Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Indium Modified Mesoporous Zeolite AlMCM-41 as a Heterogeneous Catalyst for the Knoevenagel Condensation Reaction

  • Katkar, Santosh S. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Lande, Machhindra K. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Arbad, Balasaheb R. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Rathod, Sandip B. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
  • Received : 2010.02.10
  • Accepted : 2010.03.12
  • Published : 2010.05.20
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Abstract

The Indium modified mesoporous zeolite AlMCM-41 were synthesized by hydrothermal method and characterized by powder X-ray diffraction (XRD), fourier transform infrared spectroscopy (FT-IR) and scanning electron microscopy with energy dispersive spectroscopy (SEM-EDS) techniques. The Knoevenagel condensation of aldehyde with malononitrile or ethyl cyanoacetate was carried out at reflux condition in ethanol by using heterogeneous In/AlMCM-41 catalyst. This method is fast, efficient, easy work-up and eco-friendly to afford the corresponding Knoevenagel adducts. The catalyst was recovered and reused for several cycles with consistent activity.

Keywords

References

  1. Jones, G. Org. React. 1967, 15, 204.
  2. Lai, S. M.; Ng, C. P.; Martin-Aranda, R.; Yeung, K. L. Micropor. Mesopor. Mater. 2003, 66, 239. https://doi.org/10.1016/j.micromeso.2003.09.014
  3. Tietze, L. F.; Beifuss, U. Comprehensive Organic Synthesis 1991, 2, 341.
  4. Meuly, W. C.; Othmer, K. Encyclopedia of Chemical Technology, 3rd ed.; John Wiley & Sons: New York, 1979; Vol. 7, p 196.
  5. Bigi, F.; Chesini, L.; Maggi, R.; Sartori, G. J. Org. Chem. 1999, 64, 1033. https://doi.org/10.1021/jo981794r
  6. Lakshmi, K. M.; Ravindra, A.; Venkat R., Ch.; Sreedhar, B.; Choudary, B. M. Adv. Synth. Catal. 2006, 348, 569. https://doi.org/10.1002/adsc.200505266
  7. Lakshmi, K. M.; Choudary, B. M.; Venkat R., Ch.; Koteswara, R. K.; Figueras, F. Chem. Commun. 1998, 1033.
  8. Su, C.; Chen, Z. C.; Zheng, Q. G. Synthesis 2003, 555.
  9. Jones, G. Organic Reactions; Wiley: New York, 1967; Vol 15, p 204.
  10. Allen, C. F. H.; Spangler, F. W. Org. Synth. Coll. 1955, Vol. III, 377.
  11. Bose, D. S.; Narsaiah, A. V. J. Chem. Res (S) 2001, 36.
  12. Cragoe, E. J., Jr.; Robb, C. M.; Spragne, J. M. J. Org. Chem. 1950, 15, 381. https://doi.org/10.1021/jo01148a024
  13. Jin, T. S.; Wang, A. Q.; Shi, F.; Han, L. S.; Liu, L. B.; Li, T. S. Arkivoc 2006, (xiv), 78.
  14. Bastus, J. B. Tetrahedron Lett. 1963, 6, 955.
  15. Narsaiah, A. V.; Basak, A. K.; Visali, B.; Nagaiah, K. Synth. Commun. 2004, 34, 2893. https://doi.org/10.1081/SCC-200026625
  16. Cardillo, G.; Fabbroni, S.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Synth. Commun. 2003, 33, 1587. https://doi.org/10.1081/SCC-120018782
