Nickel nanoparticle-catalyzed facile and efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation under solvent-free conditions

Tetrahedron Letters

Volumn 50, Issue 15, 2009, Pages 1754-1756

  Sapkal, Suryakant B ^a   Shelke, Kiran F ^a   Shingate, Bapurao B ^a   Shingare, Murlidhar S ^a  

^a DR BABASAHEB AMBEDKAR MARATHWADA UNIVERSITY   (India)

Author keywords

Green chemistry; Hantzsch condensation; Nanoparticle; Polyhydroquinoline derivative

Indexed keywords

NANOPARTICLE; NICKEL; ORGANIC SOLVENT; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; HANTZSCH CONDENSATION; ONE POT SYNTHESIS; PARTICLE SIZE; POLYMERIZATION; PURIFICATION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; SURFACE PROPERTY;

EID: 60649101872     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.140     Document Type: Article

References (32)

1. Saxena A., Kumar A., and Mujumdar S. J. Mol. Catal. A: Chem. 269 (2007) 35
2. Alonso F., Riente P., and Yus M. Tetrahedron 64 (2008) 1847
3. Alonso F., Riente P., and Yus M. Tetrahedron Lett. 49 (2008) 1939
4. Alonso F., Riente P., and Yus M. Synlett (2008) 1289
5. Dhakshinamoorty A., and Pitchumani K. Tetrahedron Lett. 49 (2008) 1818
6. Zank L., and Zielinski J. Appl. Catal. A: Gen. 334 (2008) 268
7. Mannhold R., Jablonka B., Voigdt W., Schoenafinger K., and Schravan K. Eur. J. Med. Chem. 27 (1992) 229
8. Bossert F., Meyer H., and Wehinger. Angew. Chem., Int. Ed. Engl. 20 (1981) 762
9. Nakayama H., and Kasoaka Y. Heterocycles 42 (1996) 901
10. Klusa V. Drugs Future 20 (1995) 135
11. Bretzel R.G., Bollen C.C., Maeser E., and Federlin K.F. Am. J. Kidney Dis. 21 (1993) 53
12. Bretzel R.G., Bollen C.C., Maeser E., and Federlin K.F. Drugs Future 17 (1992) 465
13. Boer R., and Gekeler V. Drugs Future 20 (1995) 499
14. Sainani J.B., and Shah A.C. Indian J. Chem., Sect. B 33 (1994) 526
15. Sufirez M., Ochoa E., Verdecia Y., Verdecia B., Moran L., Martin N., Quinteiro M., Seoane C., Soto J.L., Novoa H., Blaton N., and Peters O.M. Tetrahedron 55 (1999) 875
16. Li M., Zuo Z., Wen L., and Wang S. J. Comb. Chem. 10 (2008) 436
17. Tu S.J., Zhou J.F., Deng X., Cai P.J., Wang H., and Feng J.C. Chin. J. Org. Chem. 21 (2001) 313
18. Sabitha G., Reddy G.S.K., Reddy C.S., and Yadav J.S. Tetrahedron Lett. 44 (2003) 4129
19. Ji S.J., Jiang Z.Q., Lu J., and Loa T.P. Synlett (2004) 831
20. Zhang X.Y., Li Y.Z., Fan X.S., Qu G.R., Hu X.Y., and Wang J. J. Chin. Chem. Lett. 17 (2006) 150
21. Maheswara M., Siddaiah V., Damu G.L., and Venkata Rao C. Arkivoc 2 (2006) 201
22. Das B., Ravikanth B., Ramu R., and Vittal Rao B. Chem. Pharm. Bull. 54 (2006) 1044
23. Song G., Wang B., Wu X., Kang Y., and Yang L. Synth. Commun. 35 (2005) 2875
24. Reddy C.S., and Raghu M. Chin. Chem. Lett. 19 (2008) 775
25. Adibi H., Samimi H.A., and Beygzadeh M. Catal. Commun. 8 (2007) 2119
26. Heravi M.M., Bakhtiri K., Javadi N.M., Bamoharram F.F., Saeedi M., and Oskooi H.A. J. Mol. Catal. A: Chem. 264 (2007) 50
27. Donelson J.L., Gibbs A., and De S.K. J. Mol. Catal. A: Chem. 256 (2006) 309
28. Cherkupally S.R., and Mekalan R. Chem. Pharm. Bull. 56 (2008) 1002
29. 4 solution was adjusted to 13 by adding an ammonia solution with continuous stirring. The reaction mixture was refluxed at 70 °C for one hour till the final color of the solution became black. The growth of Ni nanoparticles was completed after 1 h. The particle size and structure of the resultant Ni nanoparticles have been characterized by X-ray diffraction (XRD), transmittance electron microscopy (TEM), and energy dispersive X-ray (EDX) analysis.
30. Chen D.H., and Wu S.H. Chem. Mater. 12 (2000) 1354
31. Synthesis of polyhydroquinoline derivatives: A mixture of aromatic aldehyde (1 mmol), dimedone (1 mmol), ammonium acetate (1.5 mmol), ethyl acetoacetate (1 mmol), and Ni nanoparticle (10 mol %) which was taken in a Borosil beaker. The reaction mixture was homogenized with the help of a glass rod and irradiated in a microwave oven (540 W) by intervals of 5 s. The progress of the reaction was checked on TLC. After completion, the reaction mixture was cooled at room temperature. Then, it was extracted with ethyl acetate; the organic layer was dried over sodium sulphate and concentrated in a vacuum to afford the crude products. The pure products were obtained by recrystallization from ethanol. Nanoparticles were recovered by centrifuging the aqueous layer and reutilized four times for the same reaction (Table 2).
32. Hou Y., Kondoh H., Ohta T., and Gao S. Appl. Surf. Sci. 241 (2005) 218