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A viable and efficacious catalyst, CeO2/HAp, for green synthesis of novel pyrido[2,3-d]pyrimidine derivatives

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Abstract

A facile one-pot green protocol at room temperature has been devised for the synthesis of novel pyrido[2,3-d]-pyrimidine derivatives catalyzed by CeO2-doped hydroxyapatite (CeO2/HAp) with ethanol as solvent. This highly selective method with excellent yields (89–96%) involves a four-component reaction between malononitrile, substituted aldehyde, dimethylbarbituric acid and ammonium acetate. CeO2/HAp was synthesized and characterized by P-XRD, TGA, TEM and SEM analyses. The structures of the target molecules were confirmed by diverse spectroscopic methods (1H NMR, 15N NMR, 13C NMR, and HRMS). Additional benefits of this eco-friendly approach are the operational simplicity, a stable catalyst with good reusability (at least 6 times), short reaction times (< 45 min) and no need for chromatographic separations. All these features make the proposed method economical and sustainable.

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References

  1. K. Alfonsi, J. Colberg, P.J. Dunn, T. Fevig, S. Jennings, T.A. Johnson, P. Kleine, C. Knight, M.A. Nagy, D.A. Perry, M. Stefaniak, Green Chem. 10, 31 (2008)

    Article  CAS  Google Scholar 

  2. S. Shabalala, S. Maddila, W.E. Van Zyl, S.B. Jonnalagadda, Catal. Commun. 79, 21 (2016)

    Article  CAS  Google Scholar 

  3. S. Maddila, S. Rana, R. Pagadala, S. Kankala, S.N. Maddila, S.B. Jonnalagadda, Catal. Commun. 61, 26 (2015)

    Article  CAS  Google Scholar 

  4. M.B. Gawande, V.D.B. Bonifacio, R. Luque, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42, 5522 (2013)

    Article  CAS  Google Scholar 

  5. A. Domling, W. Wang, K. Wang, Chem. Rev. 112, 3083 (2012)

    Article  CAS  Google Scholar 

  6. I.T. Horvath, P.T. Anastas, Chem. Rev. 107, 2169 (2007)

    Article  CAS  Google Scholar 

  7. S.N. Maddila, S. Maddila, W.E. Van Zyl, S.B. Jonnalagadda, ChemistryOpen 5, 38 (2016)

    Article  CAS  Google Scholar 

  8. S. Maddila, S. Rana, R. Pagadala, S.B. Jonnalagadda, Res. Chem. Intermed. 41, 8269 (2015)

    Article  CAS  Google Scholar 

  9. P.J. Walsh, H. Li, C.A.D. Parrodi, Chem. Rev. 107, 2503 (2007)

    Article  CAS  Google Scholar 

  10. K.H. Zuo, Y.-P. Zeng, D. Jiang, Mater. Sci. Eng. C 30, 283 (2010)

    Article  CAS  Google Scholar 

  11. K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 122, 7144 (2000)

    Article  CAS  Google Scholar 

  12. T. Tsuchida, J. Kubo, T. Yoshioka, S. Sakuma, T. Takeguchi, W. Ueda, J. Catal. 259, 183 (2008)

    Article  CAS  Google Scholar 

  13. S. Sebti, R. Tahir, R. Nazih, S. Boulaajaj, Appl. Catal. A Gen. 218, 25 (2001)

    Article  CAS  Google Scholar 

  14. B.M. Choudary, C. Sridhar, M.L. Kantam, B. Sreedhar, Tetrahedron Lett. 45, 7319 (2004)

    Article  CAS  Google Scholar 

  15. M. Spencer, M. Grynpas, J. Chromat. A. 166, 423 (1978)

    Article  CAS  Google Scholar 

  16. Y. Liu, H. Tsunoyama, T. Akita, T. Tsukuda, Chem. Commun. 46, 550 (2010)

    Article  CAS  Google Scholar 

  17. R. Stürmer, Angew. Chem. Int. Ed. 38, 3307 (1999)

    Article  Google Scholar 

  18. S.R. Kale, S.S. Kahandal, M.B. Gawande, R.V. Jayaram, RSC Adv. 3, 8184 (2013)

    Article  CAS  Google Scholar 

  19. K. Wang, G.J. Kennedy, R.A. Cook, J. Mol. Catal. A Chem. 298, 88 (2009)

    Article  CAS  Google Scholar 

  20. S. Koutsopoulos, J. Biomed. Mater. Res. 62, 600 (2002)

    Article  CAS  Google Scholar 

  21. M. Melchionna, P. Fornasiero, Mater. Today 17, 349 (2014)

    Article  CAS  Google Scholar 

  22. T.A. Farghaly, H.M. Hassaneen, Arch. Pharm. Res. 36, 564 (2013)

    Article  CAS  Google Scholar 

  23. F. Herold, J. Kleps, A. Chodkowski, B. Gutkowska, Acta Pol. Pharm. 56, 385 (1999)

    CAS  Google Scholar 

  24. A. Banerjee, M.Y. Pawar, S. Patil, P.S. Yadav, P.A. Kadam, V.G. Kattige, D.S. Deshpande, P.V. Pednekar, M.K. Pisat, L.A. Gharat, Bioorg. Med. Chem. Lett. 24, 4838 (2014)

