Skip to main content
SpringerLink
Log in

Hexahydrohexaazaheptalenobis[1,10-ab]phenalenes — A New Type of Azapolycycles

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

8,17-Disubstituted 8,9,15c,15d,17,18-hexahydro-6b,8,9a,15b,17,18a-hexaazaheptalenobis[1,10-ab]-phenalenes were synthesized for the first time by the reaction of 2,2′,3,3′-tetrahydro-1H,1′H-2,2′-biperimidine with 1,3,5-tricycloalkyl-1,3,5-triazinanes in the presence of NiCl2·6H2O as a catalyst.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

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. Aksenov, A.V., Lyakhovnenko, A.S., Andrienko, A.V., and Levina, Tetrahedron Lett., 2010, vol. 51, p. 2406. doi https://doi.org/10.1016/j.tetlet.2010.02.129

    Article  CAS  Google Scholar 

  2. Aksenov, A.V., Lyakhovnenko, A.S., Spicin, A.N., and Aksenova, I.V., Chem. Heterocycl. Compd., 2011, vol. 47, p. 1180. doi https://doi.org/10.1007/s10593-011-0891-0

    Article  CAS  Google Scholar 

  3. Shcherbakov, S.V., Lobach, D.A., Rubin, M., and Aksenov, A.V., Chem. Heterocycl. Compd., 2014, vol. 50, p. 757. doi https://doi.org/10.1007/s10593-014-1531-2

    Article  CAS  Google Scholar 

  4. Aksenov, A.V., Shcherbakov, S.V., Lobach, D.A., Letichevskaya, N.N., and Vasil’eva, E.A., Chem. Heterocycl. Compd., 2014, vol. 50, p. 677. doi https://doi.org/10.1007/s10593-014-1520-5

    Article  CAS  Google Scholar 

  5. Shcherbakov, S.V., Lobach, D.A., and Aksenov, A.V., Chem. Heterocycl. Compd., 2014, vol. 50, p. 300. doi https://doi.org/10.1007/s10593-014-1476-5

    Article  CAS  Google Scholar 

  6. Pozharskii, A.F. and Dal’nikovskaya, V.V., Russ. Chem. Rev., 1981, vol. 50, p. 816. doi https://doi.org/10.1070/RC1981v050n09ABEH002688

    Article  Google Scholar 

  7. Stafforst, T. and Stadler, J.M., Angew. Chem., Int. Ed., 2013, vol. 52, p. 12448. doi https://doi.org/10.1002/anie.201306150

    Article  CAS  Google Scholar 

  8. Vostrowsky, O. and Hirsch, A., Chem. Rev., 2006, vol. 106, p. 5191. doi https://doi.org/10.1021/cr050561e

    Article  CAS  Google Scholar 

  9. Rakhimova, E.B., Ismagilov, R.A., Meshcheryakova, E.S., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron Lett., 2014, vol. 55, p. 6367. doi https://doi.org/10.1016/j.tetlet.2014.09.122

    Article  CAS  Google Scholar 

  10. Rakhimova, E.B., Kirsanov, V.Yu., Zainullin, R.A., Ibragimov, A.G., and Dzhemilev, U.M., Hindawi J. Chem., 2016, Article ID 8406172. doi https://doi.org/10.1155/2016/8406172

    Article  Google Scholar 

  11. Rakhimova, E.B., Kirsanov, V.Yu., Meshcheryakova, E.S., Khalilov, L.M., Kutepov, B.I., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron, 2017, vol. 73, p. 6880. doi https://doi.org/10.1016/j.tet.2017.10.048

    Article  CAS  Google Scholar 

  12. Rakhimova, E.B., Kirsanov, V.Yu., Meshcheryakova, E.S., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Synlett., 2018, vol. 29, p. 1861. doi https://doi.org/10.1055/s-0037-1610201

    Article  CAS  Google Scholar 

  13. Rakhimova, E.B., Kirsanov, V.Yu., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2018, vol. 54, p. 1085. doi https://doi.org/10.1134/S1070428018070199

