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N-Heterocyclic Carbenes: XII. Sterically Congested Diterpene Imidazolium and Benzimidazolium Salts

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Abstract

Diterpene derivatives of imidazole and benzimidazole were synthesized by the phase-transfer alkylation of imidazole and benzimidazole with a sterically congested diterpene bromoketone. The corresponding imidazolium and benimidazolium salts were also prepared.

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REFERENCES

  1. Denisov, M.S., Gorbunov, A.A., Myalitzin, Yu.A., Dmitriev, M.V., Slepukhin, P.A., and Glushkov, V.A., Chem. Heterocycl. Compd., 2019, vol. 55, p. 217. https://doi.org/10.1007/s10593-019-02445-1

    Article  CAS  Google Scholar 

  2. Glushkov, V.A., Kotelev, M.S., Rudowsky, K.S., Maiorova, O.A., Tarantin, A.V., and Tolstikov, A.G., Russ. J. Org. Chem., 2009, vol. 45, p. 404. https://doi.org/10.1134/S1070428009030099

    Article  CAS  Google Scholar 

  3. Glushkov, V.A., Valieva, M.S., Maiorova, O.A., Baigacheva, E.V., and Gorbunov, A.A., Russ. J. Org.Chem., 2011, vol. 47, p. 230. https://doi.org/10.1134/S1070428011020114

    Article  CAS  Google Scholar 

  4. Glushkov, V.A., Arapov, K.A., Kotelev, M.S., Rudowsky, K.S., Suponitsky, K.Yu., Gorbumov, A.A., Maiorova, O.A., and Slepukin, P.A., Heteroatom Chem., 2012, vol. 23, p. 5. https://doi.org/10.1002/hc.20745

    Article  CAS  Google Scholar 

  5. Glushkov, V.A., Teplykh, E.N., Denisov, M.S., and Gorbunov, A.A., Russ. J. Org. Chem., 2012, vol. 48, p. 815. https://doi.org/10.1134/S1070428012060115

    Article  CAS  Google Scholar 

  6. Gorbunov, A.A., Denisov, M.S., Karmanov, V.I., and Glushkov, V.A., Russ. J. Org. Chem., 2013, vol. 49, p. 1062. https://doi.org/10.1134/S1070428013070178

    Article  CAS  Google Scholar 

  7. Denisov, M.S., Usatykh, I.S., Gorbunov, A.A., and Maiorova, O.A., Russ. J. Org. Chem., 2014, vol. 50, p. 705. https://doi.org/10.1134/S1070428014050145

    Article  CAS  Google Scholar 

  8. Glushkov, V.A., Zhiguleva, M.A., Maiorova, M.A., and Gorbunov, A.A., Russ. J. Org. Chem., 2012, vol. 48, p. 699. https://doi.org/10.1134/S1070428012050120

    Article  CAS  Google Scholar 

  9. Pavlogradskaya, L.V., Denisov, M.S., Borisova, I.A., Maiorova, O.A., and Glushkov, V.A., Russ. J. Org.Chem., 2016, vol. 52, p. 42. https://doi.org/10.1134/S1070428016010085

    Article  CAS  Google Scholar 

  10. Organ, M.G., Calimsiz, S., Sayah, M., Hoi, K.H., and Lough, A.J., Angew. Chem., Int. Ed., 2006, vol. 48, p. 2383. https://doi.org/10.1002/anie.200805661

    Article  CAS  Google Scholar 

  11. Chartoire, A., Lesieur, M., Favilene, L., Slawin, A.M.Z., Cavallo, L., Cazin, C.S.J., and Nolan, S.P., Chem. Eur.J., 2012, vol. 18, p. 4517. https://doi.org/10.1002/chem.201104009

    Article  CAS  PubMed  Google Scholar 

  12. Pompeo, M., Farmer, J.L., Froese, R.D.J., and Organ, M.G., Angew. Chem., Int. Ed., 2014, vol. 53, p. 3223. https://doi.org/10.1002/anie.201310457

    Article  CAS  Google Scholar 

  13. Atwater, B., Chandrasoma, N., Mitchell, D., Rodriguez, M.J., and Organ, M.G., Chem. Eur. J., 2016, vol. 22, p. 14531. https://doi.org/10.1002/chem.201603603

    Article  CAS  PubMed  Google Scholar 

  14. Diner, C. and Organ, M.G., Organometallics, 2019, vol. 38, p. 66. https://doi.org/10.1021/acs.organomet.8b00818

    Article  CAS  Google Scholar 

  15. Hopkinson, M.N., Richter, C., Schedler, M., and Glorius, F., Nature, 2014, vol. 510, p. 485. https://doi.org/10.1038/nature13384

    Article  CAS  PubMed  Google Scholar 

  16. Hazari, N., Melvin, P.R., and Beromi, M.M., NatureRev. Chem., 2017, vol. 1, p. 15. https://doi.org/10.1038/s41570.017.0025

    Article  Google Scholar 

  17. Hoi, K.H., Çalimzis, S., Froese, R.D.J., Hopkinson, A.C., and Organ, M.G., Chem. Eur. J., 2012, vol. 18, p. 145. https://doi.org/10.1002/chem.201102428

    Article  CAS  PubMed  Google Scholar 

  18. Fieser, L.F. and Cambell, W.P., J. Am. Chem. Soc., 1939, vol. 61, p. 2528. https://doi.org/10.1021/ja01878a080

    Article  CAS  Google Scholar 

  19. Liu, M.-L., Pan, X.-Y., Yang, T., Zhang, W.-M., Wang, T.-Q., Wang, H.-Y, Lin, H.-X., Yang, C.-G., and Cui, Y.-M., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 5492. https://doi.org/10.1016/j.bmcl.2016.10.018

    Article  CAS  PubMed  Google Scholar 

  20. Irismetov, M.P., Tolstikov, G.A., Goryaev, M.I., and Von, G.P., Izv. Akad. Nauk Kaz. SSR, Ser. Khim., 1968, vol. 5, p. 85; Ref. Zh. Khim., 1969, no. 13Zh581.

    Google Scholar 

  21. Gridnev, A. and Mihaltseva, I., Synth. Commun., 1994, vol. 24, p. 1547. https://doi.org/10.1080/00397919408010155

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The work was carried out using the equipment of The Core Facilities Centre “Research of materials and matter” at the PFRC UB RAS. The authors are grateful to Engineer I.A. Borisova for measuring the IR spectra, Leading Engineer O.A. Maiorova for measuring the 1H and 13C NMR spectra, and Researcher A.V. Kharitonova for elemental analysis.

Funding

The work was performed by the state order (project no. AAAA-A18-118030790037-7).

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Authors and Affiliations

  1. Institute of Technical Chemistry, Perm Federal Scientific Centre, Ural Branch, Russian Academy of Sciences, 614013, Perm, Russia

    M. S. Denisov & V. A. Glushkov

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  1. M. S. Denisov
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  2. V. A. Glushkov
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Correspondence to M. S. Denisov.

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The authors declare no conflict of interest.

Additional information

For communication XI, see [1].

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Denisov, M.S., Glushkov, V.A. N-Heterocyclic Carbenes: XII. Sterically Congested Diterpene Imidazolium and Benzimidazolium Salts. Russ J Org Chem 56, 775–780 (2020). https://doi.org/10.1134/S1070428020050085

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