    Article  CAS  Google Scholar 

  25. C. Kurumurthy, S.P. Rao, V.B. Swamy, S.G. Kumar, S.P. Rao, B. Narsaiah, L.R. Velatooru, R. Pamanji, V.J. Rao, Eur. J. Med. Chem. 46, 3462 (2011)

    Article  CAS  Google Scholar 

  26. M.N. Nasr, M.M. Gineinah, Arch. Pharm. (Weinheim) 335, 289 (2002)

    Article  CAS  Google Scholar 

  27. S.P. Satasia, P.N. Kalaria, D.K. Raval, Org. Biomol. Chem. 12, 1751 (2014)

    Article  CAS  Google Scholar 

  28. S. Maddila, S.K. Avula, S. Gorle, M. Singh, L. Palakondu, S.B. Jonnalagadda, Lett. Drug Des. Discov. 10, 186 (2013)

    Article  CAS  Google Scholar 

  29. D.A. Ibrahim, N.S. Ismail, Eur. J. Med. Chem. 46, 5825 (2011)

    Article  CAS  Google Scholar 

  30. Q. Ren, Z. Cui, H. He, Y. Gu, J. Fluor. Chem. 128, 1369 (2007)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  32. S.E.A. Abdel-Aziz, Synth. Commun. 30, 2223 (2000)

    Article  Google Scholar 

  33. S. Maddila, M. Momin, L. Palakondu, C.V. Rao, J. Saudi Chem. Soc. 20, 173 (2016)

    Article  CAS  Google Scholar 

  34. S. Maddila, S.N. Maddila, S.B. Jonnalagadda, L. Palakondu, J. Heterocycl. Chem. 53, 658 (2016)

    Article  CAS  Google Scholar 

  35. S. Maddila, J. Valand, H. Bandaru, Y. Kotaiah, L. Palakondu, J. Heterocycl. Chem. 53, 319 (2016)

    Article  CAS  Google Scholar 

  36. S. Maddila, K. Naicker, M. Momin, S. Rana, S. Gorle, S.N. Maddila, Y. Kotaiah, M. Singh, S.B. Jonnalagadda, Med. Chem. Res. 25, 283 (2016)

    Article  CAS  Google Scholar 

  37. S. Maddila, M. Momin, S. Gorle, L. Palakondu, S.B. Jonnalagadda, J. Chile. Chem. Soc. 60, 2774 (2015)

    Article  Google Scholar 

  38. S. Maddila, R. Pagadala, S.B. Jonnalagadda, Lett. Org. Chem. 10, 693 (2013)

    Article  CAS  Google Scholar 

  39. S. Maddila, S. Gorle, M. Singh, L. Palakondu, S.B. Jonnalagadda, Lett. Drug Des. Discov. 10, 977 (2013)

    Article  CAS  Google Scholar 

  40. S. Maddila, R. Pagadala, S.B. Jonnalagadda, J. Heterocycl. Chem. 52, 487 (2015)

    Article  CAS  Google Scholar 

  41. M.K. Pillai, S. Singh, S.B. Jonnalagadda, Synth. Commun. 40, 3710 (2010)

    Article  CAS  Google Scholar 

  42. M.K. Pillai, S. Singh, S.B. Jonnalagadda, Kinet. Catal. 52, 536 (2011)

    Article  CAS  Google Scholar 

  43. R. Pagadala, S. Maddila, S. Rana, B. Moodley, N.A. Koorbanally, S.B. Jonnalagadda, RSC Adv. 5, 5627 (2015)

    Article  CAS  Google Scholar 

  44. R. Pagadala, S. Maddila, S. Rana, S.B. Jonnalagadda, RSC Adv. 4, 6602 (2014)

    Article  CAS  Google Scholar 

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Acknowledgement

The authors are grateful to the National Research Foundation (NRF) of South Africa, and the University of KwaZulu-Natal, Durban, for financial support and research facilities.

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Authors and Affiliations

  1. School of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Chiltern Hills, Durban, 4000, South Africa

    Suresh Maddila, Kranthi Kumar Gangu, Surya Narayana Maddila & Sreekantha B. Jonnalagadda

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  1. Suresh Maddila
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  2. Kranthi Kumar Gangu
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  3. Surya Narayana Maddila
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  4. Sreekantha B. Jonnalagadda
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Correspondence to Sreekantha B. Jonnalagadda.

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Maddila, S., Gangu, K.K., Maddila, S.N. et al. A viable and efficacious catalyst, CeO2/HAp, for green synthesis of novel pyrido[2,3-d]pyrimidine derivatives. Res Chem Intermed 44, 1397–1409 (2018). https://doi.org/10.1007/s11164-017-3174-2

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