Skip to main content
Log in

Catalyst-free synthesis of dihydropyridine from barbituric acid in water

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

Abstract

An operationally simple, atom-economical, and green procedure has been developed for the synthesis of dihydropyridine derivatives by a simple condensation of barbituric acid, aldehyde, and ammonium acetate in water under catalyst-free conditions. Excellent yields and purity were obtained with only filtration and washing with hot water and ethanol.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1

Similar content being viewed by others

References

  1. J.R. Quinn, S.C. Zimmerman, Org. Lett. 6, 1649 (2004)

    Article  CAS  Google Scholar 

  2. S. Djurdjevic, D.A. Leigh, H. McNab, S. Parsons, G. Teobaldi, F. Zerbetto, J. Am. Chem. Soc. 129, 476 (2007)

    Article  CAS  Google Scholar 

  3. J. Taubitz, U. Lüning, Eur. J. Org. Chem. 35, 5922–5927 (2008)

    Google Scholar 

  4. Z.S. Derewenda, U. Derewenda, P.M. Kobos, J. Mol. Biol. 241, 83–93 (1994)

    Article  CAS  Google Scholar 

  5. J. Bellaf, H.M. Bermanf, J. Mol. Biol. 264, 734–742 (1996)

    Article  Google Scholar 

  6. P. Chakrabarti, S. Chakrabarti, J. Mol. Biol. 284, 867–873 (1998)

    Article  CAS  Google Scholar 

  7. Z. Berkovitch-Yellin, L. Leiserowitz, Acta. Cryst. B 40, 159–165 (1984)

    Article  Google Scholar 

  8. L.J.W. Shimon, M. Vaida, L. Addadi, M. Lahav, L. Leiserowitz, J. Am. Chem. Soc. 112, 6215–6220 (1990)

    Article  CAS  Google Scholar 

  9. G.R. Desiraju, Angew. Chem. Int. Ed. 34, 2311–2327 (1995)

    Article  CAS  Google Scholar 

  10. K.N. Houk, S. Menzer, S.P. Newton, R.M. Raymo, J.F. Stoddart, D.J. Williams, J. Am. Chem. Soc. 121, 1479–1487 (1999)

    Article  CAS  Google Scholar 

  11. R.A. Musah, G.M. Jensen, R.J. Rosenfeld, D.E. McRee, D.B. Goodin, J. Am. Chem. Soc. 119, 9083–9084 (1997)

    Article  CAS  Google Scholar 

  12. G. Cooke, V.M. Rotello, Chem. Soc. Rev. 31, 275–286 (2002)

    Article  CAS  Google Scholar 

  13. M. Kidwai, S. Saxena, M.K. Rahman Khan, S.S. Thukral, Bioorg. Med. Chem. Lett. 15, 4295–4298 (2005)

    Article  CAS  Google Scholar 

  14. M. Kidwai, K. Singhal, J. Heterocycl Chem. 44, 1253–1257 (2011)

    Google Scholar 

  15. S.V. Chankeshwara, A.K. Chakraborti, Org. Lett. 8, 3259–3262 (2006)

    Article  CAS  Google Scholar 

  16. G.L. Khatik, R. Kumar, A.K. Chakraborti, Org. Lett. 8, 2433–2436 (2006)

    Article  CAS  Google Scholar 

  17. N. Azizi, M.R. Saidi, Org. Lett. 7, 3649–3651 (2005)

    Article  CAS  Google Scholar 

  18. N. Azizi, F. Aryanasab, L. Torkiyan, A. Ziyaei, M.R. Saidi, J. Org. Chem. 71, 3634–3635 (2006)

    Article  CAS  Google Scholar 

  19. N. Azizi, L. Torkiyan, M.R. Saidi, Org. Lett. 8, 2079–2082 (2006)

    Article  CAS  Google Scholar 

  20. N. Azizi, F. Aryanasab, M.R. Saidi, Org. Lett. 8, 5275–5278 (2006)

    Article  CAS  Google Scholar 

  21. A.R. Khajeh Amiri, N. Azizi, M. Bolourtchian, M.R. Saidi, Synlett 14, 2245–2248 (2009)

    Google Scholar 

  22. A.R. Khajeh Amiri, N. Azizi, M. Bolourtchian, Mol. Divers. 15(1), 157–161 (2011)

    Article  Google Scholar 

  23. M.M. Sanchez Duque, C. Allais, N. Isambert, T. Constantieux, J. Rodriguez, Top. Heterocycl. Chem. 23, 227–277 (2010)

    Article  Google Scholar 

  24. G. Bartoli, M. Bosco, P. Galzerano, R. Giri, A. Mazzanti, P. Melchiorre, L. Sambri, Eur. J. Org. Chem. 2008(23), 3970–3975 (2008)

    Article  Google Scholar 

  25. M. Kidwaia, K. Singhala, Synth. Commun. 36, 1887–1891 (2006)

    Article  Google Scholar 

  26. R.A. Mekheimer, A.A. Hameed, K. Sadek, Green Chem. 10, 592–593 (2008)

    Article  CAS  Google Scholar 

  27. J.S. Yadav, B.V.S. Reddy, A.K. Basak, A.V. Narsaiah, Green Chem. 5, 60–63 (2003)

    Article  CAS  Google Scholar 

  28. M. Kidwai, K. Singhal, Can. J. Chem. 85, 400–405 (2007)

    Article  CAS  Google Scholar 

  29. K. Singh, J. Singh, H. Singh, Tetrahedron 54, 935–942 (1998)

    Article  CAS  Google Scholar 

  30. S.D. Sharma, P. Hazarika, D. Konwar, Catal. Commun. 9, 709–714 (2008)

    Article  Google Scholar 

  31. S. Koa, C.F. Yao, Tetrahedron 62, 7293–7299 (2006)

    Article  Google Scholar 

  32. P. Gupta, S. Gupta, R.L. Sharma, Indian J. Chem. Sect. B Org. Chem. Incl. Med. Chem. 48, 1187–1194 (2009)

    Google Scholar 

Download references

Acknowledgments

The financial support of this work provided by Chemistry and Chemical Research Center of Iran and Iran National Science Foundation (INSF) is gratefully appreciated.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Najmadin Azizi or Alireza Khajeh Amiri.

Electronic supplementary material

Experimental details and spectroscopic characterization (copy of 1H and 13C NMR and mass) of all compounds.

Supplementary material 1 (DOC 11157 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Azizi, N., Mobinikhaledi, A., Amiri, A.K. et al. Catalyst-free synthesis of dihydropyridine from barbituric acid in water. Res Chem Intermed 38, 2271–2275 (2012). https://doi.org/10.1007/s11164-012-0543-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0543-8

Keywords

Navigation