.8, 132.2, 131.1, 129.9, 129.7, 128.9, 126.8, 12...

Embodiment 2

[0033]

[0034] 0.5 mmol 1-azidovinyl-2-phenylbenzene (110.5 mg), 0.5 mmol tert-butyl nitrite (51.5 mg), 5 mL 1,2-dichloroethane were added to a 15 mL reaction tube. Next, magnetic stirring was performed at 100° C. for 5 hours. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure. The residue was packed into a column, and then separated by column chromatography. The mixed solvent of 1:1 is used as eluent, collects the eluent containing product, and the eluent is evaporated to remove solvent to obtain pure product 6-cyanophenanthridine. The material was a light yellow solid, 40% yield.

[0035] Characterization data: 1 H NMR (500MHz, CDCl 3 ):δ8.70–8.68(d,J=8.5Hz,1H),8.64–8.61(m,1H),8.47–8.46(d,J=8.0Hz,1H),8.29–8.26(m,1H), 8.01–7.98(m,1H),7.88–7.83(m,3H); 13 C NMR (125MHz, CDCl 3 ): δ143.7, 135.9, 132.8, 132.2, 131.1, 129.9, 129.7, 128.9, 126.8, 125...

Embodiment 3

[0037]

[0038]0.5 mmol 1-azidovinyl-2-phenylbenzene (110.5 mg), 0.75 mmol tert-butyl nitrite (77.3 mg), 5 mL acetonitrile were added to a 15 mL reaction tube. Next, magnetic stirring was performed at 100° C. for 5 hours. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure. The mixed solvent of 1:1 is used as eluent, collects the eluent containing product, and the eluent is evaporated to remove solvent to obtain pure product 6-cyanophenanthridine. The material was a light yellow solid, 48% yield.

[0039] Characterization data: 1 H NMR (500MHz, CDCl 3 ):δ8.70–8.68(d,J=8.5Hz,1H),8.64–8.61(m,1H),8.47–8.46(d,J=8.0Hz,1H),8.29–8.26(m,1H), 8.01–7.98(m,1H),7.88–7.83(m,3H); 13 C NMR (125MHz, CDCl 3 ): δ143.7, 135.9, 132.8, 132.2, 131.1, 129.9, 129.7, 128.9, 126.8, 125.5, 124.8, 122.4, 122.3, 115.8.

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Abstract

The invention discloses a synthetic method of 6-cyanophenanthridine compounds represented by formula II. The method comprises the following steps: stirring and reacting azide represented by formula I and tert-butyl nitrite in an organic solvent at 50-150 DEG C for 2-15 h, and separating and purifying the above obtained reaction solution to prepare the 6-cyanophenanthridine compounds represented by formula II. The method has the advantages of cheap, easily available and weakly toxic nitrogen source system, environmental protection, mild reaction conditions, good function group universality, and simplicity in operation.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing 6-cyanophenanthridine compounds. (2) Background technology [0002] Phenanthridine is an important class of heterocyclic compounds. Due to the potential biological activity and optoelectronic properties of these compounds, their structural units widely exist in some natural products, drugs and functional material molecules. For example, benzophenanthridine alkaloids are a class of natural nitrogen-containing compounds widely distributed in Papaveraceae and Rutaceae plants, which have significant antitumor and broad-spectrum antibacterial and other biological activities. As another example, Chelerythrine, Nitidine and Fagaronine all belong to phenanthridine alkaloids, the former has anti-cytotoxic and antibacterial activities, and the latter two have anti-cancer activities . Isometamidium (ISM) is composed of a group of complex isomers...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/12
CPCC07D221/12
Inventor 刘运奎任少波汪衡
Owner ZHEJIANG UNIV OF TECH