Ionic liquid-promoted regiospecific Friedlander annulation: novel synthesis of quinolines and fused polycyclic quinolines.
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.
Palimkar
Sanjay S
SS
Division of Organic Chemistry, Technology, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India.
Siddiqui
Shapi A
SA
Daniel
Thomas
T
Lahoti
Rajgopal J
RJ
Srinivasan
Kumar V
KV
D000838:Anions / Q000737:chemistry*; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007093:Imidazoles / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013997:Time Factors
D000838:Anions; D006571:Heterocyclic Compounds; D007093:Imidazoles; D011804:Quinolines