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 m

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

Example Embodiment

[0030] Example 1

[0031]

[0032] In a 10mL reaction flask, sequentially 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 for 8h at 80°C. After the reaction is complete, pour the reaction solution into a separatory funnel, and add 10 mL of saturated sodium bicarbonate aqueous solution to it, shake, stand still, separate the oil and water phase, extract the water phase with dichloromethane (2×5 mL), and separate the organic phase. After mixing the organic phase, dry with anhydrous sodium sulfate and filter. The volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (the eluent was dichloromethane) to obtain a yellow solid as the target product (1a) (90 mg, yield 70%). The target product was confirmed by nuclear magnetic resonance spectr...

Example Embodiment

[0033] Example 2

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

Example Embodiment

[0035] Example 3

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

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 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