Bicyclic 1,2,3-Triazolium Ionic Liquids: Synthesis, Characterization, and Application to Rutaecarpine Synthesis

Starting with commercial reagents, bicyclic 1,2,3-triazolium ionic liquids [b-3C-tr][NTf2] (1) and [b-4C-tr][NTf2] (2) were synthesized in four steps with high overall isolated yields of 68% and 76%, respectively. Since the C-5 hydrogen is acidic, under basic condition ionic liquids 1 and 2 were rea...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2011-08, Vol.13 (16), p.4434-4437
Main Authors: Tseng, Ming-Chung, Cheng, Hui-Ting, Shen, Meng-Jane, Chu, Yen-Ho
Format: Article
Language:English
Subjects:
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Ionic Liquids - chemistry
Molecular Structure
Quinazolines - chemical synthesis
Quinazolines - chemistry
Triazoles - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Starting with commercial reagents, bicyclic 1,2,3-triazolium ionic liquids [b-3C-tr][NTf2] (1) and [b-4C-tr][NTf2] (2) were synthesized in four steps with high overall isolated yields of 68% and 76%, respectively. Since the C-5 hydrogen is acidic, under basic condition ionic liquids 1 and 2 were readily methylated with methyl iodide to afford chemically stable ionic liquids 7 and 8 at room temperature (88% and 82%, respectively). Ionic liquid 1 was used as the ionic solvent to demonstrate its usefulness for the synthesis of rutaecarpine, a natural product.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201793v