Synthesis method of 6-substituted phenanthridine compound

A synthesis method and compound technology, applied in the field of organic compound synthesis, can solve the problems of high reaction temperature control requirements, limited compound synthesis, and high reaction temperature requirements, and achieve the effects of simple raw materials, simple operation, and easy availability of raw materials

Inactive Publication Date: 2018-03-13
ZHEJIANG UNIV OF TECH
View PDF3 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the synthetic method of relevant 6-substituted phenanthridines reported at home and abroad mainly contains the following several methods: (1) adopt Bischler-Napieralski cyclization method (referring to J.Chem.Soc.1950,703-711 and J.Chem. Soc.1957,505-509), this method needs to add P 4 o 10 , POCl 3 or PCl 5 , Harsh conditions limit the synthesis of a variety of resistant functional groups, so that the synthesis of some compounds is limited; (2) Synthesis by cyclization of o-aryl benzohydroxime under microwave conditions (see J.Org.Chem.2008,73, 5558), the mechanism of this method is a free radical reaction, and its reaction temperature requirement is relatively high (above 100 degrees); (3) use fluorinated aromatic hydrocarbons and nitriles as raw materials, synthesized through 1,2-aryne intermediates (see Org.Lett .200

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis method of 6-substituted phenanthridine compound
  • Synthesis method of 6-substituted phenanthridine compound
  • Synthesis method of 6-substituted phenanthridine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]

[0024] Add 119.7mg (0.3mmol) of N-[1-phenyl-1'-biphenyl]benzenesulfonamide, 212.6mg (0.6mmol) of Selectfluor and 1.7mg (0.03mmol) of Fe powder into a 25mL thick-walled pressure-resistant tube , acetonitrile as solvent, the dosage is 3mL. Next, it was magnetically stirred at 80° 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

[0027]

[0028] 136.5mg (0.3mmol) N-[1-phenyl-1'-biphenyl (4'-tert-butyl)] benzenesulfonamide, 204.3mg (0.9mmol) DDQ and 5.7mg (0.045mmol) FeCl 2Add it to a 25mL thick-walled pressure-resistant tube, using 1,2-dichloroethane as a solvent, and the dosage is 1.5mL. Next, it was magnetically stirred at 90° C. for 24 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, 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 solvent ...

Embodiment 3

[0031]

[0032] 129.9mg (0.3mmol) of N-[1-phenyl-1'-biphenyl(4'-chloro)]benzenesulfonamide, 645.5mg (1.05mmol) of Oxone and 26.6mg (0.09mmol) of FeBr 3 Add it to a 25mL thick-walled pressure-resistant tube, using 1,4-dioxane as a solvent, and the dosage is 3mL. Next, magnetic stirring was performed at 130° C. for 36 hours. Then, transfer the reaction solution to a 25mL separatory funnel and add 15mL 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 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, a...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a synthesis method of a 6-substituted phenanthridine compound represented by a formula (I), wherein a N-[1-phenyl-1'-biphenyl]benzenesulfonamide compound represented by a formula (II) is used as a raw materials and is subjected to a reaction in an organic solvent under the action of a [Fe]/Selectfluor catalyst to prepare a corresponding target product represented by the formula (I). According to the present invention, the synthesis method has advantages of environmental friendliness, mild reaction conditions, good functional group popularity, easy operation and the like, and uses the catalyst with advantages of low cost, easy availability and low toxicity. The formulas (I) and (II) are defined in the specification.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing 6-substituted phenanthridine compounds. (2) Background technology [0002] Phenanthridine widely exists in a series of diverse compound structures, including a wide range of important natural products, compounds with antiviral, antiprotozoal and antitumor biological and drug therapeutic activities and functional material compounds. The molecule contains this Fragments have received considerable attention in medicine and materials, so that chemists have focused most of their efforts on the synthesis of phenanthridine derivatives. Therefore, research and development of related synthesis technologies of phenanthridine derivatives 6-substituted phenanthridines have broad application prospects. [0003] At present, the synthetic method of relevant 6-substituted phenanthridines reported at home and abroad mainly contains the following several...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D221/12
CPCC07D221/12
Inventor 刘运奎施冬冬徐峥
Owner ZHEJIANG UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap