Skip to main content
Log in

8-Alkyl[1,2,4]Triazolo[5,1-b]Purines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A novel method has been developed for the synthesis of 8-alkyl[1, 2, 4]triazolo[5,1-b]purines from 6-nitro[1,2,4]triazolo[1,5-a]pyrimidin-7-ones via successive phosphoryl chloride-mediated chloro-desoxygenation, aminodehalogenation, and reduction to give 7-alkylamino-6-amino[1,2,4]triazolo-[1,5-a]pyrimidines. The latter can be cyclized in the presence of formic acid.

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.

Similar content being viewed by others

References

  1. E. J. Corey, B. Czakó, and L. Kürti, Molecules and Medicine, John Wiley & Sons, Hoboken (2007), p. 272.

    Google Scholar 

  2. J. Wirsching, J. Voss, J. Balzarini, and E. De Clercq, Bioorg. Med. Chem. Lett., 10, 1339 (2000).

    Article  CAS  Google Scholar 

  3. A. Jarrahpour, J. Sheikh, I. El Mounsi, H. Juneja, and T. Ben Hadda, Med. Chem. Res., 22, 1203 (2013).

    Article  CAS  Google Scholar 

  4. L. Scagnelli, M. G. Memeo, S. Carosso, B. Bovio, and P. Quadrelli, Eur. J. Org. Chem., 3835 (2013).

  5. D. E. Bergstrom, Unnatural Nucleosides with Unusual Base Pairing Properties. Current Protocols in Nucleic Acid Chemistry, 37:1.4:1.4.1–1.4.32, John Wiley & Sons Inc. (2009). DOI: 10.1002/0471142700.nc0104s37.

  6. R. K. Ujjinamatada, P. Phatak, A. M. Burger, and R. S. Hosmane, J. Med. Chem., 51, 694 (2008).

    Article  CAS  Google Scholar 

  7. S. Nakano, M. Fujii, and N. Sugimoto, J. Nucleic Acids, 2011. http://dx.doi.org/10.4061/2011/967098.

  8. C. Burkholder, W. R. Dolbier, Jr., M. Médebielle, and S. Ait-Mohand, Tetrahedron Lett., 42, 3077 (2001).

    Article  CAS  Google Scholar 

  9. B. Xu, A. Stephens, G. Kirschenheuter, A. F. Greslin, X. Cheng, J. Sennelo, M. Cattaneo, M. L. Zighetti, A. Chen, S.-A. Kim, H. S. Kim, N. Bischofberger, G. Cook, and K. A. Jacobson, J. Med. Chem., 45, 5694 (2002).

    Article  CAS  Google Scholar 

  10. M. Lhassani, O. Chavignon, J.-M. Chezal, J.-C. Teulade, J.-P. Chapat, R. Snoeck, G. Andrei, J. Balzarini, E. De Clercq, and A. Gueiffier, Eur. J. Med. Chem., 34, 271 (1999).

    Article  CAS  Google Scholar 

  11. T. Fonseca, B. Gigante, M. M. Marques, T. L. Gilchrist, and E. De Clercq, Bioorg. Med. Chem., 12, 103 (2004).

    Article  CAS  Google Scholar 

  12. D. Combs, C. M. Langevine, Y. Qiu, and F. C. Zusi, WO Pat. Appl. 2005011609.

  13. L. Cosyn, K. K. Palaniappan, S.-K. Kim, H. T. Duong, Z.-G. Gao, K. A. Jacobson, and S. Van Calenbergh, J. Med. Chem., 49, 7373 (2006).

    Article  CAS  Google Scholar 

  14. L. A. Januar and T. F. Molinski, Org. Lett., 15, 2370 (2013).

    Article  CAS  Google Scholar 

  15. D. González-Rodríguez, P. G. A. Janssen, R. Martín-Rapún, I. De Cat, S. De Feyter, A. P. H. J. Schenning, and E. W. Meijer, J. Am. Chem. Soc., 132, 4710 (2010).

    Article  Google Scholar 

  16. B. C. Bookser and N. B. Raffaele, J. Org. Chem., 72, 173 (2007).

    Article  CAS  Google Scholar 

  17. J.-Q. Wang, Q.-H. Zheng, X. Fei, X. Liu, T. A. Gardner, C. Kao, S. P. Raikwar, B. E. Glick-Wilson, M. L. Sullivan, B. H. Mock, and G. D. Hutchins, Synth. Commun., 34, 917 (2004).

    Article  CAS  Google Scholar 

  18. J.-Q. Wang, Q.-H. Zheng, X. Fei, B. H. Mock, and G. D. Hutchins, Bioorg. Med. Chem. Lett., 13, 3933 (2003).

    Article  CAS  Google Scholar 

  19. Y. Fuchi, Y. Koga, O. Nakagawa, and S. Sasaki, Tetrahedron, 67, 6746 (2011).

    Article  Google Scholar 

  20. A. E. A. Hassan, P. Wang, A. K. Watanabe, R. T. McBrayer, J. M. Otto, J. L. Stuyver, M. P. Tharnish, and F. R. Schinazi, Nucleosides, Nucleotides Nucleic Acids, 24, 961 (2005).

    Article  CAS  Google Scholar 

  21. N. Bomholt, P. T. Jørgensen, and E. B. Pedersen, Bioorg. Med. Chem. Lett., 21, 7376 (2011).

    Article  CAS  Google Scholar 

  22. S. Ikeda, K. Sugizaki, H. Yanagisawa, and A. Okamoto, Org. Biomol. Chem., 9, 4176 (2011).

    Article  Google Scholar 

  23. T. Shiota, T. Yamamori, K. Sakai, M. Kiyokawa, T. Honma, M. Ogawa, K. Hayashi, N. Ishizuka, K. Matsumura, M. Hara, M. Fujimoto, T. Kawabata, and S. Nakajima, Chem. Pharm. Bull., 47, 928 (1999).

    Article  CAS  Google Scholar 

  24. U. Hempel, E. Lippmann, and E. Tenor, Z. Chem., 30, 320 (1990).

    Article  CAS  Google Scholar 

  25. V. L. Rusinov, M. N. Kushnir, and O. N. Chupakhin, Zh. Org. Khim., 27, 2461 (1991).

    Google Scholar 

  26. V. L. Rusinov, E. N. Ulomsky, O. N. Chupakhin, M. M. Zubairov, A. B. Kapustin, N. I. Mitin, M. I. Zhirovetskii, and I. A. Vinogradov, Khim.-Farm. Zh., 24, No. 9, 41 (1990). [Pharm. Chem. J., 24, 646 (1990)].

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. N. Ulomsky.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 953-961, June, 2014.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Savateev, K.V., Ulomsky, E.N., Borisov, S.S. et al. 8-Alkyl[1,2,4]Triazolo[5,1-b]Purines. Chem Heterocycl Comp 50, 880–887 (2014). https://doi.org/10.1007/s10593-014-1542-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-014-1542-z

Keywords

Navigation