Russian Chemical Bulletin

, