A One Step Synthesis Of Polyfunctional Quinoline Using Heterogeneous Silica Chloride As Catalyst Under Sonic Condition
Sudha. S, Bandita Datta, Pasha. M. A
Index Terms: 2-aminoaryl ketones, 1,3-diketones, room temperature reaction, polyfunctional Quinoline, Silica Chloride, solvent-free reaction and Ultrasound.
Abstract: A simple, rapid and efficient method for the preparation of polyfunctional quinoline derivatives by the reaction of 2-aminobenzophenone with ketones or 1,3-diketones in the presence of silica chloride under heterogeneous, solvent-free and sonic condition is reported. The significant features of this method are short reaction times, high yields of the products, mild reaction condition, solvent-free reaction, economy, non-toxicity and reusability of the catalyst.
 J.P. Michael, Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. Vol. 25, pp. 166-187, 2008 and previous reviews of this series
 V.V. Kouznetsov, L.Y.V. Mendez, C.M.M. Gomez, Recent progress in the synthesis of quinolines. Curr. Org. Chem. Vol. 9, pp. 141-161, 2005
 J.P. Michael, Indolizidine and quinolizidine alkaloids. Nat. Prod. Rep. Vol. 21, pp. 625-649 2004
 Y.-C. Wu, L. Liu, H.-J. Li, D. Wang, Y.-J. Chen, Skraup−Doebner−Von Miller Quinoline Synthesis Revisited: Reversal of the Regiochemistry for γ-Aryl-β,γ-unsaturated α-Ketoesters. J. Org. Chem. Vol. 71, pp. 6592-95, 2006
 S.E. Denmark, S. Venkatraman, On the Mechanism of the Skraup-Doebner-Von Miller Quinoline Synthesis J. Org. Chem. Vol. 71, pp.1668-1676, 2006
 L.W. Deady, S.M. Devine, Novel annulated products from aminonaphthyridinones. Tetrahedron Vol. 62, pp. 2313-2320, 2006.
 R. Martinez, D.J. Ram_on, M. Yus, A direct reaction between 2-aminobenzylic alcohol derivatives and either ketones or alcohols in the presence of a base and benzophenone as hydride scavenger allows the synthesis of polysubstituted quinolines without any transition-metal catalyst. J. Org. Chem. Vol. 73, pp. 9778-80, 2008.
 E.A. Fehnel, Friedländer syntheses with o-aminoaryl ketones. III. Acid-catalyzed condensations of o-aminobenzophenone with polyfunctional carbonyl compounds. J. Heterocycl. Chem. Vol. 4, pp. 565-570, 1967.
 Y.Z. Hu, G. Zang, R.P. Thummel, Friedländer approach for the incorporation of 6-bromoquinoline into novel chelating ligands. Org. Lett. Vol. 5, pp. 2251-53, 2003
 A. Arcadi, M. Chiarini, S.D. Giuseppe, F. Marinelli, A New Green Approach to the Friedländer Synthesis of Quinolines. Synlett Vol. 2, pp. 203-7, 2003.
 D.S. Bose, R.K. Kumar, An efficient, high yielding protocol for the synthesis of functionalized quinolines via the tandem addition/annulation reaction of o-aminoaryl ketones with alphamethylene ketones.Tetrahedron Lett. Vol. 47, pp. 813-816, 2006
 J. Wu, H.G. Xia, K .Gao, Molecular iodine: a highly efficient catalyst in the synthesis of quinolines viaFriedländer annulation. Org. Biomol. Chem. Vol. 4. pp. 126-127, 2006.
 D. Bandita, M.A. Pasha, Silica chloride catalyzed efficient route to novel 1-amidoalkyl-2-naphthylamines under sonic condition in water Ultrason. Sonochem. Vol. 20, pp. 303-307, 2013
 S. Nagashree, M.A. Pasha, Ni(NO3)2•6H2O/I2/water: A new, mild and efficient system for the selective oxidation of alcohols into aldehydes and ketones under sonic condition. Ultrason. Sonochem. Vol. 20, pp. 810-814, 2013
 Sudha, S.; M.A. Pasha, Ultrasound assisted synthesis of tetrahydrobenzo[c]xanthene-11-ones using CAN as catalyst Ultrason. Sonochem. Vol. 19, pp. 994-998, 2012
 D. Bandita, M.A. Pasha, Glycine catalyzed convenient synthesis of 2-amino-4H-chromenes in aqueous medium under sonic condition. Ultrason. Sonochem. Vol. 19, pp. 725-728, 2012.
 K. Wilson, J.H. Clark, Synthesis of a novel supported solid acid BF3 catalyst. Chem. Commun., 1998, 19, 2135-2137
 A.L. Kennedy, A.M. Fryer, J.A. Josey, A new resin-bound universal isonitrile for the Ugi 4CC reaction: preparation and applications to the synthesis of 2,5- diketopiperazines and 1,4 benzodiazepine-2,5-diones. Org. Lett., Vol. 4, pp. 1167-70, 2002
 J.L. Luche, A few questions on the sonochemistry of solutions. Ultrason. Sonochem. Vol. 4, pp. 211-15, 1997
 Mason T.J. Ultrasound in synthetic organic chemistry. Chem. Soc. Rev., Vol. 26, pp. 443-451, 1997.
 N.K. Hitendra, S. Manisha, M.P. Kaushik, Synthesis of 4-Aryl Substituted 3,4-Dihydropyrimidinones Using Silica-chloride Under Solvent Free Conditions Molecules Vol. 12, pp. 1341-51, 2007.