    Article  CAS  Google Scholar 

  14. Ji, D. and Sun, J., Org. Lett., 2018, vol. 20, p. 2745. doi https://doi.org/10.1021/acs.orglett.8b00951

    Article  CAS  Google Scholar 

  15. Zhu, C., Xu, G., and Sun, J., Angew. Chem., Int. Ed., 2016, vol. 55, p. 11867. doi https://doi.org/10.1002/anie.201606139

    Article  CAS  Google Scholar 

  16. Peng, S., Cao, S., and Sun, J., Org. Lett., 2017, vol. 19, p. 524. doi https://doi.org/10.1021/acs.orglett.6b03691

    Article  CAS  Google Scholar 

  17. Garve, L.K.B., Jones, P.G., and Werz, D.B., Angew. Chem., Int. Ed., 2017, vol. 56, p. 9226. doi https://doi.org/10.1002/anie.201704619

    Article  CAS  Google Scholar 

  18. Pozharskii, A.F. and Starshikov, N.M., Chem. Heterocycl. Compd., 1978, vol. 14, p. 1156. doi https://doi.org/10.1007/BF00469962

    Article  Google Scholar 

  19. Pozharskii, A.F., Russ. Chem. Rev., 1998, vol. 67, p. 1. doi https://doi.org/10.1070/RC1998v067n01ABEH000377

    Article  Google Scholar 

  20. Pozharskii, A.F., Ozeryanskii, V.A., and Filatova, E.A., Chem. Heterocycl. Compd., 2012, vol. 48, p. 200. doi https://doi.org/10.1007/s10593-012-0983-5

    Article  CAS  Google Scholar 

  21. Pukhovskaya, S.G., Ivanova, Yu.B., Semekin, A.S., and Golubchikov, O.A., Makrogeterotsykly, 2018, vol. 11, p. 13. doi https://doi.org/10.6060/mhc180167p

    Google Scholar 

  22. Mokrov, G.V., Likhosherstov, A.M., Lezina, V.P., Gudasheva, T.A., Bushmarinov, I.S., and Antipin, M.Yu., Russ. Chem. Bull., Int. Ed., 2010, vol. 59, p. 1254. doi https://doi.org/10.1007/s11172-010-0230-0

    Article  CAS  Google Scholar 

  23. Krohn, K. and Cludius-Brandt, S., Synthesis, 2010, vol. 8, p. 1344. doi https://doi.org/10.1055/s-0029-1218658

    Article  Google Scholar 

  24. Kukushkin, Yu.N., Reaktsionnaya sposobnost’ koordinatsionnykh soedinenii, Leningrad: Khimiya, 1987.

    Google Scholar 

Download references

Acknowledgments

Analyses were performed using the equipment of the “Agidel” Center for Collective Use, Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences (IPC UFRC RAS).

Funding

This work was carried out in accordance with the research plans of the IPC UFRC RAS on the topic “Metallocomplex and Heterogeneous Catalysis in the Design of Macroheterocycles and Heteroatomic Compounds” (State Registration no. AAAA-A19-119022290010-9 (2019–2021), as well as with financial support from the Russian Foundation for Basic Research (project no. 18-33-00528-mol_a) and Scholarships of the President of the Russian Federation for young scientists and graduate students (SP-197.2019.4).

Author information

Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, Republic Bashkortostan, 450075, Russia

    E. B. Rakhimova, V. Yu. Kirsanov, A. G. Ibragimov & U. M. Dzhemilev

Authors
  1. E. B. Rakhimova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. Yu. Kirsanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. G. Ibragimov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. U. M. Dzhemilev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. B. Rakhimova.

Additional information

Conflict of Interest

The authors declare no conflict of interest.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 8, pp. 1188–1192.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rakhimova, E.B., Kirsanov, V.Y., Ibragimov, A.G. et al. Hexahydrohexaazaheptalenobis[1,10-ab]phenalenes — A New Type of Azapolycycles. Russ J Org Chem 55, 1099–1102 (2019). https://doi.org/10.1134/S1070428019080074

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428019080074

Keywords

Search

Navigation