Skip to main content
SpringerLink
Log in

Chlorination of 2-substituted 1-hydroxyindoles

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Chlorination of 1-hydroxyindole-5,6-dicarbonitriles and 1-hydroxypyrrolo[3,4-f]indole-5,7(1H,6H)-diones with N-chlorosuccinimide afforded previously unknown 3,3-dichloro-3Hindole 1-oxides instead of the expected 3-chloro-1-hydroxyindoles. The latter, however, were prepared in good yields by treatment of the above 3,3-dichloro-3H-indole 1-oxides with piperidine in ethanol. Reduction of 3,3-dichloro-5,6-dicyano-3H-indole 1-oxides with Zn in AcOH yielded the corresponding 3-chloroindole-5,6-dicarbonitriles.

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. Zh. V. Chirkova, M. V. Kabanova, S. I. Filimonov, I. G. Abramov, A. Petzer, J. P. Petzer, K. Yu. Suponitsky, Bioorg. Med. Chem. Lett., 2016, 26: 2214.

    Article  CAS  PubMed  Google Scholar 

  2. Zh. V. Chirkova, M. V. Kabanova, S. I. Filimonov, I. G. Abramov, A. Petzer, J. P. Petzer, S. I. Firgang, K. Yu. Suponitsky, Bioorg. Med. Chem. Lett., 2015, 25: 1206.

    Article  CAS  PubMed  Google Scholar 

  3. D. Kim, M.-S. Kang, K. Song, S. O. Kang, J. Ko, Tetrahedron, 2008, 64: 10417.

    Article  CAS  Google Scholar 

  4. P. Anbarasan, T. Schareina, M. Beller, Chem. Soc. Rev., 2011, 40: 5049.

    Article  CAS  PubMed  Google Scholar 

  5. J. Yan, T. Ni, F. Yan, Tetrahedron Lett., 2015, 56: 1096.

    Article  CAS  Google Scholar 

  6. X. Jiang, J. Yang, F. Zhang, P. Yu, P. Yi, Y. Sun, Y. Wang, Adv. Synth. Catal., 2016, 358: 2678.

    Article  CAS  Google Scholar 

  7. K. L. Erickson, M. R. Brennan, P. A. Namnum, Synth. Commun., 1981, 11: 253.

    Article  CAS  Google Scholar 

  8. C. C. Silveira, S. R. Mendes, L. Wolf, G. M. Martins, L. von Mühlen, Tetrahedron, 2012, 68: 10464.

    Article  CAS  Google Scholar 

  9. T. Guney, J. J. Lee, G. A. Kraus, Org. Lett., 2014, 16: 1124.

    Article  CAS  PubMed  Google Scholar 

  10. R. C. Samanta, H. Yamamoto, Chem. Eur. J., 2015, 21: 11976.

    Article  CAS  PubMed  Google Scholar 

  11. T. Maibunkaew, C. Thongsornkleeb, J. Tummatorn, A. Bunrit, S. Ruchirawat, Synlett, 2014, 25: 1769.

    Article  CAS  Google Scholar 

  12. S. Gabriel, W. Gerhard, R. Wolter, Berichte, 1923, 56: 1024.

    Google Scholar 

  13. T. Nagayoshi, S. Saeki, M. Hamana, Chem. Pharm. Bull., 1984, 32: 3678.

    Article  CAS  Google Scholar 

  14. K. Goerlitzer, K. Ventzke-Neu, Pharmazie, 1998, 53: 19.

    CAS  Google Scholar 

  15. Zh. V. Chirkova, S. I. Filimonov, Russ. Chem. Bull., 2017, 66: 379.

    Article  CAS  Google Scholar 

  16. T. Nagayoshi, S. Saeki, M. Hamana, Chem. Pharm. Bull., 1981, 29: 1920.

    Article  CAS  Google Scholar 

  17. Zh. V. Chirkova, M. V. Kabanova, S. I. Filimonov, I. G. Abramov, A. V. Samet, G. A. Stashina, Mendeleev Commun., 2017, 27: 498.

    Article  CAS  Google Scholar 

  18. J. Slätt, J. Bergman, Tetrahedron, 2002, 58: 9187.

    Article  Google Scholar 

  19. A. Marfat, M. P. Carta, Tetrahedron Lett., 1987, 28: 4027.

    Article  CAS  Google Scholar 

  20. A. E. Shchekotikhin, Y. N. Luzikov, Y. B. Sinkevich, V. N. Buyanov, M. N. Preobrazhenskaya, Chem. Heterocycl. Compd., 2008, 44: 1245.

    Article  CAS  Google Scholar 

  21. S. I. Filimonov, Zh. V. Chirkova, V. S. Sharunov, I. G. Abramov, G. A. Stashina, S. I. Firgang, K. Yu. Suponitsky, Chem. Heterocycl. Compd., 2012, 48: 427.

    Article  CAS  Google Scholar 

  22. Zh. V. Chirkova, M. V. Kabanova, S. S. Sergeev, S. I. Filimonov, I. G. Abramov, A. V. Samet, K. Yu. Suponitsky, Mendeleev Commun., 2015, 25: 315.

    Article  CAS  Google Scholar 

  23. N. de Kimpe, C. Stevens, J. Org. Chem., 1993, 58: 2904.

    Article  Google Scholar 

  24. L. van der Wolf, H. J. J. Pabon, Rec. Trav. Chim., 1977, 96: 72.

    Article  CAS  Google Scholar 

  25. R. Bloch, Synthesis, 1978, 140.

  26. T. Hata, Bull. Chem Soc. Jpn, 1964, 37: 547.

    Article  CAS  Google Scholar 

  27. Zh. V. Chirkova, M. V. Kabanova, S. I. Filimonov, I. G. Abramov, A. V. Samet, G. A. Stashina, K. Yu. Suponitsky, Tetrahedron Lett., 2017, 58: 755.

    Article  CAS  Google Scholar 

  28. S. I. Filimonov, Zh. V. Chirkova, I. G. Abramov, S. I. Firgang, G. A. Stashina, Y. A. Strelenko, D. V. Khakimov, T. S. Pivina, A. V. Samet, K. Y. Suponitsky, Tetrahedron, 2012, 68: 5991.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Yaroslavl State Technical University, 88 Moskovskii prosp., 150023, Yaroslavl, Russian Federation

    Zh. V. Chirkova, M. V. Kabanova, S. I. Filimonov & T. N. Sudzilovskaya

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. V. Samet & G. A. Stashina

Authors
  1. Zh. V. Chirkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. V. Kabanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. I. Filimonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Samet
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. G. A. Stashina
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. T. N. Sudzilovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zh. V. Chirkova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1083–1087, June, 2018.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chirkova, Z.V., Kabanova, M.V., Filimonov, S.I. et al. Chlorination of 2-substituted 1-hydroxyindoles. Russ Chem Bull 67, 1083–1087 (2018). https://doi.org/10.1007/s11172-018-2184-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-018-2184-6

Key words

Search

Navigation