B. Maleki, Esmail Rezaei Seresht, Z. Ebrahimi
Mar 4, 2015
Citations
0
Influential Citations
44
Citations
Journal
Organic Preparations and Procedures International
Abstract
Quinolines and their derivatives are very important biologically and occur widely in natural products. Members of this family have displayed interesting physiological activities and found major applications in medicinal chemistry, as anti-malarial, anti-bacterial, anti-inflammatory, anti-hypertensive, anti-platelet, and tyrosine kinase inhibiting agents. They are also useful for the preparation of nanoand meso-structures having enhanced electronic and photonic properties. Moreover, quinolines are also employed in the fields of bioorganic, bioorganometallic processes and industrial organic chemistriy. Therefore, the exploration of efficient synthetic methods to construct the quinoline framework has continually drawn great attention for many decades. Among these methods, the Friedlander annulations is one of the simplest and most direct approaches for the synthesis of quinolines. It involves the acid-, base-catalyzed or thermal condensation between o-aminoarylketones and aldehydes with another carbonyl compound possessing a reactive a-methylene group followed by cyclodehydration. It has been shown that acid catalysis is more effective than base catalysts for the Friedlander annulation. In recent years, Bronsted and Lewis acids such as ionic liquids, sulfamic acid, hydrochloric acid, zirconium tetrakisdodecyl sulfate [Zr(DS)4], 29 silica sulfuric acid, silica supported phosphomolybdic acid [PMA.SiO2], 32 nanocrystalline aluminium oxide, dodecylphosphonic acid (DPA), poly(N-bromoethylbenzene-1,3-disulfonamide) [PBBS] or N,N,N0,N0-tetrabromobenzene-1,3-disulfonamide [TBBDA], zinc triflate, nano-flake ZnO, CsxH3¡xPW12O40 heteropoly salts, Yb(OTf)3, nanosized MCM-41 supported ionic liquid [(BSPY)HSO4/MCM-41], 40 o-benzendisulfonimide and nanocrystalline sulfated zirconia have been utilized. However, many of these methods suffer from harsh reaction conditions, long reaction times, low yields, expensive reagents, tedious work-up procedures. The main disadvantage of nearly all existing methods is that the catalysts cannot be recovered and reused. For these reasons, the use of solid and heterogeneous catalysts has received considerable attention in organic synthesis. This extensive application of heterogeneous catalysts can make the process more efficient from both the environmental and economic points of view when the catalyst can be easily recycled. There are no previous report describing the use of Poly(AMPS-co-AA) in organic transformations. and it has been shown to possess several advantages such as low toxicity and cost, ease of handling and high catalytic activity as a potential green catalyst.