Advertisement

Russian Journal of Organic Chemistry

, Volume 55, Issue 6, pp 818–823 | Cite as

Synthesis of New 3-(Alkylsulfanyl)pyrano[3,4-c]-[1,2,4]triazolo[4,3-a]pyridines

  • E. G. Paronikyan
  • Sh. Sh. DashyanEmail author
  • R. G. Paronikyan
Review
  • 16 Downloads

Abstract

A new method has been developed for the synthesis of 8-hydrazinylpyrano[3,4-c]pyridines via pyridine ring rearrangement. New 3-(alkylsulfanyl)pyrano[3,4-c][1,2,4]triazolo[4,3-a]pyridines have been obtained.

Keywords

8-hydrazinylpyrano[3,4-c]pyridines rearrangement triazolo[4,3-a]pyridines pyrano[3,4-c][1,2,4]-triazolo[4,3-a]pyridines S-alkyl derivatives 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

Funding

This study was performed under financial support by the State Science Committee of the Ministry of Education and Science of Armenia (project no. 18T-1D066).

References

  1. 1.
    East, S.P., White, C.B., Barker, O., Barker, S., Bennett, J., Brown, D., Boyd, E.A., Brennan, Ch., Chowdhury, Ch., Collins, I., Convers-Reignier, E., Dymock, B.W., Fletcher, R., Haydon, D.J., Gardiner, M., Hatcher, S., Ingram, P., Lancett, P., Mortenson, P., Papadopoulos, K., Smee, C., Thomaides-Brears, H.B., Tye, H., Workman, J., and Czaplewski, L.G., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 894. doi  https://doi.org/10.1016/j.bmcl.2008.11.102 CrossRefPubMedGoogle Scholar
  2. 2.
    Guba, W., Nettekoven, M., Pullmann, B., Riemer, C., and Schmidt, S., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 3307. doi  https://doi.org/10.1016/j.bmcl.2004.03.104 CrossRefPubMedGoogle Scholar
  3. 3.
    Dugan, B.J., Gingrich, D.E., Mesaros, E.F., Milkiewicz, K.L., Curry, M.A., Zulli, A.L., Dobrzanski, P., Serdikoff, C., Jan, M., Angeles, T.S., Albom, M.S., Mason, J.L., Aimone, L.D., Meyer, Sh.L., Huang, Z., Wells-Knecht, K.J., Ator, M.A., Ruggeri, B.A., and Dorsey, B.D., J. Med. Chem., 2012, vol. 55, p. 5243. doi  https://doi.org/10.1021/jm300248q CrossRefPubMedGoogle Scholar
  4. 4.
    Coupland, C., Hill, T., Morriss, R., Moore, M., Arthur, A., and Hippisley-Cox, J., BMC Med., 2018, vol. 16, p. 1. doi  https://doi.org/10.1186/s12916-018-1022-x CrossRefGoogle Scholar
  5. 5.
    Kamal, A.M., Radval, S.M., and Zaki, R.M., Eur. J. Med. Chem., 2011, vol. 46, p. 567. doi  https://doi.org/10.1016/j.ejmech.2010.11.036 CrossRefPubMedGoogle Scholar
  6. 6.
    Zaki, R.M., El Dean, A.M.K., El Monem, M.I.A., and Seddik, M.A., Heterocycl. Commun., 2016, vol. 22, p. 103. doi  https://doi.org/10.1515/hc-2015-0204 CrossRefGoogle Scholar
  7. 7.
    Kumar, N.V. and Mashelkar, U.C., Heterocycl. Commun., 2007, vol. 13, p. 211. doi  https://doi.org/10.1515/HC.2007.13.4.211 Google Scholar
  8. 8.
    Kumar, N.V. and Mashelkar, U.C., Indian J. Chem., Sect. B, 2008, vol. 47, p. 764. doi  https://doi.org/10.1002/chin.200836159 Google Scholar
  9. 9.
    Noravyan, A.S., Mkrtchyan, A.P., Dzhagatspanyan, I.A., Akopyan, R.A., Akopyan, R.A., and Vartanyan, S.A., Pharm. Chem. J., 1977, vol. 11, p. 1195. doi  https://doi.org/10.1007/BF00777734 CrossRefGoogle Scholar
  10. 10.
    Paronikyan, E.G., Dashyan, Sh.Sh., Noravyan, A.S., Tamazyan, R.A., Ayvazyan, A.G., and Panosyan, H.A., Tetrahedron, 2015, vol. 71, p. 2686. doi  https://doi.org/10.1016/j.tet.2015.03.040 CrossRefGoogle Scholar
  11. 11.
    Paronikyan, E.G., Dashyan, Sh.Sh., Minasyan, N.S., Stepanyan, G.M., Ayvazyan, A.G., and Tamazyan, R.A., Chem. Heterocycl. Compd., 2016, vol. 52, p. 1078. doi  https://doi.org/10.1007/s10593-017-2009-9 CrossRefGoogle Scholar
  12. 12.
    Karataeva, F.N. and Klochkov, V.V., Spektroskopiya YaMR v organicheskoi khimii (NMR Spectroscopy in Organic Chemistry), Kazan: Kazan. Fed. Univ., 2013, vol. 1, p. 49.Google Scholar
  13. 13.
    Pozharskii, A.F., Teoreticheskie osnovy khimii geterotsiklov (Theoretical Foundations of the Chemistry of Heterocycles), Moscow: Khimiya, 1985, p. 159.Google Scholar
  14. 14.
    Drug Discovery and Evaluation: Pharmacological Assays, Vogel, H.G., Ed., Berlin: Springer, 2008, 3rd ed., p. 565.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • E. G. Paronikyan
    • 1
  • Sh. Sh. Dashyan
    • 1
    Email author
  • R. G. Paronikyan
    • 1
  1. 1.Mnjoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical ChemistryNational Academy of Sciences of ArmeniaYerevanArmenia

Personalised recommendations