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Fluorine-containing phenanthridine derivative and preparation method thereof

A technology containing fluorophenanthridine and derivatives, which is applied in the field of fluorophenanthridine derivatives and their preparation, can solve the problems of difluoromethylene/cyclization and the like that have not yet been seen, and achieves high yield and substrate adaptability. Wide range of effects and easy operation

Active Publication Date: 2016-02-24
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no silver-catalyzed difluoromethylation / cyclization has been reported

Method used

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  • Fluorine-containing phenanthridine derivative and preparation method thereof
  • Fluorine-containing phenanthridine derivative and preparation method thereof
  • Fluorine-containing phenanthridine derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Preparation of 6-(difluoro(4-methoxyphenyl)methyl)phenanthridine adopts the following steps: in a 50 ml reaction flask, add

[0018] Add 0.102 g of silver nitrate, 1.37 g of ammonium persulfate, 0.15 g of potassium bicarbonate, 1.35 g of 2-isocyano-1,1'-biphenyl, 0.72 g of 2,2-difluoro-2-(4-methoxy Phenyl) potassium acetate, then add 25 ml of dimethyl sulfoxide, nitrogen protection, stir at 70 degrees for 8 hours, cool to room temperature after the reaction, remove the solvent, separate by silica gel column chromatography, the eluent is 10:1 A mixed solvent of petroleum ether and ethyl acetate was used to obtain 0.86 g of light yellow solid, with a yield of 86%.

[0019] 6-(difluoro(4-methoxyphenyl)methyl)phenanthridine, characterized in that the compound has the structure:

[0020]

[0021] Molecular formula: C 21 h 15 f 2 NO

[0022] Chinese name: 6-(difluoro(4-methoxyphenyl)methyl)phenanthridine

[0023] English name: 6-(difluoro(4-methoxyphenyl)methyl)phena...

Embodiment 2

[0032] Preparation of 6-(difluoro(4-methoxyphenyl)methyl)phenanthridine adopts the following steps: in a 500 ml reaction flask, add

[0033] Add 1.01 g of silver nitrate, 13.7 g of ammonium persulfate, 1.5 g of potassium bicarbonate, 13.5 g of 2-isocyano-1,1'-biphenyl, 7.2 g of 2,2-difluoro-2-(4-methoxy Phenyl) potassium acetate, then add 250 ml of dimethyl sulfoxide, nitrogen protection, stir at 80 degrees for 10 hours, cool to room temperature after the reaction, remove the solvent, and separate with silica gel column chromatography, the eluent is 10:1 The mixed solvent of sherwood oil and ethyl acetate obtained 8.844 grams of light yellow solid, yield 88%.

Embodiment 3

[0035] The following steps are used to prepare 6-(difluoro(4-methoxyphenyl)methyl)phenanthridine: in a 1-liter reaction flask, add

[0036] Add 10.1 grams of silver nitrate, 137 grams of ammonium persulfate, 15 grams of potassium bicarbonate, 135 grams of 2-isocyano-1,1'-biphenyl, 72 grams of 2,2-difluoro-2-(4-methoxy Phenyl) potassium acetate, then add 500 ml of dimethyl sulfoxide, nitrogen protection, stir at 80 degrees for 12 hours, cool to room temperature after the reaction, remove the solvent, separate by silica gel column chromatography, the eluent is 10:1 The mixed solvent of sherwood oil and ethyl acetate obtained 82.41 grams of light yellow solid, yield 82%.

[0037] According to the above-mentioned process route for preparing 6-(difluoro(4-methoxyphenyl)methyl)phenanthridine, the preparation method and structural characterization of other related compounds protected by this patent application are as follows:

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Abstract

The invention relates to a fluorine-containing phenanthridine derivative and a preparation method thereof. The structure of the derivative is as shown in the specification. In the structure, R1 is -H, -F or -Cl; R2 is -H or -CH3; and R3 is -H, -CH3 or -OMe. According to the invention, under the condition of silver catalysis, potassium difluoroacetate undergoes decarboxylation and then is coupled with o-phenylisonitrile, so synthesis of a fluorine-containing phenanthridine heterocyclic compound is completed.

Description

technical field [0001] The invention relates to a fluorine-containing phenanthridine derivative and a preparation method thereof. Background technique [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. A large number of studies have shown that after the introduction of fluorine atoms in heterocyclic compounds, its physical properties, chemical properties and physiological properties (such as lipophilicity, metabolic stability, binding ability to target proteins, cell membrane permeability and bioavailability) usually Significant improvement over its parent molecule. 5-Fluorouracil is a well-known anti-malignant drug, and it is the most powerful example that the physiological activity of the heterocyclic ring can be improved after introducing fluorine atoms. ...

Claims

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Application Information

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IPC IPC(8): C07D221/12
CPCC07D221/12
Inventor 李嘉亮万文麻国斌蒋海珍郝健
Owner SHANGHAI UNIV
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