Skip to main content
SpringerLink
Log in

Ultrasound-mediated, uranyl nitrate hexahydrate-catalyzed synthesis of 1,4-dihydropyridines under mild conditions

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Synthesis of 1,4-dihydropyridines by three-component condensation reaction of aldehyde, 1,3-dicarbonyl compounds, and ammonium acetate have been found to be efficiently catalyzed by uranyl nitrate hexahydrate [UO2(NO3)2 ·6H2O] at room temperature under ultrasound irradiation. This novel synthetic method offers the advantages of high yields, short reaction times, simplicity, and easy workup compared to the conventional methods reported in the literature.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. A.C. Gaudio, A. Korolkovas, Y. Takahata, J. Pharm. Sci. 83, 1110 (1994)

    Article  CAS  Google Scholar 

  2. K.J. Schleifer, J. Med. Chem. 42, 2204 (1999)

    Article  CAS  Google Scholar 

  3. T. Godfraid, R. Miller, M. Wibo, Pharmocol. Rev. 38, 321 (1986)

    Google Scholar 

  4. B. Khadilkar, S. Borkar, Synth. Commun. 28, 207 (1998)

    Article  CAS  Google Scholar 

  5. B. Schnell, W. Krenn, K. Faber, C.O. Kappe, J. Chem. Soc. Perkin Trans. 1, 4382 (2000)

    Article  Google Scholar 

  6. G. Sabitha, G.S. Reddy, C.S. Reddy, Tetrahedron Lett. 44, 4129 (2003)

    Article  CAS  Google Scholar 

  7. D.M. Stout, A.I. Meyers, Chem. Rev. 82, 223 (1982)

    Article  CAS  Google Scholar 

  8. S.J. Ji, Z.Q. Jiang, J. Lu, T.P. Loh, Synlett 5, 831 (2004)

    Article  Google Scholar 

  9. M. Suárez, E. Ochoa, Y. Verdecia, Tetrahedron 55, 875 (1999)

    Article  Google Scholar 

  10. S. Tu, Q. Wei, H. Ma, Synth. Commun. 31, 2657 (2001)

    Article  CAS  Google Scholar 

  11. S.R. Pattan, V.B. Rasal, N. Venkatramana, A.B. Khade, S.R. Butle, S.G. Jadhav, B.G. Desai, F.V. Manvi, Indian J. Chem. 46B, 698 (2007)