  17. Acker, D. S.; Hertler, W. R. J. Am. Chem. Soc. 1962, 84, 3370. https://doi.org/10.1021/ja00876a028
  18. Junjie, H.; Yanfen, X.; Yingpeng, Su.; Xuegong, S.; Xinfu, P. Catal. Comm. 2008, 9, 2077. https://doi.org/10.1016/j.catcom.2008.04.006
  19. Lehnert, W. Tetrahedron 1974, 30, 301. https://doi.org/10.1016/S0040-4020(01)91461-9
  20. Green, B.; Crane, R. I.; Khaidem, I. S.; Leighton, R. S.; Newaz, S. S.; Smyser, T. E. J. Org. Chem. 1985, 50, 640. https://doi.org/10.1021/jo00205a016
  21. Shanthan, R. P.; Venkataratnam, R. V. Tetrahedron Lett. 1991, 32, 5821. https://doi.org/10.1016/S0040-4039(00)93564-0
  22. Kumbhare, R. M.; Sridhar, M. Catal. Comm. 2008, 9, 403. https://doi.org/10.1016/j.catcom.2007.07.027
  23. Pullabhotla, R. V. S. R.; Rahman, A.; Jonnalagadda, S. B. Catal. Comm. 2009, 10, 365. https://doi.org/10.1016/j.catcom.2008.09.021
  24. Bartoli, G.; Beleggia, R.; Giuli, S.; Giuliani, A.; Marcantoni, E.; Massaccesi, M.; Paletti, M. Tetrahedron Lett. 2006, 47, 6501. https://doi.org/10.1016/j.tetlet.2006.07.031
  25. Kantevari, S.; Bantu, R.; Nagarapu, L. J. Mol. Catal. A Chem. 2007, 269, 53. https://doi.org/10.1016/j.molcata.2006.12.039
  26. Gupta, R.; Gupta, M.; Paul, S.; Gupta, R. Bull. Korean. Chem. Soc. 2009, 30, 2419. https://doi.org/10.5012/bkcs.2009.30.10.2419
  27. Smith, K. Solids Supports and Catalysts in Organic Synthesis; Ellis Horwood: Chichester, 1992.
  28. Choudhary, V. R.; Jana, S. K.; Kiran, B. P. Catal. Lett. 2000, 64, 223. https://doi.org/10.1023/A:1019084314356
  29. Choudhary, V. R.; Jana, S. K.; Patil, N. S. Catal. Lett. 2001, 76, 235. https://doi.org/10.1023/A:1012313726908
  30. Choudhary, V. R.; Jana, S. K.; Patil, N. S. Tetrahedron Lett. 2002, 43, 1105. https://doi.org/10.1016/S0040-4039(01)02335-8
  31. Katkar, S. S.; Mohite, P. H.; Gadekar, L. S.; Vidhate, K. N.; Lande, M. K. Chin. Chem. Lett. 2010, 21, 421. https://doi.org/10.1016/j.cclet.2009.10.020
  32. Katkar, S. S.; Mohite, P. H.; Gadekar, L. S.; Arbad, B. R.; Lande, M. K. Centr. Eur. J. Chem. 2010, 8, 320. https://doi.org/10.2478/s11532-009-0151-7
  33. Katkar, S. S.; Arbad, B. R.; Lande, M. K. Arab J. Sci. Eng. 2009, Accepted.
  34. Shinde, S. V.; Jadhav, W. N.; Lande, M. K.; Gadekar, L. S.; Arbad, B. R.; Kondre, J. M.; Karade, N. N. Catal. Lett. 2008, 125, 57 https://doi.org/10.1007/s10562-008-9508-3
  35. Gadekar, L. S.; Mane, S. R.; Katkar, S. S.; Arbad, B. R.; Lande, M. K. Centr. Eur. J. Chem. 2009, 7, 550. https://doi.org/10.2478/s11532-009-0050-y
  36. Gadekar, L. S.; Katkar, S. S.; Mane, S. R.; Arbad, B. R.; Lande, M. K. Bull. Korean. Chem. Soc. 2009, 30, 2534.
  37. Pourahmad, A.; Sohrabnezhad, S.; Sadjadi, M. S.; Zare, K. Mater. Lett. 2008, 62, 655. https://doi.org/10.1016/j.matlet.2007.06.027

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