Ionic Liquid-Promoted Regiospecific Friedlander Annulation: Novel Synthesis of Quinolines and Fused Polycyclic Quinolines
The Journal of Organic Chemistry2003Vol. 68(24), pp. 9371–9378
Citations Over TimeTop 10% of 2003 papers
Abstract
Several room-temperature ionic liquids (ILs) based on 1-butylimidazolium salts with varying anions were synthesized and evaluated for the preparation of biologically active substituted quinolines and fused polycyclic quinolines using the Friedlander heteroannulation reaction. On screening, 1-butylimidazolium tetrafluoroborate [Hbim]BF4 was found to be the best ionic liquid for the heteroannulation reaction, and the reasons to this effect are well explained. The reactions proceed very well under relatively mild conditions without any added catalyst. The IL acts as a promoter for this regiospecific synthesis and can be recycled. By this green approach, various quinolines were prepared in excellent yields and purity and well-characterized.
Related Papers
- → Density and Viscosity Data for Mixtures of Ionic Liquids with a Common Anion(2014)94 cited
- → Densities and viscosities for ionic liquids mixtures containing [eOHmim][BF4], [bmim][BF4] and [bpy][BF4](2014)64 cited
- → 1‐Butyl‐3‐methylimidazolium Tetrafluoroborate ([Bmim]BF4) Ionic Liquid: A Novel and Recyclable Reaction Medium for the Synthesis of vic‐Diamines(2003)43 cited
- → Synthesis of Ionic Liquids [BMIM]BF<sub>4 </sub>and [BMIM]PF<sub>6</sub> under Microwave Irradiation by One-Pot(2012)2 cited
- Synthesis and Characterization of Alkyl Imidazolium-Based Ionic Liquids(2012)