Phosphotungstic acid: An efficient, cost-effective and recyclable catalyst for the synthesis of polysubstituted quinolines

Molecules

Volumn 14, Issue 3, 2009, Pages 1126-1133

  Dabiri, Minoo ^a   Bashiribod, Sahareh ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Friedl nder annelation; Heterogeneous catalysis; Heteropolyacid; Quinoline.

Indexed keywords

PHOSPHOTUNGSTIC ACID; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; COST BENEFIT ANALYSIS; ENVIRONMENTAL PROTECTION; SYNTHESIS;

CATALYSIS; CONSERVATION OF NATURAL RESOURCES; COST-BENEFIT ANALYSIS; PHOSPHOTUNGSTIC ACID; QUINOLINES;

EID: 63449111648     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14031126     Document Type: Article

References (33)

1. Clark, J.H. Solid acids for green chemistry. Acc. Chem. Res. 2002, 35, 791-797.
2. Kozhevnikov, I.V. Catalysis by heteropoly acids and multicomponent polyoxometalates in liquidphase reactions. Chem. Rev. 1998, 98, 171-198, and references cited therein.
3. Firouzabadi, H.; Jafari, A.A. Heteropoly acids, their salts and polyoxometalates as heterogenous, efficient and eco-friendly catalysts in organic reactions: Some recent advances. J. Iran. Chem. Soc. 2005, 2, 85-114.
4. 2 as efficient, costeffective and recyclable catalytic system for the synthesis of highly substituted pyrroles. J. Mol. Catal. A: Chem. 2007, 278, 42-46.
5. Tsukuda, E.; Sato, S.; Takahashi, R.; Sodesawa, T. Production of acrolein from glycerol over silica-supported heteropoly acids. Catal. Commun. 2007, 8, 1349-1353.
6. Azizi, N.; Torkian, L.; Saidi, M.R. Highly efficient synthesis of bis(indolyl)methanes in water. J. Mol. Catal. A Chem. 2007, 275, 109-112.
7. Azizi, N.; Torkiyan, L.; Saidi, M.R. Highly efficient one-pot three-component Mannich reaction in water catalyzed by heteropoly acids. Org. Lett. 2006, 8, 2079-2082.
8. Kumar, A.; Singh, P.; Kumar, S.; Chandra, R.; Mozumdar, S. A facile one-pot synthesis of thioethers using heteropoly acids. J. Mol. Catal. A Chem. 2007, 276, 95-101.
9. Chen, Y.L.; Fang, K.C.; Sheu, J.Y.; Hsu, S.L.; Tzeng, C.C. Synthesis and antibacterial evaluation of certain quinolone derivatives. J. Med. Chem. 2001, 44, 2374-2377.
10. Roma, G.; Braccio, M.D.; Grossi, G.; Chia, M. 1,8-naphthyridines IV. 9-substituted N,N-dialkyl- 5-(alkylamino or cycloalkylamino) [1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides, new compounds with anti-aggressive and potent anti-inflammatory activities Eur. J. Med. Chem. 2000, 35, 1021.
11. Billker, O.; Lindo, V.; Panico, M.; Etiene, A.E.; Paxton, T.; Dell, A.; Rogers, M.; Sinden, R.E.; Morris, H.R. Identification of xanthurenic acid as the putative inducer of malaria development in the mosquito. Nature 1998, 392, 289-292.
12. Kouznetsov, V.V.; Mendez, L.Y.V.; Gomez, C.M.M. Recent progress in the synthesis of quinolines. Curr. Org. Chem. 2005, 9, 141-161.
13. Das, B.; Damodar, K.; Chowdhury, N.; Kumar, R.A. Application of heterogeneous solid acid catalysts for Friedlander synthesis of quinolines. J. Mol. Catal. A Chem. 2007, 274, 148-152.
14. Zolfigol, M.A.; Salehi, P.; Ghaderi, A.; Shiri, M. A catalytic and green procedure for Friedlander quinoline synthesis in aqueous media. Catal. Commun. 2007, 8, 1214-1218.
15. Narasimhulu, M.; Reddy, T.S.; Mahesh, K.C.; Prabhakar, P.; Rao, C.B.; Venkateswarlu, Y. Silica supported perchloric acid: A mild and highly efficient heterogeneous catalyst for the synthesis of poly-substituted quinolines via Friedlander hetero-annulation. J. Mol. Catal. A: Chem. 2007, 266, 114-117.
