Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

5,6-dihydrophenanthine compound and preparation method thereof

A technique for dihydrophenanthidine and compounds, applied in the field of 5,6-dihydrophenanthidine compounds and their preparation, achieving the effects of wide substrate range, high yield, and simple and easy-to-obtain catalysts

Inactive Publication Date: 2016-06-22
LUOYANG NORMAL UNIV
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with the classical coupling reaction, the coupling reaction activated by the carbon-hydrogen bond saves the process of preparing metal reagents, has higher atom economy and synthesis efficiency, and is the most ideal synthesis method. Synthesis of 5,6-dihydrophenanthidines from amines via hydrogen transfer reaction and carbon-hydrogen bond activation has not been reported yet

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
  • 5,6-dihydrophenanthine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: the preparation of 5,6-dihydrophenanthidine

[0018] Under the protection of inert gas (such as high-purity nitrogen), add 1.0mmol o-bromobenzyl alcohol, 1.2mmol aniline, 0.005mmol [Ir(cod )Cl] 2 , 0.02mmol palladium trifluoroacetate, 1.0mmol silver carbonate, 0.05mmol tricyclohexylphosphine, 1.0mmol cesium hydroxide and 5ml dioxane, replace the reaction tube with nitrogen for 3 times, and then heat to 110°C, the reaction was refluxed for 12 hours. The oil bath was removed, and the water bath was lowered to room temperature; 3ml of water was added to the reaction solution, extracted three times with 5ml of dichloromethane, the organic phases were combined and washed with anhydrous MgSO 4 Dry for 30 minutes and filter; the filtrate is concentrated with a rotary evaporator, and the concentrated solid is recrystallized with dichloromethane as a solvent to obtain a pure product with a yield of 80%. The nuclear magnetic analysis data of this product are as f...

Embodiment 2

[0020] Embodiment 2: the preparation of 7-methyl-5,6-dihydrophenanthidine

[0021] Under the protection of an inert gas (such as high-purity nitrogen), add 1.0mmol o-methylbenzyl alcohol, 1.5mmol o-bromoaniline, 0.01mmol [ Ir(cod)Cl] 2 , 0.05mmol palladium acetate, 2.0mmol silver carbonate, 0.08mmol tricyclohexylphosphine, 2.0mmol potassium hydroxide and 5ml toluene, replace the reaction tube with nitrogen for 3 times, then heat to 110°C with an oil bath under magnetic stirring, and react to reflux 20 hours. The oil bath was removed, and the water bath was lowered to room temperature; 3ml of water was added to the reaction solution, extracted three times with 5ml of dichloromethane, the organic phases were combined and washed with anhydrous MgSO 4 Dry for 30 minutes and filter; the filtrate is concentrated with a rotary evaporator, and the concentrated solid is recrystallized with dichloromethane as a solvent to obtain a pure product with a yield of 88%. The nuclear magneti...

Embodiment 3

[0023] Example 3: Preparation of 9-methyl-5,6-dihydrophenanthidine

[0024] Under the protection of inert gas (such as high-purity nitrogen), add 1.0mmol p-methylbenzyl alcohol, 2.0mmol o-bromoaniline, 0.015mmol [ Ir(cod)Cl] 2 , 0.1mmol palladium chloride, 1.5mmol silver trifluoroacetate, 0.2mmol tricyclohexylphosphine, 1.5mmol cesium carbonate and 5ml benzene, replace the reaction tube with nitrogen for 3 times, then heat to 80°C with an oil bath under magnetic stirring, The reaction was refluxed for 24 hours. The oil bath was removed, and the water bath was lowered to room temperature; 3ml of water was added to the reaction solution, extracted three times with 5ml of dichloromethane, the organic phases were combined and washed with anhydrous MgSO 4 Dry for 30 minutes and filter; the filtrate is concentrated with a rotary evaporator, and the concentrated solid is recrystallized with dichloromethane as a solvent to obtain a pure product with a yield of 83%. The nuclear magn...

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 relates to a 5,6-dihydrophenanthridine compound and a preparation method thereof. The formula of the compound is shown in the specification. The preparation method of the compound comprises the following steps of adding o-bromoarylamine and aryl methanol (or o-bromo aryl methanol and aryl amine), [Ir (cod) Cl] 2 (cod is equal to 1,5-cyclooctadiene), a palladium salt, a silver salt, tricyclohexyl phosphine and the base into a organic solvent, heating for reflux under the protection of N2, after the reaction is completed, filtering, evaporating to dryness, and recrystallizing to obtain the 5,6-dihydrophenanthridine compound. The 5,6-dihydrophenanthridine compound is synthesized in one step by using the method and the method has the advantages of mild reaction conditions, high yield, cost-effective reaction and wide application prospects.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to 5,6-dihydrophenanthidine compounds and a preparation method thereof. Background technique [0002] Pyridine derivatives are an important class of isoquinoline alkaloids, which have good biological and pharmacological activities and are widely used in the pharmaceutical industry. Pyridine derivatives were first extracted from Papaveraceae and Rutaceae plants, and their product types and yields are limited. Some important phenanthidine derivatives cannot meet market demand through this method. In the past ten years, the synthesis method of phenanthidine derivatives has been greatly developed, but the reaction steps are many, the conditions are harsh, the operation is cumbersome, the general yield is low, and the 5,6-dihydrophenanthidine compounds are still rare There are few reports. At present, metal-catalyzed synthesis of phenanthridine derivatives is the most studied...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/12
CPCC07D221/12
Inventor 王志强许春莺付维军李红梅徐晨
Owner LUOYANG NORMAL UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com