Skip to main content
Log in

N-heterocyclic carbenes: VIII. Benzimidazolium diterpene salts with an oxo group in substituent

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

Abstract

Benzimidazolium salts with an oxo group in the substituent are synthesized from a diterpene ketone.

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. Gorbunov, A.A., Denisov, M.S., Karmanov, V.A., and Glushkov, V.A., Russ. J. Org. Chem., 2013, vol. 49, p. 1062.

    Article  CAS  Google Scholar 

  2. Herrmann, W.A., Angew. Chem., Int. Ed., 2002, vol. 41, p. 1290; Kantchev, E.A.B., O’Brien, C.J., and Organ, M.G., Angew. Chem., Int. Ed., 2007, vol. 46, p. 2768; Organ, M.G., Chass, G.A., Fang, D.-C., Hopkinson, A.C., and Valente, C., Synthesis, 2008, p. 2776; Diez-Gonzalez, S., Marion, N., and Nolan, S.P., Chem. Rev., 2009, vol. 109, p. 3612; Fortman, G.C. and Nolan, S.P., Chem. Soc. Rev., 2011, vol. 40, p. 5151; Li, H., Seechurn, C.C.C.J., and Colacot, T.J., ACS Catalysis, 2012, vol. 2, p. 1147.

    Article  CAS  Google Scholar 

  3. Shutz, J. and Herrmann, W.A., J. Organometal. Chem., 2004, vol. 689, p. 2995; Panzner, M.J., Hindi, K.M., Wright, B.D., Taylor, J.B., Han, D.S., Youngs, W.J., and Cannon, C.L., Dalton Trans., 2009, p. 7308.

    Article  Google Scholar 

  4. Shi, J., Lei, N., Tong, Q., Peng, Y., Wei, J., and Jia, L., Eur. J. Inorg. Chem., 2007, p. 2221.

    Google Scholar 

  5. Lee, S. and Hartwig, J.F., J. Org. Chem., 2001, vol. 66, p. 3402; Li, Y., Feng, Z., and You, S.-L., Chem. Commun., 2008, p. 2263; Reddy, P.V.G., Tabassum, S., Blanrue, A., and Wilhelm, R., Chem. Commun., 2009, p. 5910; Malkov, A.V., Stewart-Liddon, A.J.P., Teply, F., Kobr, L., Muir, K.W., Haigh, D., and Kosovsky, P., Tetrahedron, 2008, vol. 64, p. 4011; Schmidt, M.A. and Movassaghi, M., Tetrahedron Lett., 2007, vol. 48, p. 101; Groselj, U., Meden, A., Stanovnik, B., and Svete, J., Tetrahedron: Asymmetry, 2008, vol. 19, p. 330.

    Article  CAS  Google Scholar 

  6. Li, S.-J., Zhong, J.-H., and Wang, Y.-G., Tetrahedron: Asymmetry, 2006, vol. 17, p. 1650.

    Article  CAS  Google Scholar 

  7. Glushkov, V.A., Kotelev, M.S., Rudovskii, K.S., Maiorova, O.A., Tarantin, A.V., and Tosltikov, A.G., Russ. J. Org. Chem., 2009, vol. 45, p. 404; Glushkov, V.A., Arapov, K.A., Kotelev, M.S., Rudowsky, K.S., Suponitsky, K.Yu., Gorbunov, A.A., Maiorova, O.A., and Slepukhin, P.A., Heteroatom. Chem., 2012, vol. 23, p. 5.

    Article  CAS  Google Scholar 

  8. Glushkov, V.A., Zhiguleva, M.A., Maiorova, O.A., and Gorbunov, A.A., Russ. J. Org. Chem., 2012, vol. 48, p. 699.

    Article  CAS  Google Scholar 

  9. 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.

    Article  CAS  Google Scholar 

  10. Glushkov, V.A., Teplykh, E.N., Denisov, M.S., and Gorbunov, A.A., Russ. J. Org. Chem., 2012, vol. 48, p. 815.

    Article  CAS  Google Scholar 

  11. Kuhl, O., Chem. Soc. Rev., 2007, vol. 36, p. 592; Liddle, S.T., Edworthy, I.S., and Arnold, P.L., Chem. Soc. Rev., 2007, vol. 36, p. 1732; John, A. and Ghosh, P., Dalton Trans., 2010, vol. 39, p. 7183; Hahn, F.E., Chem. Cat. Chem., 2013, vol. 5, p. 419; Danopoulos, A.A., Monakhov, K.Yu., and Braunstein, P., Chem. Eur. J., 2013, vol. 19, p. 450.

