RESEARCH ARTICLE

 

Solventless synthesis of quinoline derivatives: Acceleration of Friedländer reaction by supported heteropoly acids

 

 

Ezzat Rafiee^{I, II, *}; Fereshteh Khajooei Nejad^I; Mohammad Joshaghani^{I, II}

^IFaculty of Chemistry, Razi University, Kermanshah, 67149, Iran
^IIKermanshah Oil Refining Company, Kermanshah, Iran

 

 

---

ABSTRACT

Different Keggin type heteropoly acids (HPAs) and supported ones on solids with different nature and textural properties were used in the Friedländer reaction in order to obtain quinoline derivatives. This conversion has been preceded by tungstophosphoric acid supported on silica, KSF and activated carbon as optimized catalysts in high yields and short reaction times. The general applicability of this method is demonstrated by using various substrates including ketones, β-ketoesters and β-diketones. For most substrates the reaction worked well. These catalysts were found to be reusable and considerable catalytic activity could still be achieved after the fourth run.

Keywords: Friedländer reaction, quinoline derivatives, heteropoly compound, supported catalysts, solvent-free condition

---

 

 

Full text available only in pdf format.

 

Acknowledgements

We thank the Razi University Research Council and Kermanshah Oil Refining Company for support of this work.

 

References

1 S. Fetzner, Appl. Microbiol. Biotechnol., 1998, 49, 237-243.         [ Links ]

2 I. Murakami-Kubo, K. Doh-Ura, K. Ishikawa, S. Kawatake, K. Sasaki, J. Kira, S. Ohta and T. Iwaki, J. Virology, 2004, 78, 1281-1288.         [ Links ]

3 G. Roma, M.D. Braccio, G. Grossi, F. Mattioli and M. Ghia, Eur. J. Med. Chem., 2000, 35, 1021-1035.         [ Links ]

4 D. Doube, M. Blouin, C. Brideau, S. Desmarais, D. Eithier, J.P Fagueyret, R.W. Friesen, Y. Girard, J. Guay, P. Tagari and R.N. Young, Bioorg. Med. Chem. Lett, 1998, 8, 1255-1260.         [ Links ]

5 T.C. Ko, M.J.C. Hour, C.M. Teng K.H. Lee, S.C. Kuo and L. Huang, J. Bioorg. Med. Lett., 2001, 11, 279-282.         [ Links ]

6 I. Saito, S. Sando and K. Nakatani, Bioorg. Med. Chem., 2001, 9, 2381-2385.         [ Links ]

7 S.S. Palimkar, S.A. Siddiqui, T. Daniel, R.J. Lahoti and K.V. Srinivasan, J. Org. Chem., 2003, 68, 9371-9378.         [ Links ]

8 Z.H. Skraup, Monatsh. Chem, 1880, 1, 316-318.         [ Links ]

9 W. Pfitzinger, J. Prakt. Chem, 1886, 33, 100-105.         [ Links ]

10 R. Long and K. Schofield, J. Chem. Soc., 1953, 3161-3167.         [ Links ]

11 P. Friedlander, Chem. Berr, 1882, 15, 2572-2575.         [ Links ]

12 V.V. Kouznetsov, L.Y. Mendz and C.M.M. Gomez, Curr Org Chem., 2005, 9, 141-161.         [ Links ]

13 J. Wu, H.G. Xia and K. Gao, Org. Biomol. Chem., 2006, 4, 126-129.         [ Links ]

14 S.J. Song, S.J. Cho, D.K. Park, T.W. Kwan and S.A. Jenekhe, Tetrahedron Lett., 2003, 44, 255-257.         [ Links ]

15 A. Arcadi, M. Chiarini, S.D. Giuseppe and F. Marinelli, Synlett., 2003, 203-207.         [ Links ]

16 H. Eckert, Angew. Chem. Int. Ed. Engl., 1981, 20, 208-210.         [ Links ]

17 J.S. Yadav, P. Rao, D. Sreenu, R.S. Rao, V.N. Kumar, K. Nagaiah and A.R.Prasad, Tetrahedron Lett., 2005, 46, 7249-7253.         [ Links ]

18 M.M. Heravi, N.M. Haj, B. Baghernejad, Y.S. Beheshtiha and F.F. Bamoharram, E-J. Chem., 2010, 7, 875-881.         [ Links ]

