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

Synthesis method of 3-(2-cyanovinyl)indole derivative

A technology of indole derivatives and cyanovinyl, applied in the direction of organic chemistry, can solve the problems of high toxicity and high price of diethyl phosphate compounds, and achieve the effects of low toxicity, simple operation, and cheap raw materials

Inactive Publication Date: 2018-10-02
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
View PDF2 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since 3-formyl indole derivatives are more expensive than corresponding indole derivatives, and diethyl phosphate compounds are more toxic, the above methods are contrary to the concept of molecular economy and environmental friendliness, which limits the application

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 3-(2-cyanovinyl)indole derivative
  • Synthesis method of 3-(2-cyanovinyl)indole derivative
  • Synthesis method of 3-(2-cyanovinyl)indole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] In a 10mL reaction flask, add 1-methyl-2-phenylindole (2a) (104mg, 0.5mmol), 3-dimethylaminoacrylonitrile (3) (48mg, 0.5mmol), p-toluenesulfonate Acid monohydrate (190mg, 1.0mmol), glacial acetic acid (600mg, 10.0mmol) and 2mL solvent dichloroethane were stirred at 80°C for 8h. After the reaction is completed, the reaction solution is poured into a separatory funnel, and 10 mL of saturated aqueous sodium bicarbonate solution is added thereto, shaken, left to stand, and the oil-water phase is separated, and the water phase is extracted with dichloromethane (2 × 5 mL), and the organic Mutually. The organic phases were mixed, dried over anhydrous sodium sulfate, and filtered. The volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (dichloromethane as the eluent) to obtain the target product (1a) (90 mg, yield 70%) as a yellow solid. The target product was confirmed by NMR and high-resolution mass spe...

Embodiment 2

[0034] The reaction steps and operations are the same as in Example 1, except that the reaction time is 24 hours. The reaction was stopped, and the target product 1a (89 mg, yield 69%) was obtained after post-processing.

Embodiment 3

[0036] The reaction steps and operations are the same as in Example 1, except that the reaction time is 4 hours. The reaction was stopped, and the target product 1a (44 mg, yield 34%) was obtained after post-processing.

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 3-(2-cyanovinyl)indole derivative. An indole derivative cheap, easy to obtain and having structural diversity is used as a raw material and performs continuous Friedel-Crafts reaction / elimination reaction with 3-dimethylamino acrylonitrile in the presence of acid, and the 3-(2-cyanovinyl)indole derivative is synthesized. Compared with a reported 3-(2-cyanovinyl)indole derivative synthesis method, the raw material is cheap, easy to obtain and low in toxicity, operation is easy and simple, the reaction conditions are mild, and the efficiency is high.

Description

technical field [0001] The present invention relates to a kind of indole derivative that is cheap and easy to get, has structural diversity as raw material and 3-dimethylaminoacrylonitrile to carry out continuous Friedel-Crafts reaction / elimination reaction in the presence of acid to synthesize 3-(2 - A method of cyanovinyl)indole derivatives. Compared with the reported synthetic methods of 3-(2-cyanovinyl)indole derivatives, the present invention has cheap and easy-to-obtain raw materials, low toxicity, simple operation, mild synthetic reaction conditions and high efficiency. Background technique [0002] 3-alkenylindole derivatives are an important class of N-heterocyclic compounds, and their potential biological activities have attracted widespread attention. 3-alkenyl indole derivatives can not only be used as anti-tumor, anti-inflammatory, anti-viral and other drugs, but also important intermediates for the synthesis of other biologically active indole derivatives. In...

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): C07D209/18
CPCC07D209/18
Inventor 吴凯凯余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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