16. Zolfigol, M.A.; Salehi, P.; Ghaderi, A.; Shiri, M.; Tanbakouchian, Z. An eco-friendly procedure for the synthesis of polysubstituted quinolines under aqueous media. J. Mol. Catal. A Chem. 2006, 259, 253-258.
17. Zhang, L.; Wu, J. Friedländer Synthesis of Quinolines Using a Lewis Acid-Surfactant-Combined Catalyst in Water. Adv. Synth. Catal. 2007, 349, 1047-1051.
18. Bose, D.S.; Kumar, R.K. 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. 2006, 47, 813-816.
19. Atechian, S.; Nock, N.; Norcross, R.D.; Ratni, H.; Thomas, A.W.; Verron, J.; Masciadri, R. New vistas in quinoline synthesis. Tetrahedron 2007, 63, 2811-2823.
20. Wang, G.-W.; Jia, C.-S.; Dong, Y.-W. Benign and highly efficient synthesis of quinolines from 2-aminoarylketone or 2-aminoarylaldehyde and carbonyl compounds mediated by hydrochloric acid in water. Tetrahedron Lett. 2006, 47, 1059-1063.
21. Yadav, J.S.; Rao, P.P.; Sreenu, D.; Rao, R.S.; Kumar, V.N.; Nagaiah, K.; Prasad, A.R. Sulfamic acid: an efficient, cost-effective and recyclable solid acid catalyst for the Friedlander quinoline synthesis. Tetrahedron Lett. 2005, 46, 7249-7253.
22. Dabiri, M.; Baghbanzadeh, M.; Nikcheh, M.S. Oxalic acid: An efficient and cost-effective organic catalyst for the Friedlander quinoline synthesis under solvent-free conditions. Monatsh. Chem. 2007, 138, 1249-1252.
23. Yadav, J.S.; Reddy, B.V.S.; Sreedhar, P.; Srinivasa Rao, R.; Nagaiah, K. Silver phosphotungstate: A novel and recyclable heteropoly acid for Friedländer quinoline synthesis. Synthesis 2004, 2381-2385.
24. Dabiri, M.; Baghbanzadeh, M.; Nikcheh, M.S. Oxalic acid: An efficient and cost-effective organic catalyst for the Friedlander quinoline synthesis under solvent-free conditions. Monatsh. Chem. 2007, 138, 1249-1252.
25. Shaabani, A.; Rahmati, A.; Badri, Z. Sulfonated cellulose and starch: New biodegradable and renewable solid acid catalysts for efficient synthesis of quinolines. Catal. Commun. 2008, 9, 13-16.
26. Dabiri, M.; Baghbanzadeh, M.; Arzroomchilar, E. 1-methylimidazolium triflouroacetate ([Hmim]TFA): An efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxooctahydroxanthenes and 1,8-dioxo-decahydroacridines. Catal. Commun. 2008, 9, 939-942.
27. Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Zolfigol, M.A.; Agheb, M.; Heydari, S. Silica sulfuric acid: An efficient reusable heterogeneous catalyst for the synthesis of 2,3-dihydroquinazolin- 4(1H)-ones in water and under solvent-free conditions. Catal. Commun. 2008, 9, 785-788.
28. Salehi, P.; Dabiri, M.; Zolfigol, M.A.; Otokesh, S.; Baghbanzadeh, M. Selective synthesis of 2- aryl-1-arylmethyl-1H-1,3-benzimidazoles in water at ambient temperature. Tetrahedron Lett. 2006, 47, 2557-2560.
29. Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Shakouri, M.; Otokesh, S.; Ekrami, T.; Doosti, R. Efficient and eco-friendly synthesis of dihydropyrimidinones, bis(indolyl) methanes, and N-alkyl and N-arylimides in ionic liquids. J. Iran. Chem. Soc. 2007, 4, 393-401.
30. Misono, M. Unique acid catalysis of heteropoly compounds (heteropolyoxometalates) in the solid state. Chem. Commun. 2001, 1141-1152.
31. n (M=Al, Mg, Ca) under solvent-free conditions. Heterocycles 2008, 75, 2513-2521.
32. Waldmann, H.; Karunakar, G.V.; Kumar, K. Gold(III)-mediated aldol condensations provide efficient access to nitrogen heterocycles. Org. Lett. 2008, 10, 2159-2162.
33. 4 catalyzes the solvent-free indirect Friedländer synthesis of polysubstituted quinolines from alcohols. Eur. J. Org. Chem. 2007, 1599-1605.