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Method for catalytically preparing 6(5H)-phenanthridine ketone by copper component

A copper compound, a catalytic preparation technology, applied in the direction of organic chemistry, etc., to achieve the effect of facilitating the development of industrial production, broad application prospects, and simple recycling

Inactive Publication Date: 2013-03-20
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are no public documents and patents at home and abroad that use copper compounds to catalyze N-arylation to form phenanthrene

Method used

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  • Method for catalytically preparing 6(5H)-phenanthridine ketone by copper component
  • Method for catalytically preparing 6(5H)-phenanthridine ketone by copper component
  • Method for catalytically preparing 6(5H)-phenanthridine ketone by copper component

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the synthesis of 6 (5H)-phenanthridone

[0027] Substrate 197mg (1mmol) 2-phenylbenzamide, catalyst 19mg (0.1mmol) CuI, ligand 52mg (0.2mmol) PPh 3 , base 224mg (2mmol) KO-tBu, and solvent 3ml o-xylene were added to a 30ml sealed tube in an air environment. Then the sealed tube was placed in an oil bath at 120°C for 12 h. After the reaction, the reaction liquid was cooled to room temperature, 80 ml of saturated brine was added, and then extracted three times with 100 ml of ethyl acetate, and the organic layers were combined. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 2 as eluent) to obtain 175.5 mg of white solid with a yield of 90%.

[0028] 1 H NMR (400MHz, DMSO-d 6 ):δ11.69(s,1H),8.52(d,J=8.0Hz,1H),8.40(d,J=8.0Hz,1H),8.83(d,J=8.0Hz,1H),7.86(t ,J=7.6Hz,1H),7.65(t,J=7.6Hz,1H),7.50(t,J=7.6H...

Embodiment 2

[0031] Embodiment 2: the synthesis of 3,8-dimethyl-6 (5H)-phenanthridinone

[0032] Substrate 225mg (1mmol) 4,4′-dimethyl-[1,1′-biphenyl]-2-amide, catalyst 19mg (0.1mmol) CuI, ligand 52mg (0.2mmol) PPh 3 , base 224mg (2mmol) KO-tBu, and solvent 3ml o-xylene were added to a 30ml sealed tube in an air environment. Then the sealed tube was placed in an oil bath at 120°C for 12 h. After the reaction, the reaction liquid was cooled to room temperature, 80 ml of saturated brine was added, and then extracted three times with 100 ml of ethyl acetate, and the organic layers were combined. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 2 as eluent) to obtain 174.0 mg of white solid with a yield of 78%.

[0033] 1 H NMR (400MHz, DMSO-d 6 ):δ11.54(s,1H),8.33(d,J=8.0Hz,1H),8.21(d,J=8.0Hz,1H),8.10(s,1H),7.64(d,J=8.0Hz ,1H),7.14(...

Embodiment 3

[0036] Embodiment 3: the synthesis of 8-methoxy-3-methyl-6 (5H)-phenanthridinone

[0037] Substrate 241mg (1mmol) 4-methoxy-4′-methyl-[1,1′-biphenyl]-2-amide, catalyst 19mg (0.1mmol) CuI, ligand 52mg (0.2mmol) PPh 3 , base 224mg (2mmol) KO-tBu, and solvent 3ml o-xylene were added to a 30ml sealed tube in an air environment. Then the sealed tube was placed in an oil bath at 120°C for 12 h. After the reaction, the reaction liquid was cooled to room temperature, 80 ml of saturated brine was added, and then extracted three times with 100 ml of ethyl acetate, and the organic layers were combined. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 2 as eluent) to obtain 203.2 mg of white solid with a yield of 85%.

[0038] 1 H NMR (400MHz, DMSO-d 6 ):δ11.65(s,1H),8.39(d,J=8.0Hz,1H),8.18(d,J=8.0Hz,1H),7.73(s,1H),7.42(d,J=8.8Hz...

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Abstract

The invention relates to a method for catalytically preparing 6(5H)-phenanthridine ketone by a copper component. The method comprises the step of catalyzing a 2-phenyl benzamide derivative to carry out N-arylated reaction to generate a 6(5H)-phenanthridine ketone derivative by the copper component under the coordination of a ligand in an air environment or airtight environment. The method can be carried out in the air environment, and the catalyst used is simple and easy to obtain and high in reaction yield. The method provided by the invention is beneficial for industrial production.

Description

technical field [0001] The invention relates to a method for preparing 6(5H)-phenanthridinone by catalyzing a copper compound, belonging to the fields of organic synthesis and metal catalysis. Background technique [0002] 6(5H)-phenanthridinones are a class of alkaloid compounds containing nitrogen atoms. Such alkaloids have potent anti-tumor, anti-virus, inhibitory acetylcholinesterase and other biological activities. Some of these alkaloids have been used to treat myasthenia gravis, myopathy, and neurological disorders. Therefore, the development of synthetic methods for phenanthridinones has important practical value. At present, there are some methods for the synthesis of phenanthridinone compounds. For example, phenanthridone can be synthesized by Suzuki Cross-Coupling to substituted 2'-fluorobiphenyl-2-carbonitrile, and then potassium hydroxide is added to promote anion ring closure to form phenanthrene. In addition, 9-fluorenone oxime undergoes Beckmann rearrange...

Claims

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Application Information

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IPC IPC(8): C07D221/12
Inventor 谭泽桂清文刘吉旦戴枫林郭汝庆
Owner HUNAN UNIV
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