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Rapid and efficient one-pot synthesis of 1,4-dihydropyridine and polyhydroquinoline derivatives through the Hantzsch four component condensation by zinc oxide

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Abstract

A one-pot four-component reaction of aldehydes, ethyl acetoacetate/5,5-dimethyl-1,3-cyclohexanedione, ethyl acetoacetate and ammonium acetate in the presence of 10 mol% of ZnO as a heterogeneous catalyst for the synthesis of corresponding 1,4- dihydropyridine and polyhydroquinoline derivatives via the Hantzsch condensation is described. The present methodology offers several advantages such as simple procedure, excellent yields, and short reaction time.

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References

  1. A. Domling, I. Ugi, Angew. Chem Int. Ed. 39 (2000) 3168

    CAS  Google Scholar 

  2. L. Yu, B. Chen, X. Huang, Tetrahedron Lett. 48 (2007) 925.

    Google Scholar 

  3. M. Kawase, A. Shah, H. Gaveriya, N. Motohashi, H. Sakagami, A.V. Molnar, J. Bioorg. Med. Chem. 10 (2002) 1051

    CAS  Google Scholar 

  4. R. Mannhold, B. Jablonka, W. Voigdt, K. Schoenafinger, K. Schravan, Eur. J. Med. Chem. 27 (1992) 229.

    CAS  Google Scholar 

  5. S. Visentin, B. Rolando, D.A. Stilo, R. Fruttero, M. Novara, E. Carbone, C. Roussel, N. Vanthuyne, A. Gasco, J. Med. Chem. 475 (2004) 2688.

    Google Scholar 

  6. R. Toniolo, D.F. Narda, G. Bontempelli, F. Ursini, Bioelectro Chem. 51 (2000) 193.

    CAS  Google Scholar 

  7. H. Adibi, R.A. Hajipour, Bioorg. Med. Chem. Lett. 17 (2007) 1008.

    CAS  Google Scholar 

  8. B. Love, M.K. Sander, J. Org. Chem. 30 (1965) 1914.

    Google Scholar 

  9. S.J. Yadav, S.V.B. Reddy, K.A. Basak, V.A. Narasaiah, Green Chem. 5 (2003) 3

    Google Scholar 

  10. R. Sridhar, T.P. Perumal, Tetrahedron 61 (2005) 2465.

    CAS  Google Scholar 

  11. A. Agarwal, S.M.P. Chauhan, Tetrahedron Lett. 46 (2005) 1345

    CAS  Google Scholar 

  12. L. Ohberg, J. Westman, Synlett (2001) 126.

    Google Scholar 

  13. L.J. Donelson, A.R. Gibbs, K.S. De, J. Mol. Catal. A. 256 (2006) 309.

    CAS  Google Scholar 

  14. A.M. Chari, K. Syamasundar, Catal. Commun. 6 (2005) 624.

    Google Scholar 

  15. M.M. Heravi, K. Bakhtiari, M.N. Javadi, F.F. Bamoharram, M. Saeedi, A.H. Oskooie, J. Mol. Catal. A. 264 (2007) 50.

    CAS  Google Scholar 

  16. S. Ko, V.N.M. Sastry, C. Lin, F.C. Yao, Tetrahedron Lett. 46 (2005) 5771.

    CAS  Google Scholar 

  17. S. Ko, F.C. Yao, Tetrahedron 62 (2006) 7293.

    CAS  Google Scholar 

  18. M.L. Wang, J. Sheng, L. Zhang, W.J. Han, Y.Z. Fan, H. Tian, T.C. Qian, Tetrahedron 61 (2005) 1539.

    CAS  Google Scholar 

  19. A. Kumar, A.R. Maurya, Tetrahedron Lett. 48 (2007) 3887.

    CAS  Google Scholar 

  20. R. Singh, M.R. Kissling, A.M. Letellier, P.S. Nolan, J. Org. Chem. 69 (2004) 209

    CAS  Google Scholar 

  21. T.P. Anastas, B.L. Bartlett, M.M. Kirchhof, C.T. Williamson, Catal. Today 55 (2000) 11.

    CAS  Google Scholar 

  22. K. Tanabe, Solid Acids and Bases, Academic Press, New York, 1970.

    Google Scholar 

  23. F. Tamaddom, A.M. Amrollahi, L. Sharafat, Tetrahedron Lett. 46 (2005) 7841

    Google Scholar 

  24. M. Gupta, S. Paul, R. Gupta, A. Loupy, Tetrahedron Lett. 46 (2005) 4957

    CAS  Google Scholar 

  25. M. Hosseini-Sarvari, H. Sharghi, J. Org. Chem. 71 (2006) 6652

    CAS  Google Scholar 

  26. M. Hosseini-Sarvari, H. Sharghi, Tetrahedron 61 (2005) 10903

    CAS  Google Scholar 

  27. H. Sharghi, M. Hosseini-Sarvari, Synthesis 8 (2002) 1057

    Google Scholar 

  28. M. Hosseini-Sarvari, Synthesis 5 (2005) 787

    Google Scholar 

  29. M. Hosseini-Sarvari, H. Sharghi, Phos. Silicon. Sulf. 182 (2007) 2125

    CAS  Google Scholar 

  30. M. Hosseini-Sarvari, Synth. Commun. 16 (2008) 832

    Google Scholar 

  31. M. Hosseini-Sarvari, S. Etemad, Tetrahedron (2008) 5519

    Google Scholar 

  32. M. Hosseini-Sarvari, H. Sharghi, S. Etemad, Helv. Chim. Acta. 91 (2008) 715.

    CAS  Google Scholar 

  33. M.F. Moghaddam, H. Saeidian, Mater. Sci. Eng. B. 139 (2007) 265.

    CAS  Google Scholar 

  34. Z. Mirjafary, H. Saeidian, A. Sadeghi, M.F. Moghaddam, Catal. Commun. 9 (2008) 299.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Laboratory of Organic Synthesis and Natural products, Department of Chemistry, Sharif University of Technology, Tehran, Iran, P. O. Box 11155-9516, Tehran, Iran

    F. Matloubi Moghaddam, H. Saeidian, Z. Mirjafary & A. Sadeghi

Authors
  1. F. Matloubi Moghaddam
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  2. H. Saeidian
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  3. Z. Mirjafary
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  4. A. Sadeghi
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Correspondence to F. Matloubi Moghaddam.

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Moghaddam, F.M., Saeidian, H., Mirjafary, Z. et al. Rapid and efficient one-pot synthesis of 1,4-dihydropyridine and polyhydroquinoline derivatives through the Hantzsch four component condensation by zinc oxide. JICS 6, 317–324 (2009). https://doi.org/10.1007/BF03245840

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  • DOI: https://doi.org/10.1007/BF03245840

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