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Preparation of pyrimidine derivatives through three-component reactions of dialkyl (2-oxo-3,3,3-trifluoropropyl)phosphonates

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Chemistry of Heterocyclic Compounds Aims and scope

Methods are proposed for the preparation of fluorophosphorus-containing pyrimidines through three- component reactions of dialkyl (3,3,3-trifluoro-2-oxopropyl)phosphonates. Cyclocondensation of these phosphonates with urea and aryl aldehydes gave 6-aryl-4-hydroxy-2-oxo-4-trifluoromethylhexa-hydropyrimidin-5-ylphosphonates and reaction with urea and trialkyl orthoformates led to 4-alkoxy-2-oxo-4-trifluoromethyl-1,2,3,4-tetrahydropyrimidin-5-ylphosphonates.

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References

  1. J. Zhu and H. Bienayme (editors), Multicomponent Reactions, Wiley-VCH, Weinheim (2005).

    Google Scholar 

  2. C. Simon, T. Constantieux, and J. Rodriguez, Eur. J. Org. Chem., 4957 (2004).

  3. S. V. Vdovina and V. A. Mamedov, Usp. Khim., 77, 1091 (2008).

    Google Scholar 

  4. D. Nagarathnam, S. W. Miao, B. Lagu, G. Chiu, J. Fang, T. G. Murali Dhar, J. Zhang, S. Tyagarajan, M. R. Marzabadi, F. Zhang, W. C. Wong, W. Sun, D. Tian, J. M. Wetzel, C. Forray, R. S. L. Chang, T. P. Broten, R. W. Ransom, T. W. Schorn, T. B. Chen, S. O'Malley, P. Kling, K. Schneck, R. Bendesky, C. M. Harrell, K. P. Vyas, and C. Gluchowski, J. Med. Chem., 42, 4764 (1999).

    Article  CAS  Google Scholar 

  5. K. S. Atwal, B. N. Swanson, S. E. Unger, D. M. Floyd, S. Moreland, A. Hedberg, and B. C. O'Reilly, J. Med. Chem., 34, 806 (1991).

    Article  CAS  Google Scholar 

  6. J.-P. Wan and Y. Liu, Synthesis, 3943 (2010).

  7. C. O. Kappe, Eur. J. Med. Chem., 35, 1043 (2000).

    Article  CAS  Google Scholar 

  8. K. Singh, D. Arora, and S. Singh, Mini-Rev. Med. Chem., 9, 95 (2009).

    Article  CAS  Google Scholar 

  9. D. Gong, L. Zhang, and C. Yuan, Heteroat. Chem., 14, 13 (2003).

    Article  CAS  Google Scholar 

  10. A. A. Fesenko, D. A. Cheshkov, and A. D. Shutalev, Mendeleev Commun., 18, 51 (2008).

    Article  CAS  Google Scholar 

  11. G. Sabitha, G. S. K. Kumar Reddy, C. S. Reddy, and J. S. Yadav, Synlett, 858 (2003).

  12. J. Azizian, B. Mirza, M. M. Mojtahedi, M. Saeed Abaee, and M. Sargordan, J. Fluorine Chem., 129, 1083 (2008).

    Article  CAS  Google Scholar 

  13. C. O. Kappe, S. F. Falsone, W. M. F. Fabian, and F. Belaj, Heterocycles, 51, 77 (1999).

    Article  CAS  Google Scholar 

  14. V. I. Saloutin, Ya. V. Burgart, O. G. Kuzueva, C. O. Kappe, and O. N. Chupakhin, J. Fluorine Chem., 103, 17 (2000).

    Article  CAS  Google Scholar 

  15. Y. Ma, C. Qian, L. Wang, and M. Yang, J. Org. Chem., 65, 3864 (2000).

    Article  CAS  Google Scholar 

  16. Ya. V. Burgart, O. G. Kuzueva, M. V. Pryadeina, S. O. Kappe, and V. I. Saloutin, Zh. Org. Khim., 37, 915 (2001).

    Google Scholar 

  17. Yu. N. Markitanov, V. M. Timoshenko, and Yu. G. Shermolovich, Zh. Org. Farm. Khim., 8, No. 4 (32), 68 (2010).

    CAS  Google Scholar 

  18. N. Zanatta, D. Faoro, L. da S. Fernandes, P. B. Brondani, D. C. Flores, A. F. C. Flores, H. G. Bonacorso, and M. A. P. Martins, Eur. J. Org. Chem., 5832 (2008).

  19. E. D. Bergmann, S. Cohen, and S. Shahak, J. Chem. Soc. (Resumed), 3278 (1959).

  20. T. E. Nickson, J. Org. Chem., 53, 3870 (1988).

    Article  CAS  Google Scholar 

  21. V. G. Nenaidenko, A. V. Sanin, V. S. Kuz'min, and E. S. Balenklova, Zh. Org. Khim., 32, 1579 (1996).

    CAS  Google Scholar 

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Correspondence to V. M. Timoshenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1191–1197, August, 2011.

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Timoshenko, V.M., Markitanov, Y.N. & Shermolovich, Y.G. Preparation of pyrimidine derivatives through three-component reactions of dialkyl (2-oxo-3,3,3-trifluoropropyl)phosphonates. Chem Heterocycl Comp 47, 977–982 (2011). https://doi.org/10.1007/s10593-011-0863-4

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  • DOI: https://doi.org/10.1007/s10593-011-0863-4

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