Skip to main content
Log in

Green approach to synthesis of new series of 6,8a-dihydropyrido[2,3-d]pyrimidine derivatives

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

One-pot, three-component condensation reaction between (phenylsulfonyl)acetonitrile, aromatic aldehydes, and 6-aminouracil for preparation of 6,8a-dihydropyrido[2,3-d]pyrimidine derivatives has been reported. The method involves domino Knoevenagel condensation/Michael addition, and cyclization cascade. The reaction was performed in glycerol which is commercially available, inexpensive and non-toxic compound. High purity of the products, very high yields and wide scope of substrates are advantages of this protocol.

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.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1

Similar content being viewed by others

References

  1. M.C. Bagley, D.D. Hughs, R. Lioyd, V.E.C. Powers, Tetrahedron Lett. 42, 6585–6588 (2001)

    Article  CAS  Google Scholar 

  2. F. Buron, J.Y. Merour, M. Akssira, G. Guillaumet, S. Routier, Eur. J. Med. Chem. 95, 46–95 (2015)

    Article  CAS  Google Scholar 

  3. M. Mamaghani, R. Hossein Nia, J. Heterocyclic. Chem. 54, 1700–1722 (2017)

    Article  CAS  Google Scholar 

  4. M. Shiri, Chem. Rev. 112, 3508–3549 (2012)

    Article  CAS  PubMed  Google Scholar 

  5. S. Asghari, S. Ramezania, M. Mohsenib, Chin. Chem. Lett. 25, 431–434 (2014)

    Article  CAS  Google Scholar 

  6. D.J. Berry, Ch.V. Digiovanna, S.S. Metrick, R. Murugan, Arkivoc., 201–226 (2001)

  7. M.F. Brana, M. Cacho, M.L. Garcia, E.P. Mayoral, B. Lopez, B. Teresa, J. Med. Chem. 48, 6843–6854 (2005)

    Article  CAS  PubMed  Google Scholar 

  8. M.L. Deb, P.J. Bhuyan, Synth. Commun. 36, 3085–3090 (2006)

    Article  CAS  Google Scholar 

  9. A.B. Deyanov, R.K. Niyazov, F.Y. Nazmetdivov, B.Y. Syropyatov, V.E. Kolla, M.E. Konshin, J. Pharm. Chem. 25, 248–250 (1991)

    Article  Google Scholar 

  10. I.O. Donkor, C.L. Klein, L. Liang, N. Zhu, E. Bradley, A.M. Clark, J. Pharm. Sci. 84, 661–664 (1995)

    Article  CAS  PubMed  Google Scholar 

  11. E.K. Goharshadi, Y. Ding, N.M. Jorabachi, P. Nancarrow, Ultrason. Sonochem. 16, 120–123 (2009)

    Article  CAS  PubMed  Google Scholar 

  12. S. Heck, A. Domling, Synlett. 3, 424–426 (2000)

    Google Scholar 

  13. P.T. Anastas, J.C. Warner, Green chemistry: theory and practice (Oxford University Press, Oxford, 1998)

    Google Scholar 

  14. M. Lancaster, Green Chemistry: an introductory text, 2nd edn. (RSC Publishing, Cambridge, 2010)

    Google Scholar 

  15. W.M. Nelson, Green solvents for chemistry: perspectives and practice (Oxford University Press, New York, 2003)

    Google Scholar 

  16. J.H. Clark, S.J. Taverner, Org. Process Res. Dev. 11, 149–155 (2007)

    Article  CAS  Google Scholar 

  17. F.M. Kerton, Alternative solvents for green chemistry (RSC Publishing, Cambridge, 2009)

    Google Scholar 

  18. P.G. Jessop, Green Chem. 13, 1391–1398 (2011)

    Article  CAS  Google Scholar 

  19. G. De Martino, M.C. Edler, G. La Regina, A. Coluccia, M.C. Barbera, D. Barrow, R.I. Nicholson, G. Chiosis, A. Brancale, E. Hamel, M. Artico, R. Silvestri, J. Med. Chem. 49, 947–954 (2006)

    Article  CAS  PubMed  Google Scholar 

  20. D.T. Johnson, K.A. Taconi, Environ. Prog. 26, 338–348 (2007)

    Article  CAS  Google Scholar 

  21. N. Bakhrou, F. Lamaty, J. Martinez, E. Colacino, Tetrahedron Lett. 51, 3935–3937 (2010)

    Article  CAS  Google Scholar 

  22. M. Li, C. Chen, F. He, Y. Gu, Adv. Synth. Catal. 352, 519–530 (2010)

    Article  CAS  Google Scholar 

  23. J. Francos, V. Cadierno, Green Chem. 12, 1552–1555 (2010)

    Article  CAS  Google Scholar 

  24. V.G. Ricordi, C.S. Freitas, G. Perin, E.J. Lenardão, R.G. Jacob, L. Savegnago, D. Alves, Green Chem. 14, 1030–1034 (2012)

    Article  CAS  Google Scholar 

  25. G. Perin, L.G. Mello, C.S. Radatz, L. Savegnago, D. Alves, R.G. Jacob, E.J. Lenardão, Tetrahedron Lett. 51, 4354–4356 (2010)

    Article  CAS  Google Scholar 

  26. C.S. Radatz, R.B. Silva, G. Perin, E.J. Lenardão, R.J. Jacob, D. Alves, Tetrahedron Lett. 52, 4132–4136 (2011)

    Article  CAS  Google Scholar 

  27. Y. Dommaraju, Sh Bora, D. Prajapati, Org. Biomol. Chem. 13, 9181–9185 (2015)

    Article  CAS  PubMed  Google Scholar 

  28. S. Singh, M. Saquib, M. Singh, J. Tiwari, F. Tufail, J. Singh, J. Singh, New. J. Chem. 40, 63–67 (2016)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We gratefully appreciate the University of Sistan and Baluchestan Research Councils for the financial support of this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hamid Reza Shaterian.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 2910 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Morshedi, A., Shaterian, H.R. Green approach to synthesis of new series of 6,8a-dihydropyrido[2,3-d]pyrimidine derivatives. J IRAN CHEM SOC 16, 493–500 (2019). https://doi.org/10.1007/s13738-018-1528-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-018-1528-3

Keywords

Navigation