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

2-(2-thienyl)imidazole[1,2-a]pyridine-3-nitrile group construction taking DMF and ammonium iodide as cyanation agents

A thienyl, ammonium iodide technology, applied in the fields of cell biology, medicine, and materials, can solve problems such as hidden safety hazards, environmental pollution, abnormal inconvenience in post-processing processes, etc., and achieve mild reaction conditions, novel synthesis methods, and cheap reaction reagents. easy-to-get effect

Inactive Publication Date: 2019-10-29
GUILIN UNIVERSITY OF TECHNOLOGY
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional cyanation reagents, such as sodium cyanide, potassium cyanide, copper cyanide, and zinc cyanide, often generate highly toxic hydrogen cyanide during the cyanation process, causing serious environmental pollution. The post-processing process is extremely inconvenient, and there is a great potential safety hazard

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
  • 2-(2-thienyl)imidazole[1,2-a]pyridine-3-nitrile group construction taking DMF and ammonium iodide as cyanation agents
  • 2-(2-thienyl)imidazole[1,2-a]pyridine-3-nitrile group construction taking DMF and ammonium iodide as cyanation agents
  • 2-(2-thienyl)imidazole[1,2-a]pyridine-3-nitrile group construction taking DMF and ammonium iodide as cyanation agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In a 25mL test tube, add 0.2 mmol of compound 2-(2-thienyl)imidazol[1,2-a]pyridine, 0.4 mmol of copper nitrate trihydrate, 0.4 mmol of ammonium iodide, 0.4 mmol of acetic acid, and add N , 2 ml of N-dimethylformamide (DMF) was used as a reaction solvent, covered with a balloon filled with oxygen, and stirred at 130 degrees Celsius. After TLC (thin-layer chromatography) detection, the reaction solution was cooled to room temperature, the balloon was removed, and unreacted oxygen was slowly vented. The reaction solution was filtered, the filtrate was evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the compound 2-(2-thienyl)imidazo[1,2-a]pyridine-3-carbonitrile, the yield of this step was 60% .

Embodiment 2

[0025] Add 0.2 mmol of compound 2-(2-thienyl)imidazol[1,2-a]pyridine, 0.4 mmol of copper acetate, 0.4 mmol of ammonium iodide, 0.4 mmol of acetic acid into a 25mL test tube, add N,N - Dimethylformamide (DMF) 2 milliliters is used as the reaction solvent, put on a balloon filled with oxygen, and stir at 130 degrees Celsius. After TLC (thin-layer chromatography) detection, the reaction solution was cooled to room temperature, the balloon was removed, and unreacted oxygen was slowly vented. The reaction solution was filtered, the filtrate was evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the compound 2-(2-thienyl)imidazo[1,2-a]pyridine-3-carbonitrile, the yield of this step was 7% .

Embodiment 3

[0027] In a 25mL test tube, add 0.2 mmol of compound 2-(2-thienyl)imidazol[1,2-a]pyridine, 0.4 mmol of copper bromide, 0.4 mmol of ammonium iodide, 0.4 mmol of acetic acid, add N, 2 ml of N-dimethylformamide (DMF) was used as a reaction solvent, covered with a balloon filled with oxygen, and stirred at 130 degrees Celsius. TLC (thin layer chromatography) tracking detection, no target product was detected.

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 novel method for 2-(2-thienyl)imidazole[1,2-a]pyridine-3-nitrile group construction in one step taking DMF(N,N-dimethyl formamide) and ammonium iodide as cyanation agents. According to the method, 2-(2-thienyl)imidazole[1,2-a]pyridine is taken as a reaction raw material, the DMF(N,N-dimethyl formamide) and the ammonium iodide are taken as the cyanation agents to construct2-(2-thienyl)imidazole[1,2-a]pyridine-3-nitrile group in one step. According to the method, the synthesis mode is novel, the reaction condition is mild, reaction agents are cheap and easy to obtain,the N,N-dimethyl formamide can be used as a reaction solvent, and can also serve as the cyanation agent to provide the carbon atom in the nitrile group, ammonium iodide provides the nitrogen atom in the nitrile group, a nitrile source by using the combination is safe and non-toxic, and the development requirements of green chemistry are met.

Description

technical field [0001] The invention belongs to the technical fields of medicine, materials, cell biology, etc., and specifically relates to a one-step construction of 2-(2-thienyl) using DMF (N,N-dimethylformamide) and ammonium iodide as cyanation reagents. ) A new method for imidazo[1,2-a]pyridine-3-carbonitriles. Background technique [0002] 2-(2-thienyl)imidazo[1,2-a]pyridine-3-carbonitrile compounds are a very important class of pharmaceutical intermediates, which can be used to synthesize various pharmaceutically active drug molecules. The contained structural skeleton can be used as the starting material to construct the familiar drug molecules sapiridan with antidepressant effect and necopiridan with anesthetic effect. Traditional cyanation reagents, such as sodium cyanide, potassium cyanide, copper cyanide, and zinc cyanide, often generate highly toxic hydrogen cyanide during the cyanation process, causing serious environmental pollution. It makes the post-proces...

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 Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 及方华王守才蒋光彬
Owner GUILIN UNIVERSITY OF TECHNOLOGY
Features
  • Generate Ideas
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com