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

Method for synthesizing amino-substituted carbazole compound

A synthetic method and compound technology, applied in the direction of organic chemistry, can solve the problems of expensive catalysts, harsh reaction conditions, etc., and achieve the effect of simple operation, easy raw materials, and avoiding synthetic steps

Active Publication Date: 2017-05-10
HENAN NORMAL UNIV
View PDF1 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although most of the synthesis strategies in these literatures are relatively effective, there are still some problems to be solved, such as: the need to use expensive raw materials and catalysts, harsh reaction conditions, and the need for functional group protection and deprotection during the synthesis process.

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
  • Method for synthesizing amino-substituted carbazole compound
  • Method for synthesizing amino-substituted carbazole compound
  • Method for synthesizing amino-substituted carbazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013]

[0014] Add compound 1a (0.5mmol, 109.1mg), compound 2 (0.75mmol, 163.7mg), dicyclopentadienyl rhodium dichloride (0.025mmol, 15.5mg), copper acetate (0.05mmol, 9.1 mg) and acetonitrile (3 mL), the reaction tube was sealed in the presence of air, and then placed in an oil bath at 120° C. and stirred for 18 h. The reaction was quenched by adding 10 mL of water, extracted with ethyl acetate (10 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain the white solid product 5-ethoxyacyl-6-amino-11H-benzo[a]carbazole 3a (48.7mg, 32 %). The characterization data of this compound are as follows: 1 H NMR (600MHz, CDCl 3 )δ: 1.50(t, J=7.2Hz, 3H), 4.53(q, J=7.2Hz, 2H), 6.68(br s, 2H), 7.27-7.32(m, 2H), 7.39(t, J= 7.2Hz, 1H), 7.47(t, J=7.8Hz, 1H), 7.54(d, J=7.8Hz, 1H), 7.90(d, J=8.4Hz, 1H), 7.97(d...

Embodiment 2

[0016] According to the method described in Example 1, compound 1a (0.5mmol, 109.1mg), compound 2 (0.75mmol, 163.7mg), dicyclopentadienyl rhodium dichloride (0.025mmol, 15.5mg ), silver hexafluoroantimonate (0.1mmol, 34.3mg) and acetonitrile (3mL), the reaction tube was sealed in the presence of air, and then placed in an oil bath at 120°C and stirred for 18h. The reaction was quenched by adding 10 mL of water, extracted with ethyl acetate (10 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain the white solid product 5-ethoxyacyl-6-amino-11H-benzo[a]carbazole 3a (19.8mg, 13 %).

Embodiment 3

[0018] According to the method described in Example 1, compound 1a (0.5mmol, 109.1mg), compound 2 (0.75mmol, 163.7mg), dicyclopentadienyl rhodium dichloride (0.025mmol, 15.5mg ), copper acetate (0.05mmol, 9.1mg), silver hexafluoroantimonate (0.1mmol, 34.3mg) and acetonitrile (3mL), the reaction tube was sealed in the presence of air, and then placed in an oil bath at 120°C and stirred for 18h . The reaction was quenched by adding 10 mL of water, extracted with ethyl acetate (10 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. Filtrated, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain white solid product 5-ethoxyacyl-6-amino-11H-benzo[a]carbazole 3a (71.5mg, 47 %).

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 method for synthesizing an amino-substituted carbazole compound, belonging to the technical field of organic synthesis. According to key points of the technical scheme, the method disclosed by the invention comprises the following steps: dissolving 2-phenyl-3-cyanoindole compounds or 2-(thiazole-2-yl)-3-cyanoindole compounds and diazo compounds in a solvent; adding catalysts and additives, reacting at the temperature of 100-140 DEG C so as to obtain 6-aminobenzo[a]carbazole compounds or 5-aminothieno[a]carbazole compounds. The method disclosed by the invention starts from simple and easily prepared raw materials, the amino-substituted carbazole compounds are directly obtained by virtue of a one-pot cascade reaction, the synthetic process is easy and convenient to operate, the conditions are mild, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of amino-substituted carbazole compounds. Background technique [0002] Amino-substituted carbazole is an important nitrogen-containing heterocyclic skeleton, which is commonly found in functional organic molecules such as pesticides, medicines, and fluorescent reagents. In addition, amino-substituted carbazole compounds are also intermediates for the synthesis of various antiviral and antitumor lead compounds. In view of its importance, people have successively developed some methods of synthesizing these compounds. Although most of the synthetic strategies in these literatures are relatively effective, there are still some problems to be solved, such as: the need to use expensive raw materials and catalysts, harsh reaction conditions, and the need for functional group protection and deprotection during the synthesis process. Therefore,...

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): C07D209/80C07D495/04
CPCC07D209/80C07D495/04
Inventor 范学森张蓓蓓张新迎李彬郭胜海
Owner HENAN 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