Chitosan-SO3H is found to catalyze the Friedländer condensation/annulation reaction of 2-aminoaryl ketones with α-methyleneketones to produce the corresponding quinolinederivatives in high yields in short reaction times. The use of recyclable and biodegradable chitosan-SO3H makes this method quite simple, more convenient, and economically viable compared to acid catalyzed methods reported in the literature
Ionic Liquid-Promoted Regiospecific Friedlander Annulation: Novel Synthesis of Quinolines and Fused Polycyclic Quinolines
作者:Sanjay S. Palimkar、Shapi A. Siddiqui、Thomas Daniel、Rajgopal. J. Lahoti、Kumar V. Srinivasan
DOI:10.1021/jo035153u
日期:2003.11.1
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
Homogeneous catalysis, heterogeneous recycling: a new family of branched molecules with hydrocarbon or fluorocarbon chains for the Friedländer synthesis of quinoline under solvent-free conditions
作者:Lei Fang、Jianjun Yu、Ying Liu、Anyin Wang、Limin Wang
DOI:10.1016/j.tet.2013.10.029
日期:2013.12
A new family of branched catalysts with hydrocarbon or fluorocarbon chains was used to catalyze Friedländer reaction between 2-aminoarylketones and α-methylene ketones under solvent-free conditions in good to excellent yields. The catalysts exhibit temperature-dependent solubility and such a thermomorphic character allows them to be recovered by filtration conveniently at room temperature and reused
(Bromodimethyl)sulfonium Bromide Catalyzed Solvent-Free Friedlander Synthesis of Substituted Quinolines
作者:R. Venkatesham、A. Manjula、B. Vittal Rao
DOI:10.1002/jhet.873
日期:2012.7
A simple and efficient (bromodimethyl)sulfoniumbromidecatalyzedsynthesis of quinolines, by condensation of α‐amino carbonyl, that is, 2‐aminobenzophenone and 2‐aminoacetophenone with α‐methylene containing carbonyl like 1,3‐dicarbonyls has been developed. The reaction is versatile, solvent‐free protocol for generation of structurally diverse quinolines.
Efficient and Rapid Friedlander Synthesis of Functionalized Quinolines Catalyzed by Neodymium(III) Nitrate Hexahydrate
作者:Srinivas Adapa、Ravi Varala、Ramu Enugala
DOI:10.1055/s-2006-950296
日期:2006.11
Friedlander synthesis of quinolines catalyzed by neodymium nitrate [Nd(NO 3 ) 3 ·6H 2 O, 5 mol%] in ethanol at room temperature was achieved in moderate to excellent yields (62-94%).