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

5,12-dihydro-5-phenyl indole (3,2-a)carbazole synthesizing method

A technology of phenylindole and phenylcarbazole, applied in the field of organic chemical synthesis, can solve the problems of difficult removal of isomers, unsuitable operation, high cost, and achieve the effects of easy separation, avoidance of waste and fewer by-products

Active Publication Date: 2018-04-03
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
View PDF5 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

WO2013032284 reports a method for the synthesis of 5,12-dihydro-5-phenylindolo[3,2-a]carbazole using 3-boronic acid-N-phenylcarbazole as a starting material. The rate is low, the generated isomer is difficult to remove, it is not suitable for operation, and the cost is high, so it is necessary to explore a new method suitable for industrial production

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
  • 5,12-dihydro-5-phenyl indole (3,2-a)carbazole synthesizing method
  • 5,12-dihydro-5-phenyl indole (3,2-a)carbazole synthesizing method

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0022] Dissolve 51.7 g (0.2 mol) of 4-amino-N-phenylcarbazole in 200 mL of acetonitrile in a 1 L three-necked flask, add 36.4 g (0.18 mol) of 40% hydrobromic acid aqueous solution by mass, and control the reaction temperature- Slowly add 18.4 mL (0.18 mol) of 30% hydrogen peroxide dropwise at 20 °C. After the dropwise addition is complete, the temperature is naturally raised to react overnight. The reaction solution is washed with aqueous sodium bisulfite solution, the organic layer is separated, and hydrochloric acid is added to obtain 3-bromo-4-amino -N-phenylcarbazole hydrochloride, 61.9 g after drying; under the protection of argon, 61.9 g (0.16 mol) 3-bromo-4-amino-N-phenylcarbazole hydrochloride, 33.1 g ortho Bromophenylboronic acid, 20.2 g of cesium carbonate, and 200 mL of N-methylpyrrolidone solvent were added to a 1 L three-necked flask to replace the air system, and then 0.04 g of palladium acetate and 0.16 g of (R,R)-1,2 -bis[(2-methoxyphenyl)phenylphosphino]ethane...

example 2

[0025] In a 2 L three-necked flask, 129.2 g (0.5 mol) of 4-amino-N-phenylcarbazole was dissolved in 1000 mL of acetonitrile, 95.1 g (0.47 mol) of 40% hydrobromic acid aqueous solution was added, and the reaction temperature was controlled at 0 Slowly add 48.0 mL (0.47 mol) of 30% hydrogen peroxide dropwise at ℃. After the dropwise addition is complete, let the temperature rise naturally and react overnight. N-phenylcarbazole hydrochloride, 160.6 g after drying; under argon protection, 160.6 g (0.42 mol) 3-bromo-4-amino-N-phenylcarbazole hydrochloride, 84.3 g o-bromo Add phenylboronic acid, 55.2g cesium carbonate, and 800 mL N-methylpyrrolidone solvent into a 2 L three-neck flask to replace the air system, then add 0.5 g palladium acetate and 1.9 g (R,R)-1,2-bis [(2-Methoxyphenyl) phenylphosphino]ethane, reflux reaction, detection by liquid chromatography, after the end, add 800 mL of ice water to terminate the reaction, extract with 800 mL of dichloromethane, organic layer sod...

example 3

[0027] In a 5 L three-necked flask, 206.7 g (0.8 mol) of 4-amino-N-phenylcarbazole was dissolved in 1600 mL of acetonitrile, and 137.5 g (0.68 mol) of 40% hydrobromic acid aqueous solution was added to control the reaction temperature- Slowly add 89.8mL (0.88mol) of 30% hydrogen peroxide dropwise at 20°C. After the dropwise addition is complete, the temperature is naturally raised to react overnight. The reaction solution is washed with aqueous sodium bisulfite solution, the organic layer is separated, and hydrochloric acid is added to obtain 3-bromo-4-amino -N-phenylcarbazole hydrochloride, 248.1 g after drying; under the protection of argon, 248.1 g (0.66 mol) 3-bromo-4-amino-N-phenylcarbazole hydrochloride, 132.3 g ortho Add bromophenylboronic acid, 71.5 g cesium carbonate, and 1500 mL N-methylpyrrolidone solvent into a 5 L three-necked flask to replace the air system, then add 1.5 g palladium acetate and 6.0 g (R,R)-1,2- Bis[(2-methoxyphenyl)phenylphosphino]ethane, reflux ...

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 5,12-dihydro-5-phenyl indole (3,2-a)carbazole production method and belongs to the field of organic chemical synthesis. The 5,12-dihydro-5-phenyl indole (3,2-a)carbazole is synthesized by the following steps of utilizing 4-amino-N-phenyl carbazole as a beginning raw material, brominating and Suzuki and Buchwald coupling. The synthesizing method ahs the advantages of little side reaction in a reaction process, simpleness in operation and high yield. The synthesizing 5,12-dihydro-5-phenyl indole (3,2-a)carbazole can be applied to the fields of organic photoelectric materials, medicine and the like and is an important intermediate of carbazole photoelectric materials, medicine and pesticides.

Description

technical field [0001] The present invention relates to a preparation method of a class of indolo[3,2-a]carbazole derivatives, in particular to a 5,12-dihydro-5-phenylindolo[3,2-a]carbazole The synthetic method belongs to the field of organic chemical synthesis. Background technique [0002] Carbazole is an important heterocyclic compound, which widely exists in natural products and medicinal chemical molecules, and has obvious biological and pharmacological activities. In addition, carbazole and its derivatives have excellent light spot properties, which have a large π-electron conjugated system and strong intramolecular electron transfer characteristics. From the structural point of view, the electrophilic N atom of carbazole is induced by the Absorb the electrons on the double bond; on the other hand, due to the p-π conjugation effect, the unshared electrons of the N atom donate to the double bond, making the double bond rich in electrons. Therefore, carbazole derivativ...

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): C07D487/04
Inventor 杨振强孙敏青屈凤波马欣李奎杨瑞娜樊燕鸽席振峰
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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