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Synthesis method of phenanthridine and derivative of phenanthridine

A synthesis method and technology of derivatives, applied in the field of synthesis of phenanthridine and its derivatives, can solve the problems of not being universally applicable, difficult to obtain reaction raw materials, harsh reaction conditions, etc., and achieve strong substrate universality, economical Effects of energy consumption and mild reaction conditions

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

AI Technical Summary

Problems solved by technology

However, in these methods, there are still certain limitations: such as the raw materials are not easy to obtain, the reaction conditions are harsh, there are many steps, the yield is not high, and it does not have universal applicability, etc.

Method used

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  • Synthesis method of phenanthridine and derivative of phenanthridine
  • Synthesis method of phenanthridine and derivative of phenanthridine
  • Synthesis method of phenanthridine and derivative of phenanthridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] Add 96.3mg (0.3mmol) of 2-phenylbenzenesulfonimide, 106.3mg (0.3mmol) of Selectfluor and 1.0mg (0.015mmol) of Cu powder into a 25mL thick-walled pressure-resistant tube, and add 3mL of acetonitrile under nitrogen protection as a solvent. Next, it was magnetically stirred at 50° 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, each time take the organic layer containing dichloromethane and target product, i.e. the extract, and at the end Add 192.6 mg column chromatography silica gel (100-200 mesh) to the extract once, and remove the solvent by distillation under reduced pressure, and separate the residue by column chromatography, and use a mixture of petroleum ether and ethyl acetate with a volume ratio of 10:1 Eluted as an eluent, collected the eluate containing the target product, and distilled off the solvent to obtain a pure produc...

Embodiment 2

[0028]

[0029] Add 100.5mg (0.3mmol) of 2-(4'-methylphenyl)phenylbenzenesulfonimide, 136.2mg (0.6mmol) of DDQ and 1.0mg (0.015mmol) of Cu powder into a 25mL thick-walled pressure-resistant tube 0.9 mL of 1,2-dichloroethane was added as a solvent under the protection of nitrogen. Next, it was magnetically stirred at 50° C. for 12 hours. Then, transfer the reaction solution to a 25mL separatory funnel and add 3mL ethyl acetate and 8mL water to extract simultaneously, extract 3 times, and get the organic layer containing ethyl acetate and the target product every time, i.e. the extract, and at the end Add 502.5 mg column chromatography silica gel (100-200 mesh) to the extract once, and remove the solvent by distillation under reduced pressure, and separate the residue by column chromatography, and use a mixture of petroleum ether and ethyl acetate with a volume ratio of 10:1 Eluted as an eluent, collected the eluate containing the target product, and distilled off the solven...

Embodiment 3

[0032]

[0033]Add 108.9mg (0.3mmol) of 2-(4'-isopropylphenyl)phenylbenzenesulfonimide, 368.9mg (0.6mmol) of Oxone and 1.9mg (0.03mmol) of Cu powder into a 25mL thick-wall pressure-resistant In a separate tube, add 3 mL of 1,4-dioxane as a solvent under nitrogen protection. Next, it was magnetically stirred at 50° C. for 24 hours. Then, transfer the reaction solution to a 25mL separatory funnel and add 12mL of dichloromethane and 8mL of water to extract at the same time, extract 3 times, each time get the organic layer containing dichloromethane and target product, i.e. the extract, and in the last Add 326.7 mg of column chromatography silica gel (100-200 mesh) to the extract, and remove the solvent by distillation under reduced pressure, and separate the residue by column chromatography, using a mixture of petroleum ether and ethyl acetate with a volume ratio of 10:1 as The eluent was eluted, the eluate containing the target product was collected, and the solvent was evap...

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Abstract

The invention discloses a synthesis method of phenanthridine as shown in a formula (I) and a derivative of the phenanthridine. In the synthesis method, o-arylphenylsulfimide shown as a formula (II) isused as a raw material and reacts in an organic solvent under the action of a [Cu] / Selectfluor catalyst to obtain a corresponding target product (I). The synthesis method disclosed by the invention has the advantages of cheap and easily available and low-toxicity catalyst, environmental friendliness, mild reaction conditions, high universality of functional group and easiness and convenience in operation. The formulas (I) and (II) are shown in the description.

Description

(1) Technical field [0001] The invention relates to a synthesis method of organic compounds, in particular to a synthesis method of phenanthridine and derivatives thereof. (2) Background technology [0002] As a representative heterocyclic unit widely present in some natural products, alkaloids and functional material molecules, phenanthridine exhibits a wide range of biological activities, such as antimalarial, antitumor, anticytotoxic, antibacterial, etc. . Therefore, exploring efficient and selective synthesis methods of phenanthridine and its derivatives is of great significance in the fields of medicinal chemistry and materials science. [0003] Among the reported synthetic methods of phenanthridine and its derivatives, intramolecular cyclization of ortho-substituted diaryl compounds is the main synthetic method. At present, the synthetic methods of relevant phenanthridine and its derivatives reported at home and abroad mainly contain the following methods: benzyne me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
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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