Skip to main content
SpringerLink
Log in

Synthesis of 7-bromo, 7-phenylethynyl, 7-azido, and 7-nitro derivatives of N-acetyl-1,3a,4,8b-tetrahydrocyclopenta[b]indole

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

Abstract

7-Bromo-, 7-phenylethynyl-, 7-azido-, 7-nitro-, and 5,7-dinitro-substituted N-acetyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles have been synthesized starting from anilines and 3-chlorocyclopentene. The NMR spectra of N-acetyl-7-nitro-1,3a,4,8b-tetrahydrocyclopenta[b]indoles displayed no signal doubling typical of the other 7-substituted derivatives.

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. Horiuchi, T., Miura, H., and Uchida, S., Chem. Commun., 2003, p. 3036.

    Google Scholar 

  2. Bhattacharya, C., Bonfante, P., Deagostino, A., Kapulnik, Y., Larini, P., Occhiato, E.G., Prandi, C., and Venturello, P., Org. Biomol. Chem., 2009, vol. 7, p. 3413.

    Article  CAS  Google Scholar 

  3. Dentani, T., Kubota, Y., Funabiki, K., Jin, J., Yoshida, T., Minoura, H., Miura, H., and Matsui, M., New J. Chem., 2009, vol. 33, p. 93.

    Article  CAS  Google Scholar 

  4. Higashijima, S., Miura, H., Fujita, T., Kubota, Y., Funabiki, K., Yoshida, T., and Matsui, M., Tetrahedron, 2011, vol. 67, p. 6289.

    Article  CAS  Google Scholar 

  5. Barishnikov, G.V., Minaev, B.P., and Minaeva, V.O., Visn. Cherkas. Univ., 2010, no. 174, p. 33.

    Google Scholar 

  6. Ratni, H., Blum-Kaelin, D., Dehmlow, H., Hartman, P., Jablonski, P., Masciadri, R., Maugeais, C., Patiny-Adam, A., Panday, N., and Wright, M., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 1654.

    Article  CAS  Google Scholar 

  7. Zhang, X., Lanter, J.C., and Sui, Z., Expert Opin. Ther. Patents, 2009, vol. 19, p. 1239.

    Article  CAS  Google Scholar 

  8. Gataullin, R.R., Likhacheva, N.A., Suponitskii, K.Yu., and Abdrakhmanov, I.B., Russ. J. Org. Chem., 2007, vol. 43, p. 1310.

    Article  CAS  Google Scholar 

  9. Kong, D.-L., He, L.-H., and Wang, J.-Q., Catal. Commun., 2010, vol. 11, p. 992.

    Article  CAS  Google Scholar 

  10. Bernard, A., Kumar, A., Jamir, L., Sinha, D., and Sinha, U.B., Acta Chim. Slov., 2009, vol. 56, p. 457.

    CAS  Google Scholar 

  11. Zhu, W. and Ma, D., Chem. Commun., 2004, p. 888.

    Google Scholar 

  12. Jiang, L., Lu, X., Zhang, H., Jiang, Y., and Ma, D., J. Org. Chem., 2009, vol. 74, p. 4542.

    Article  CAS  Google Scholar 

  13. Tolstikov, G.A., Mustafin, A.G., Gataullin, R.R., and Abdrakhmanov, I.B., Izv. Akad. Nauk, Ser. Khim., 1992, p. 1449.

    Google Scholar 

  14. Skladchikov, D.A., Suponitskii, K.Yu., Abdrakhmanov, I.B., and Gataullin, R.R., Russ. J. Org. Chem., 2012, vol. 48, p. 957.

    Article  CAS  Google Scholar 

  15. Skladchikov, D.A., Buranbaeva, R.S., Fatykhov, A.A., Ivanov, S.P., and Gataullin, R.R., Russ. J. Org. Chem., 2012, vol. 48, p. 1550.

    Article  CAS  Google Scholar 

  16. Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 2. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1983, vol. 4, p. 426.

    Google Scholar 

  17. Eliel, E.L., Wilen, S.H., and Doyle, M.P., Basic Organic Stereochemistry, New York: Wiley, 2001. Translated under the title Osnovy organicheskoi stereokhimii, Moscow: Binom, 2007, p. 355.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    D. A. Skladchikov, A. A. Fatykhov & R. R. Gataullin

Authors
  1. D. A. Skladchikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. A. Fatykhov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. R. Gataullin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. R. Gataullin.

Additional information

Original Russian Text © D.A. Skladchikov, A.A. Fatykhov, R.R. Gataullin, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 1, pp. 55–60.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Skladchikov, D.A., Fatykhov, A.A. & Gataullin, R.R. Synthesis of 7-bromo, 7-phenylethynyl, 7-azido, and 7-nitro derivatives of N-acetyl-1,3a,4,8b-tetrahydrocyclopenta[b]indole. Russ J Org Chem 50, 48–53 (2014). https://doi.org/10.1134/S1070428014010096

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428014010096

Keywords

Search

Navigation