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Preparation method of 6-phenyl phenanthridine compound

A technology for phenylphenanthridine and compounds, which is applied in the field of preparation of organic compounds, can solve the problems of expensive visible light or thermal energy catalysts, expensive catalysts, harsh reaction conditions, etc., and achieves low-cost and easy-to-obtain catalysts and universal substrates. The effect of strong performance and easy availability of raw materials

Inactive Publication Date: 2018-03-09
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, the preparation method of relevant 6-phenylphenanthridine of domestic and foreign reports mainly contains following several methods: (1) utilize Pictet-Hubert chemical reaction synthesis method (referring to Ber.Dtsch.Chem.Ges.1896,29,1182; J.Chem.Soc.1931,2447-2456.), this method needs higher reaction temperature (more than 200 degrees) and needs to use the organophosphorus compound that has toxicity, and reaction condition is very harsh; (2) by N-( 2-halophenyl)imine cyclization / aromatization synthesis (see J.Org.Chem.2011,76,9507-9513), the catalyst used in this method is expensive and uses toxic organophosphorus ligands; (3) Using ortho-aryloxime or o-aryloxime ether compounds as raw materials, it can be synthesized by visible light or heating to catalyze the C-H bond functionalization (see Angew.Chem.Int.Ed.2015, 54, 4055-4059; J .Org.Chem.2015,80,256-265), this method requires high visible light or heat energy and the catalyst used is expensive

Method used

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  • Preparation method of 6-phenyl phenanthridine compound
  • Preparation method of 6-phenyl phenanthridine compound
  • Preparation method of 6-phenyl phenanthridine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] Add 119.7mg (0.3mmol) N-[1-phenyl-1'-biphenyl]benzenesulfonamide, 212.6mg (0.6mmol) Selectfluor and 5.7mg (0.03mmol) CuI into a 25mL thick-walled pressure-resistant tube, Acetonitrile was used as solvent, and the dosage was 3 mL. Next, it was magnetically stirred at 70° C. for 12 hours. Then, transfer the reaction solution to a 25mL separatory funnel and add 8mL of dichloromethane and 8mL of water to extract simultaneously, extract 3 times, get the organic layer containing dichloromethane and target product each time, i.e. the extract, and in the last Add 239.4 mg of column chromatography silica gel (100-200 mesh) to the extract, remove the solvent by distillation under reduced pressure (vacuum degree is 0.08kPa), and separate the residue by column chromatography. The volume ratio of petroleum ether and ethyl acetate is 10 : 1 mixed solution was eluted as eluent, the eluate containing target product was collected, and the solvent was evaporated to obtain a ...

Embodiment 2

[0028]

[0029] 136.5 mg (0.3 mmol) N-[1-phenyl-1'-biphenyl (4'-tert-butyl)] benzenesulfonamide, 204.3 mg (0.9 mmol) DDQ and 6.5 mg (0.045 mmol) CuBr were added to In a 25mL thick-walled pressure-resistant tube, acetone is used as a solvent, and the dosage is 3mL. Next, it was magnetically stirred at 100° C. for 24 hours. Then, transfer the reaction solution to a 25mL separatory funnel and add 12mL ethyl acetate and 8mL water to extract at the same time, extract 3 times, get the organic layer containing ethyl acetate and the target product each time, i.e. the extract, and in the last Add 273 mg of column chromatography silica gel (100-200 mesh) to the extract, remove the solvent by distillation under reduced pressure (vacuum degree is 0.08kPa), and separate the residue by column chromatography. The volume ratio of petroleum ether and ethyl acetate is 10: The mixed solution of 1 was eluted as an eluent, and the eluate containing the target product was collected, and the sol...

Embodiment 3

[0032]

[0033] Add 129.9 mg (0.3 mmol) N-[1-phenyl-1'-biphenyl(4'-chloro)]benzenesulfonamide, 553.3 mg (0.9 mmol) Oxone and 8.6 mg (0.045 mmol) CuI to a 25 mL thick In the wall pressure tube, toluene is used as solvent, and the dosage is 0.9mL. Next, magnetic stirring was performed at 120° C. for 36 hours. Then, transfer the reaction solution to a 25mL separatory funnel and add 3mL dichloromethane and 8mL water to extract simultaneously, extract 3 times, get the organic layer containing dichloromethane and target product at each time, i.e. the extract, and in the last Add 259.8 mg of column chromatography silica gel (100-200 mesh) to the extract, remove the solvent by distillation under reduced pressure (vacuum degree is 0.08kPa), and separate the residue by column chromatography. The volume ratio of petroleum ether to ethyl acetate is 10 : The mixed solution of 1 was eluted as the eluent, and the eluate containing the target product was collected, and the solvent was eva...

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Abstract

The invention discloses a preparation method of 6-phenyl phenanthridine compound which is shown in a formula (I). According to the preparation method, N-(1-phenyl-1'-biphenyl)benzene sulfonamide shownin a formula (II) is utilized as a raw material, and the N-(1-phenyl-1'-biphenyl)benzene sulfonamide reacts in CH3CN under the action of a [Cu] / Selectfluor catalysome agent to prepare a correspondingtarget product formula (I). The synthesizing method disclosed by the invention has the advantages of low catalyst cost, small toxicity, environmental friendliness, moderate reaction condition, good functional group popularization, convenience in operation and the like. The formula (I) and the formula (II) are shown in the description.

Description

(1) Technical field [0001] The invention relates to a preparation method of organic compounds, in particular to a preparation method of 6-phenylphenanthridine compounds. (2) Background technology [0002] Phenanthridine is an important class of compounds widely used in N-heteroaryl materials and medicinal chemistry. Among them, substituted phenanthridines have potential therapeutic utility in multifunctional scaffolds and building block drugs. For example, drugs with this framework have a wide range of biological activities: antibacterial, anti-tuberculosis, anti-tumor activities, etc. Therefore, the research and development of the related preparation technology of 6-phenylphenanthridine in substituted phenanthridine has broad application prospects. [0003] At present, the preparation method of relevant 6-phenylphenanthridine of domestic and foreign reports mainly contains following several methods: (1) utilize Pictet-Hubert chemical reaction synthesis method (referring to...

Claims

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Application Information

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IPC IPC(8): C07D221/12
CPCC07D221/12
Inventor 刘运奎施冬冬徐峥
Owner ZHEJIANG UNIV OF TECH
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