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Synthesis of 2-substituted 7-methylpyrimido[4,5-d]pyrimidin-4(3H)-ones catalyzed by heteropolyacids

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Abstract

A series of 2-substituted 7-methylpyrimido[4,5-d]pyrimidin-4(3H)-ones have been synthesized in good yields by reaction of 4-amino-2-methylpyrimidine-5-carboxamide with aromatic aldehydes in the presence of three heteropolyacids, H3PMo12O40, H3PW12O40, and H5PV2Mo10O40. In this reaction the catalytic activity of H3PMo12O40 and H3PW12O40 was lower than that of H5PV2Mo10O40. All the synthesized compounds were characterized on the basis of elemental analysis and spectral data (IR, 1H NMR, 13C NMR, and ESIMS). It is an effective way of synthesis of 2-substituted 7-methylpyrimido[4,5-d]pyrimidin-4(3H)-one derivatives, with the advantages of mild reaction conditions, simple operation, and good yields.

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References

  1. S.R. Roy, P.S. Jadhavar, K. Seth, K.K. Sharma, A.K. Chakraborti, Synthesis. 2261, 2269 (2011)

    Google Scholar 

  2. R. Gupta, A. Jain, R. Joshi, M. Jain, Bull. Korean Chem. Soc. 32, 899 (2011)

    Article  CAS  Google Scholar 

  3. M.G. Gebauer, C. Mckinlay, J.E. Gready, Eur. J. Med. Chem. 38, 719 (2003)

    Article  CAS  Google Scholar 

  4. M. Dabiri, H. Arvin-Nezhad, H.R. Khavasi, A. Bazgir, Tetrahedron 63, 1770 (2007)

    Article  CAS  Google Scholar 

  5. L.A. McDermott, B. Higgins, M. Simcox, K. Luk, T. Nevins, K. Kolinsky, M. Smith, H. Yang, J.K. Li, Y. Chen, Bioorg. Med. Chem. Lett. 16, 1950 (2006)

    Article  CAS  Google Scholar 

  6. S.M. El-Moghazy, D.A. Ibrahim, N.M. Abdelgawad, N.H. Farag, A.S. El-Khouly, Sci. Pharm. 79, 429 (2011)

    Article  CAS  Google Scholar 

  7. M.S. Mohamed, S.M. Awad, A.I. Sayed, Molecules 15, 1882 (2010)

    Article  CAS  Google Scholar 

  8. M.M. Youssef, M.A. Amin, Molecules 17, 9652 (2012)

    Article  CAS  Google Scholar 

  9. T. Wang, X.Y. Liu, J. Luo, X.M. Xu, D.H. Yu, Chin. J. Org. Chem. 31, 1773 (2011)

    CAS  Google Scholar 

  10. A.H. Kategaonkar, S.A. Sadaphal, K.F. Shelke, B.B. Shingate, M.S. Shingare, Ukr. Bioorg. Acta 1, 3 (2009)

    Google Scholar 

  11. M. Dabiri, H. Arvin-Nezhad, H.R. Khavasi, J. Heterocycl. Chem. 44, 1009 (2009)

    Google Scholar 

  12. M.G. Gebauer, C. McKinlay, J.E. Gready, Eur. J. Med. Chem. 38, 719 (2003)

    Article  CAS  Google Scholar 

  13. H. Kategaonkar, S.A. Sadaphal, K.F. Shelke, Ukr. Bioorg. Acta 7, 12 (2009)

    Google Scholar 

  14. M. Güllü, A. Dinçsönmez, Ö. Özyavaş, Eur. J. Org. Chem. 2010, 2113 (2010)

    Article  Google Scholar 

  15. Y. Aksinenko, V.B. Sokolov, T.V. Goreva, Rus. Chem. Bull. 57, 1543 (2008)

    Article  CAS  Google Scholar 

  16. M.R. Mohammadizadeh, M. Bahramzadeh, A.A. Mohammadi, Helv. Chim. Acta 93, 153 (2010)

    Article  CAS  Google Scholar 

  17. M. Arabi, M.M. Amini, M. Abedini, A. Nemati, M. Alizadeh, J. Mol. Catal. A 200, 105 (2003)

    Article  CAS  Google Scholar 

  18. M.M. Heravi, R. Motamedia, N. Seifi, F.F. Bamoharram, J. Mol. Catal. A 249, 105 (2006)

    Article  Google Scholar 

  19. Z.D. Fang, X.H. Wei, J. Chem. Res. 36, 703 (2012)

    Article  CAS  Google Scholar 

  20. Z.D. Fang, X.H. Wei, Heterocycles 85, 2757 (2012)

    Article  CAS  Google Scholar 

  21. H. Tao, Y.L. Kang, T. Taldone, G. Chiosis, Bioorg. Med. Chem. Lett. 19, 415 (2009)

    Article  CAS  Google Scholar 

  22. E.S. Darwish, M.A. Mosselhi, F.M. Altalbawy, H.A. Saad, Molecules 16, 8788 (2011)

    Article  CAS  Google Scholar 

  23. S. Sahnoun, S. Messaoudi, J. Peyrat, J.D. Brion, M. Alami, Tetrahedron. Lett. 49, 7279 (2008)

    Article  CAS  Google Scholar 

  24. M.M. Heravi, R. Motamedi, F.F. Bamoharram, N. Seify, Catal. Commun. 8, 1467 (2007)

    Article  CAS  Google Scholar 

  25. M.M. Heravi, V. Rasmi, F.F. Bamoharram, S. Sadjadi, L. Fotouhi, S. Sadjadi, B. Mehdi, Synth. Commun. 39, 4109 (2009)

    Article  CAS  Google Scholar 

  26. A. Davoodnia, M. Bakavoli, G. Barakouhi, N. Tavakoli-Hoseini, Chin. Chem. Lett. 18, 1483 (2007)

    Article  CAS  Google Scholar 

  27. M.M. Heravi, S. Sadjadi, J. Iran. Chem. Soc. 6, 1 (2009)

    Article  CAS  Google Scholar 

  28. R. Hekmatshoar, S. Sajadi, M.M. Heravi, F.F. Bamoharram, Molecules 12, 2223 (2007)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. College of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi, 435002, Hubei, People’s Republic of China

    Zheng Dong Fang & Yu Yuan Tan

  2. College of Art and Science of Hubei Normal University, Huangshi, 435002, People’s Republic of China

    Di Fang

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  1. Zheng Dong Fang
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  2. Di Fang
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  3. Yu Yuan Tan
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Correspondence to Zheng Dong Fang.

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Fang, Z.D., Fang, D. & Tan, Y.Y. Synthesis of 2-substituted 7-methylpyrimido[4,5-d]pyrimidin-4(3H)-ones catalyzed by heteropolyacids. Res Chem Intermed 41, 1203–1211 (2015). https://doi.org/10.1007/s11164-013-1266-1

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  • DOI: https://doi.org/10.1007/s11164-013-1266-1

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