    Article  Google Scholar 

  12. Ray, L., Barman, S., Shaikh, M.M., and Ghosh, P., Chem. Eur. J., 2008, vol. 14, p. 6646; Kiriyama, M., Shimazawa, R., and Shirai, R., J. Org. Chem., 2008, vol. 73, p. 1597; Turkmen, H., Pape, T., Hahn, F.E., and Çetinkaya B., Eur. J. Inorg. Chem., 2009, p. 285; Liao, C.-Y., Chan, K.-T., Tu, C.-Y., Chang, Y.-W., Hu, C.-H., and Lee, H.M., Chem. Eur. J., 2009, vol. 15, p. 405.

    Article  CAS  Google Scholar 

  13. Hahn, F.E., Wittenbecher, L., Boese, R., and Blaser, D., Chem. Eur. J., 1999, vol. 5, p. 1931; Boydston, A.J., Rice, J.D., Sanderson, M.D., Dykhno, O.L., and Bielawski, C.W., Organometallics, 2006, vol. 25, p. 6087; Huybh, H.V., Holtgrewe, C., Pape, T., Koh, L.L., and Hahn, F.E., Organometallics, 2006, vol. 25, p. 245; Korotkikh, N.I., Rayenko, G.F., Kiselyov, A.V., Knishevitsky, A.V., Shvaika, O.P., Cowley, A.H., Jones, J.N., and Macdonald, C.L.B., Selected Methods for Synthesis and Modification of Heterocycles, Kartsev, V.G., Ed., Moscow: IBS Press, 2002, 1, 220 p.; Korotkikh, N.I., Shvaika, O.P., Rayenko, G.F., Kiselyov, A.V., Knishevitsky, A.V., Cowley, A.H., Jones, J.N., and Macdonald, C.L.B., ARKIVOC, 2005, viii, p. 10; Dogan, O., Ozdemir, Y., Gurbuz, N., and Cetinkaya, B., Heteroatom. Chem., 2008, vol. 19, p. 569; Demir, S., Ozdemir, Y., and Cetinkaya, B., Appl. Organometal. Chem., 2009, vol. 23, p. 520; Tornatzky, J., Kannenberg, A., and Blechert, S., Dalton Trans., 2012, vol. 41, p. 8215.

    Article  CAS  Google Scholar 

  14. Huynh, H.V., Ho, J.H.H., Neo, T.C., and Koh, L.L., J. Organometal. Chem., 2005, vol. 690, p. 3854; Zou, G., Huang, W., Xiao, Y., and Tang, J., New J. Chem., 2006, vol. 30, p. 803; Han, Y., Huynh, H.V., and Koh, L.L., J. Organometal. Chem., 2007, vol. 692, p. 3606.

    Article  CAS  Google Scholar 

  15. Wang, A.-E., Xie, J.-H., Wang, L.-X., and Zhou, Q.-L., Tetrahedron, 2005, vol. 61, p. 259; Wang, R., Zeng, Z., Twamley, B., Piekarski, M.M., and Shreeve, J.M., Eur. J. Org. Chem., 2007, p. 655; Kucukbay, H., Sireci, N., Yilmaz, U., Akkurt, M., Yalcin, S.P., Tahir, M.N., and Ott, H., Appl. Organometal. Chem., 2011, vol. 25, p. 255.

    Article  CAS  Google Scholar 

  16. Schwarz, J., Bolm, V.P.W., Gardiner, M.G., Grosche, M., Herrmann, W.A., Hieringer, W., and Raudaschl-Sieber, G., Chem. Eur. J., 2000, vol. 6, p. 1773; Tessin, U.I., Bantreil, X., Songis, O., and Cazin, C.S.J., Eur. J. Inorg. Chem., 2013, p. 2007.

    Article  CAS  Google Scholar 

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

    Google Scholar 

  18. Starikova, O.V., Dolgushin, G.V., Larina, L.I., Ushakov, P.E., Komarova, T.N., and Lopyrev, V.A., Russ. J. Org. Chem., 2003, vol. 39, p. 1467; Huang, W., Guo, J., Xiao, Y., Zhu, M., Zou, G., and Tang, J., Tetrahedron, 2005, vol. 61, p. 9783.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. A. Glushkov.

Additional information

Original Russian Text © M.S. Denisov, I.S. Usatykh, A.A. Gorbunov, O.A. Maiorova, V.A. Glushkov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 5, pp. 716–721.

For communication VII, see [1].

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Denisov, M.S., Usatykh, I.S., Gorbunov, A.A. et al. N-heterocyclic carbenes: VIII. Benzimidazolium diterpene salts with an oxo group in substituent. Russ J Org Chem 50, 705–710 (2014). https://doi.org/10.1134/S1070428014050145

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428014050145

Keywords

Navigation