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One-Pot Synthesis of 2,9-Bis(halophenyl)-Substituted Perhydrohexaazadibenzotetracenes

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Abstract

A one-pot procedure has been developed for the synthesis of 2,9-bis(halophenyl)-substituted (3bR*,7aR*,10bR*,14aR*)-octadecahydro-1H,8H-2,3a,7b,9,10a,14b-hexaazadibenzo[fg,op]tetracenes by multi­component condensation of trans-1,6,7,12-tetraazaperhydrotetracene with formaldehyde and haloanilines in the presence of YbCl3·6H2O as catalyst.

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REFERENCES

  1. Neumann, P., Aumueller, A., and Trauth, H., US Patent no. 4904779, 1990.

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

    Article  CAS  Google Scholar 

  3. Rakhimova, E.B., Kirsanov, V.Yu., Mescheryakova, E.S., Ibragimov, A.G., and Dzhemilev, U.M., Mendeleev Commun., 2020, vol. 30, p. 308. https://doi.org/10.1016/j.mencom.2020.05.015

    Article  CAS  Google Scholar 

  4. Rakhimova, E.B., Kirsanov, V.Yu., Tret’yakova, E.V., Khalilov, L.M., Ibragimov, A.G., Dzhemileva, L.U., D’yakonov, V.A., and Dzhemilev, U.M., RSC Adv., 2020, vol. 10, p. 21039. https://doi.org/10.1039/D0RA03209C

    Article  CAS  Google Scholar 

  5. Dragoun, M., Gunther, T., Frias, C., Berkessel, A., and Prokop, A., J. Cancer Res. Clin. Oncol., 2018, vol. 144, p. 685. https://doi.org/10.1007/s00432-018-2592-x

    Article  CAS  PubMed  Google Scholar 

  6. Hopff, S.M., Wang, Q., Frias, C., Ahrweiler, M., Wilke, N., Wilke, N., Berkessel, A., and Prokop, A., J. Cancer Res. Clin. Oncol., 2021, vol. 147, p. 2591. https://doi.org/10.1007/s00432-021-03679-3

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Khokhar, A.R., Al-Baker, S., Shamsuddin, S., and Siddik, Z.H., J. Med. Chem., 1997, vol. 40, p. 112. https://doi.org/10.1021/jm960587l

    Article  CAS  PubMed  Google Scholar 

  8. Morales, F., Ramirez, A., Morata-Tarifa, C., Navarro, S.A., Marchal, J.A., Campos, J.M., and Conejo-Garcia, A., Future Med. Chem., 2017, vol. 9, p. 293. https://doi.org/10.4155/fmc-2016-0212

    Article  CAS  PubMed  Google Scholar 

  9. Omer, K.H., Seliman, A.A., Altaf, M., Casagrande, N., Aldinucci, D., Altuwaijri, S., and Isab, A.A., Polyhedron, 2015, vol. 102, p. 773. https://doi.org/10.1016/j.poly.2015.10.029

    Article  CAS  Google Scholar 

  10. Iwanejko, J., Wojaczynska, E., Trynda, J., Maciejew­ska, M., Wietrzyk, J., Kochel, A., and Wojaczynski, J., Tetrahedron, 2017, vol. 73, p. 2276. https://doi.org/10.1016/j.tet.2017.03.017

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  12. Barsegyan, Y.A., Baranov, V.V., Kravchenko, A.N., Strelenko, Y.A., Anikina, L.V., Karnoukhova, V.A., and Kolotyrkina, N.G., Synthesis, 2018, vol. 50, p. 2099. https://doi.org/10.1055/s-0036-1591952

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The spectral studies were performed using the facilities of the Agidel joint center (Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was performed according to the research program of the Institute of Petrochemistry and Catalysis (Ufa Federal Research Center, Russian Academy of Sciences), project no. FMRS-2022-0079 for 2022–2024 (Multicomponent Catalytic Reactions in the Synthesis of Cyclic and Acyclic Heteroatom Compounds). It was financially supported by the Ministry of Science and Higher Education of the Russian Federation (Federal special-purpose program no. 2019-05-595-000-058) and by the President scholarship to young scientists and post-graduate students (project no. SP-197.2019.4).

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 450075, Ufa, Russia

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

Authors
  1. E. B. Rakhimova
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  2. V. Yu. Kirsanov
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  3. A. G. Ibragimov
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Corresponding author

Correspondence to E. B. Rakhimova.

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The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 3, pp. 311–316 https://doi.org/10.31857/S0514749222030090.

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Rakhimova, E.B., Kirsanov, V.Y. & Ibragimov, A.G. One-Pot Synthesis of 2,9-Bis(halophenyl)-Substituted Perhydrohexaazadibenzotetracenes. Russ J Org Chem 58, 322–326 (2022). https://doi.org/10.1134/S1070428022030095

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  • DOI: https://doi.org/10.1134/S1070428022030095

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