19 M. Dabiri and S. Bashiribod, Molecules, 2009, 14, 1126-1133.         [ Links ]

20 Akbari, A. Heydari, H.R. Kalhor and S.A. Kohan, J. Comb. Chem, 2010, 12, 137-140.         [ Links ]

21 B. Das, M. Krishnaiah, K. Laxminarayana and D. Nandankumar, Chem. Pharm. Bull., 2008, 56, 1049-1051.         [ Links ]

22 S. Ghassamipour and A.R. Sardarian, Tetrahedron Lett., 2009, 50, 514-519.         [ Links ]

23 A. Kiss, A. Potor and Z. Hell, Catal. Lett., 2008, 125, 250-253.         [ Links ]

24 A.H. Li, D.J. Beard, H. Coate, A. Honda, M. Kadalbajoo, A. Kleinberg, R. Laufer, K.M. Mulvihill, A. Nigro, P. Rastogi, D. Sherman, K.W. Siu, A.G. Steinig, T. Wang, D. Werner, A.P. Crew and M.J. Mulvihill, Synthesis, 2010, 1678-1686.         [ Links ]

25 J.S. Yadav, B.V.S. Reddy, P. Sreedhar, P.S. Rao and K. Nagaiah, Synthesis, 2004, 2381-2385.         [ Links ]

26 X.L. Zhang, Q.Y. Wang, S.R. Sheng, Q. Wang and X.L. Liu, Synth. Commun., 2009, 39, 3293-3304.         [ Links ]

27 S. Kumar, A. Saini and J.S. Sandhu, Synth. Commun., 2007, 37, 4071-4078.         [ Links ]

28 G.W. Wang, C.S. Jia and Y.W. Dong, Tetrahedron Lett., 2006, 47, 1059-1063.         [ Links ]

29 M. Narasimhulu, T.S. Reddy, K.C. Mahesh, P. Prabhakar, C.B. Rao and Y. Venkateswarlu, J. Mol. Catal. A: Chem., 2007, 266, 114-117.         [ Links ]

30 D. Yang, K. Jiang, J. Li and F. Xu, Tetrahedron, 2007, 63, 7654-7658.         [ Links ]

31 M.A. Zolfigol,P. Salehi,A. GhaderiandM. Shiri, Catal. Commun, 2007, 8, 1214-1218.         [ Links ]

32 M.T. Pope, Heteropoly and Isopoly Oxometalates, Springer, Berlin, 1983.         [ Links ]

33 J.B. Moffat, Metal-Oxygen Clusters, The Surface and Catalytic Properties of Heteropoly Oxometalates, Kluwer, New York, 2001.         [ Links ]

34 E. Rafiee, F. Paknezhad, Sh. Shahebrahimi, M. Joshaghani, S. Eavani and S. Rashidzadeh, J. Mol. Catal. A: Chem, 2008, 282, 92-98.         [ Links ]

35 E. Rafiee, M. Joshaghani, S. Eavani and S. Rashidzadeh, Green Chem., 2008, 10, 982-989.         [ Links ]

36 U.V. Desai, S.D. Mitragotri, T.S. Thopate, D.M. Pore and P.P. Wadgaonkar, Arkivoc, 2006, 198-204.         [ Links ]

37 B. Das, K. Damodar, N. Chowdhury and R.A. Kumar, J. Mol. Catal. A: Chem., 2007, 274, 148-152.         [ Links ]

38 S. Sadjadi, S, Shiri, R. Hekmatshoar and Y.S. Beheshtiha, Monatsh. Chem., 2009, 140, 1343-1347.         [ Links ]

39 J. López-Sanz, E. Pérez-Mayoral, D, Procházková, R.M. Martín-Aranda and A.J. López-Peinado, Top. Catal., 2010, 53, 1430-1437.         [ Links ]

40 X.L. Zhang, Q.S. Hu, S.R. Sheng, C. Xiao and M.Z. Cai, J. Chinese Chem. Soc., 2011, 58, 18-23.         [ Links ]

41 M. Barbero, S. Bazzi, S. Cadamuro and S. Dughera, Tetrahedron Lett., 2010, 51, 2342-2344.         [ Links ]

 

 

Received 25 October 2010
Revised 23 March 2011
Accepted 27 March 2011

 

 

* To whom correspondence should be addressed. E-mail: ezzat_rafiee@yahoo.com; e.rafiei@razi.ac.ir