Skip to main content
Log in

Reactions of 3-nitro-2-trihalomethyl-2H-chromenes with indole, N-methylindole, and N-methylpyrrole. Stereoselective synthesis of 4-azolyl-3-nitro-2-trihalomethylchromanes

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Heating of 3-nitro-2-trifluoromethyl-and 3-nitro-2-trichloromethyl-2H-chromenes with indole, N-methylindole, and N-methylpyrrole under solvent-free conditions led with high stereoselectivity and in good yields to cis-trans-3-nitro-2-trifluoromethyl-or trans-cis-3-nitro-2-trichloromethylchromanes substituted by the indol-3-yl (pyrrol-2-yl) fragment in position 4.

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. G. P. Ellis, Chromenes, Chromanones, and Chromones, in The Chemistry of Heterocyclic Compounds, Ed. G. P. Ellis, Wiley, New York, 1977, 31.

    Google Scholar 

  2. W. S. Bowers, T. Ohta, J. S. Cleere, and P. A. Marsella, Science, 1976, 193, 542.

    Article  CAS  Google Scholar 

  3. R. Bergmann and R. Gericke, J. Med. Chem., 1990, 33, 492.

    Article  CAS  Google Scholar 

  4. G. Burrell, F. Cassidy, J. M. Evans, D. Lightowler, and G. Stemp, J. Med. Chem., 1990, 33, 3023.

    Article  CAS  Google Scholar 

  5. R. Gericke, J. Harting, I. Lues, and C. Schittenhelm, J. Med. Chem., 1991, 34, 3074.

    Article  CAS  Google Scholar 

  6. T. Hiyama, Organofluorine Compounds. Chemistry and Application, Springer Verlag, Berlin, 2000.

    Google Scholar 

  7. V. Yu. Korotaev, I. B. Kutyashev, and V. Ya. Sosnovskikh, Heteroatom Chem., 2005, 16, 492.

    Article  CAS  Google Scholar 

  8. V. Yu. Korotaev, V. Ya. Sosnovskikh, I. B. Kutyashev, and M. I. Kodess, Lett. Org. Chem., 2005, 2, 616.

    Article  CAS  Google Scholar 

  9. V. Yu. Korotaev, V. Ya. Sosnovskikh, I. B. Kutyashev, and M. I. Kodess, Izv. Akad. Nauk, Ser. Khim., 2006, 309 [Russ. Chem. Bull., Int. Ed., 2006, 55, 317 (Engl. Transl.)].

  10. V. Yu. Korotaev, V. Ya. Sosnovskikh, I. B. Kutyashev, and M. I. Kodess, Izv. Akad. Nauk, Ser. Khim., 2006, 1945 [Russ. Chem. Bull., Int. Ed., 2006, 55, 2020 (Engl. Transl.)].

  11. V. Yu. Korotaev, I. B. Kutyashev, V. Ya. Sosnovskikh, and M. I. Kodess, Mendeleev Commun., 2007, 17, 52.

    Article  CAS  Google Scholar 

  12. R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1996.

    Google Scholar 

  13. M. Chakrabarty, R. Basak, N. Ghosh, and Y. Harigaya, Tetrahedron, 2004, 60, 1941.

    Article  CAS  Google Scholar 

  14. G. Bartoli, M. Bosco, S. Giuli, A. Giuliani, L. Lucarelli, E. Marcantoni, L. Sambri, and E. Torregiani, J. Org. Chem., 2005, 70, 1941.

    Article  CAS  Google Scholar 

  15. S. Iwata, Y. Ishiguro, M. Utsugi, K. Mitsuhashi, and K. Tanaka, Bull. Chem. Soc. Jpn, 1993, 66, 2432.

    Article  CAS  Google Scholar 

  16. P. K. Singh, A. Bisai, and V. K. Singh, Tetrahedron Lett., 2007, 48, 1127.

    Article  CAS  Google Scholar 

  17. C. Lin, J. Hsu, M. N. V. Sastry, H. Fang, Z. Tu, J.-T. Liu, and Y. Ching-Fa, Tetrahedron, 2005, 61, 11751.

    Article  CAS  Google Scholar 

  18. K. Tanaka and F. Toda, Chem. Rev., 2000, 100, 1025.

    Article  CAS  Google Scholar 

  19. N. Ono, N. Banshou, S. Ito, T. Murashima, and T. Ogawa, J. Heterocycl. Chem., 1997, 34, 1243.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. Ya. Sosnovskikh.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1985–1990, October, 2007.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Korotaev, V.Y., Sosnovskikh, V.Y. & Kutyashev, I.B. Reactions of 3-nitro-2-trihalomethyl-2H-chromenes with indole, N-methylindole, and N-methylpyrrole. Stereoselective synthesis of 4-azolyl-3-nitro-2-trihalomethylchromanes. Russ Chem Bull 56, 2054–2059 (2007). https://doi.org/10.1007/s11172-007-0321-8

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-007-0321-8

Key words

Navigation