Skip to main content
Log in

A new route for the synthesis of substituted 5-amino-4-cyanoimidazol-2-ones – precursors for the preparation of 3,6,7,9-tetrahydro-8H-purin-8-ones derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

5-Alkyl(aryl)amino-4-cyanoimidazol-2-ones were obtained on the basis of 2-alkoxycarbonylamino-3,3-dichloroacrylonitriles. They were then used for the synthesis of derivatives of 3,6,7,9-tetrahydro-8H-purin-8-ones.

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

Similar content being viewed by others

References

  1. O. Diels and A. Gukassianz, Ber., 43, 3317 (1910).

    Google Scholar 

  2. B. S. Drach, E. P. Sviridov, and T. Ya. Lavrenyuk, Zh. Org. Khim., 10, 1271 (1974).

    CAS  Google Scholar 

  3. O. Diels and J. Seib, Ber., 42, 4068 (1909).

    Google Scholar 

  4. B. S. Drach, E. P. Sviridov, A. A. Kisilenko, and A. V. Kirsanov, Zh. Org. Khim., 9, 1818 (1973).

    CAS  Google Scholar 

  5. V. S. Brovarets, S. G. Pil’o, A. N. Chernega, E. A. Romanenko, and B. S. Drach, Zh. Obshch. Khim, 69, 1646 (1999).

    Google Scholar 

  6. J. Perronnet and A. Teche, J. Chem. Res. (S), 44 (1977).

  7. T. Kovac, M. Oklobdzija. G. Comisso, E. Decorte, and T. Fajdiga, J. Heterocycl. Chem., 20, 1339 (1983).

    Article  CAS  Google Scholar 

  8. V. K. Agrawal, S. Sharma, and R. N. Iyer, Indian J. Chem., 20B, 398 (1981).

    CAS  Google Scholar 

  9. K. Kubo, Y. Kohara, E. Imamiya, Y. Sugiura, and Y. Inada, J. Med. Chem., 36, 2182 (1993).

    Article  CAS  Google Scholar 

  10. T. Itaya and T. Harada, Tetrahedron Lett., 23, 2203 (1982).

    Article  CAS  Google Scholar 

  11. T. Itaya and T. Harada, Chem. Pharm. Bull., 38, 2971 (1990).

    CAS  Google Scholar 

  12. T. Itaya, T. Kanai, M. Iwata, and M. Azuma, Chem. Pharm. Bull., 45, 75 (1997).

    CAS  Google Scholar 

  13. M. Bianchi, A. Butti, S. Rossi, F. Barzaghi, and V. Marcaria, Eur. J. Org. Chem., 18, 501 (1983).

    CAS  Google Scholar 

  14. N. N. Smolyar, Kh. Ya. Lopatinskaya, A. B. Vasilechko, D. A. Lomov, and Yu. M. Yutilov, Russ. J. Org. Chem., 43, 417 (2007).

    Article  CAS  Google Scholar 

  15. J. P. Beck, A. G. Arvanitis, M. A. Curry, J. T. Rescinito, and L. W. Fitzgerald, Bioorg. Med. Chem. Lett., 9, 967 (1999).

    Article  CAS  Google Scholar 

  16. M. Rinaldi, P. Pecorari, L. Constantino, A. Provvisionato, M. Malagoli, and C. Cermelli, Farmaco, 47, 1315 (1992).

    CAS  Google Scholar 

  17. D. J. K. Crawford, J. L. Maddocks, D. N. Jones, and P. Szawlowski, J. Med. Chem., 39, 2690 (1996).

    Article  CAS  Google Scholar 

  18. K. Kazaoka, H. Sajiki, and K. Hirota, Chem. Pharm. Bull., 51, 608 (2003).

    Article  CAS  Google Scholar 

  19. K. Nakayama, Biochem. J., 327, 625 (1997).

    CAS  Google Scholar 

  20. F. Bergeron, R. Leduc, and R. Day, J. Mol. Endocrin., 24, 1 (2000).

    Article  CAS  Google Scholar 

  21. G. Thomas, Nat. Rev. Mol. Cell. Biol., 3, 753 (2002).

    Article  CAS  Google Scholar 

  22. V. K. Kibirev, T. V. Osadchuk, and Yu. L. Radavskii, Ukr. Biokhim., Zh., 79, 5 (2007).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. S. Brovarets.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, 410–416, March, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chumachenko, S.A., Shablykin, O.V., Kozachenko, A.P. et al. A new route for the synthesis of substituted 5-amino-4-cyanoimidazol-2-ones – precursors for the preparation of 3,6,7,9-tetrahydro-8H-purin-8-ones derivatives. Chem Heterocycl Comp 47, 336–341 (2011). https://doi.org/10.1007/s10593-011-0762-8

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-011-0762-8

Keywords

Navigation