    CAS  Google Scholar 

  12. T. Suresh, S.K. Swamy, V.M. Reddy, Indian J. Chem. 46B, 115 (2007)

    CAS  Google Scholar 

  13. M.A. Ali, D.A. Chowdhary, M. Naziruddin, Polyhedron 3, 595 (1984)

    Article  CAS  Google Scholar 

  14. J.P. Scovill, D.L. Klayman, C.F. Franchino, J. Med. Chem. 25, 1261 (1982)

    Article  CAS  Google Scholar 

  15. B. Palakshi Reddy, K. Rajesh, V. Vijayakumar, J. Chin. Chem. Soc. 58, 384 (2011)

    Article  Google Scholar 

  16. R.S. Rathore, B.P. Reddy, V. Vijayakumar, R.V. Ragavan, T. Narasimhamurthy, Acta Cryst. B65, 375 (2009)

    Article  Google Scholar 

  17. B. Palakshi Reddy, K. Rajesh, V. Vijayakumar, Arab. J. Chem. (2011), doi:10.1016/j.arabjc.2011.01.027

  18. B. Palakshi Reddy, K. Rajesh, V. Vijayakumar, Ind. J. Heterocyclic Chem. 20, 281 (2011)

  19. K. Rajesh, B. Palakshi Reddy, V. Vijayakumar, Can. J. Chem. 89, 1236 (2011)

    Article  CAS  Google Scholar 

  20. B. Palakshi Reddy, K. Rajesh and V. Vijayakumar, Org. Prep. Proced. Int. 44, 153 (2012)

  21. K. Rajesh, P. Iniyavan, S. Sarveswari and V. Vijayakumar, Res. Chem. Intermed. doi 10.1007/s11164-013-1085-4

  22. G.L. Balaji, K. Rajesh, M. Venkatesh, S. Sarveswari, V. Vijayakumar, RSC Advances 4, 39–46 (2014)

    Article  CAS  Google Scholar 

  23. M.A. Hayat, Principles and techniques of electron microscopy (Van Nostrand Reinhold, New York, 1970)

    Google Scholar 

  24. J.J.V. Eynde, F. Delfosse, A. Mayence, Y.V. Haverbeke, Tetrahedron 51, 6511 (1995)

    Article  Google Scholar 

  25. F. Tamaddon, Z. Razmi, A.A. Jafari, Tetrahedron Lett. 51, 1187 (2010)

    Article  CAS  Google Scholar 

  26. A. Debache, W. Ghalem, R. Boulcina, A. Belfaitah, S. Rhouati, B. Carboni, Tetrahedron Lett. 50, 5248 (2009)

    Article  CAS  Google Scholar 

  27. A. Shaabani, A.H. Rezayan, A. Rahmati, Monatsh. Chem. 137, 77 (2006)

    Article  CAS  Google Scholar 

  28. K. Tetsuji, O. Kunio, Yakugaku Zasshi 86, 815 (1966)

    Google Scholar 

  29. L. E. Hinkel, A. E. Ernest, W. H. Morgan, J. Chem. Soc. 1835 (1931)

  30. B.M. Khadilkar, V.G. Gaikar, A.A. Chitnavis, Tetrahedron Lett. 36, 8083 (1995)

    Article  CAS  Google Scholar 

  31. M. Maheswara, V. Siddaiah, Y.K. Rao, Y.M. Tzeng, C. Sridhar, J. Mol. Catal. A: Chem. 260, 179 (2006)

    Article  CAS  Google Scholar 

  32. D. Kumar, S. Anil Suresh, S.J. Sandhu, J. Indian Chem. Soc. 86, 996 (2009)

    CAS  Google Scholar 

  33. M.V. Lembkge, A. Nuhrichl, V. Zemb, G. Devaux, P. Vacherl, A.M. Vacher, B. Dufy, Eur. J. Med. Chem. 31, 547 (1996)

    Article  Google Scholar 

  34. H.R. Memarian, M. Bagheri, D. Dietrich, Monatsh. Chem. 135, 833 (2004)

    Article  CAS  Google Scholar 

  35. D.B. Shinde, N.D. Shinde, M.S. Shingare, M.P. Dubey, G.K. Patnaik, Indian J. Chem. 34B, 920 (1995)

    CAS  Google Scholar 

  36. H.R. Memarian, M.M. Sadeghi, A.R. Momeni, D. Dietrich, Monatsh. Chem. 133, 661 (2002)

    Article  CAS  Google Scholar 

  37. N.N. Pawel, B. Roman, Acta Pol. Pharm. 31, 279 (1974)

    Google Scholar 

  38. C. Safak, I. Sahin, R. Sunal, Arzneimittelforschung 40, 119 (1990)

    CAS  Google Scholar 

  39. B. Palakshi Reddy, V. Vijayakumar, S. Sarveswari, T. Narasimhamurthy, E.R.T. Tiekink, Acta Cryst. E66, o658 (2010)

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Centre for Organic and Medicinal Chemistry, VIT University, Vellore, 632 014, Tamil Nadu, India

    B. Palakshi Reddy, S. Sarveswari & V. Vijayakumar

Authors
  1. B. Palakshi Reddy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Sarveswari
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. Vijayakumar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. Vijayakumar.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Palakshi Reddy, B., Sarveswari, S. & Vijayakumar, V. Ultrasound-mediated, uranyl nitrate hexahydrate-catalyzed synthesis of 1,4-dihydropyridines under mild conditions. Res Chem Intermed 41, 6877–6883 (2015). https://doi.org/10.1007/s11164-014-1784-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-014-1784-5

Keywords

Search

Navigation