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Rapid three-component synthesis of pyrimidine and pyrimidinone derivatives in the presence of Bi(NO3)3·5H2O as a mild and highly efficient catalyst

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Abstract

Bismuth(III) nitrate pentahydrate is found as a mild and highly efficient catalyst for the rapid synthesis of 4-amino-5-pyrimidine carbonitrile and pyrimidinone derivatives via three-component reaction of aldehydes, N-unsubstituted amidines, and malononitrile or ethyl cyanoacetate under thermal aqueous conditions. The reaction protocol is rapid and simple which is followed by formation of the corresponding pyrimidine and pyrimidinone derivatives in good to excellent yields with high purity.

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References

  1. S.F. Wnuk, E. Lewandowska, D.R. Companioni, P.I. García Jr., J.A. Secrist III, Org. Biomol. Chem 2, 120 (2004)

    Article  CAS  Google Scholar 

  2. N.A. Hassan, Molecules 5, 826 (2000)

    Article  CAS  Google Scholar 

  3. M. Pemmsin, C. Lnu-Due, F. Hoguet, C. Gaultier, J. Narciss, Eur. J. Chem. 23, 543 (1988)

    Google Scholar 

  4. A. Cannito, M. Pemmsin, C. Lnu-Due, F. Hoguet, C. Gaultier, J. Narcisse, Eur. J. Chem. 25, 635 (1990)

    Article  CAS  Google Scholar 

  5. P.A.S. Smith, R.O. Kan, J. Org. Chem. 29, 2261 (1964)

    Article  CAS  Google Scholar 

  6. S. Nega, J. Aionso, A. Diazj, F. Junquere, J. Heterocycl. Chem. 27, 269 (1990)

    Article  Google Scholar 

  7. C.J. Shishoo, K.S. Jain, J. Heterocycl. Chem. 29, 883 (1992)

    Article  CAS  Google Scholar 

  8. J.U.S. Peters, D. Hunziker, H. Fischer, M. Kansy, S. Weber, S. Kritter, A. Muller, F. Ricklin, M. Boehringer, S.M. Poli, M. Csato, B.M. Loeffler, Bioorg. Med. Chem. Lett. 14, 3575 (2004)

    Article  CAS  Google Scholar 

  9. H. Hattori, Heterogeneous basic catalysis. Chem. Rev. 95, 537 (1995)

    Article  CAS  Google Scholar 

  10. B.K. Banik, A.T. Reddy, A. Datta, C. Mukhopadhyay, Tetrahedron Lett. 48, 7392 (2007)

    Article  CAS  Google Scholar 

  11. I. Mohammadpoor-Baltork, M.M. Khodaei, K. Nikoofar, Tetrahedron Lett. 44, 591 (2003)

    Article  CAS  Google Scholar 

  12. S. Samajdar, F.F. Becker, B.K. Banik, Tetrahedron Lett. 41, 8017 (2000)

    Article  CAS  Google Scholar 

  13. B.K. Banik, N. Srivastava, S.K. Dasgupta, Tetrahedron Lett. 44, 1191 (2003)

    Article  Google Scholar 

  14. B.K. Banik, N. Srivastava, J. Org. Chem. 68, 2109 (2003)

    Article  Google Scholar 

  15. S.D. Samant, V.M. Alexander, R.P. Bhat, Tertrahedron Lett. 46, 6957 (2005)

    Article  Google Scholar 

  16. S. Cunha, M.T. Rodrigues, Tertrahedron Lett. 47, 6955 (2006)

    Article  CAS  Google Scholar 

  17. H. Sheibani, A. Saljoogi, A.S. Bazgir, Arkivoc. 2, 115 (2008)

    Article  Google Scholar 

  18. H. Sheibani, M. Seifi, A. Bazgir, Synth. Commun. 39, 1055 (2009)

    Article  CAS  Google Scholar 

  19. H. Sheibani, F. Hassani, J. Heterocycl. Chem. 48, 915 (2011)

    Article  CAS  Google Scholar 

  20. M. Seifi, H. Sheibani, Catal. Lett. 126, 275 (2008)

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The authors express appreciation to the Shahid Bahonar University of Kerman Faculty Research Committee Fund for its support of this investigation.

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Correspondence to Hassan Sheibani.

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Zahedifar, M., Sheibani, H. Rapid three-component synthesis of pyrimidine and pyrimidinone derivatives in the presence of Bi(NO3)3·5H2O as a mild and highly efficient catalyst. Res Chem Intermed 41, 105–111 (2015). https://doi.org/10.1007/s11164-013-1172-6

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  • DOI: https://doi.org/10.1007/s11164-013-1172-6

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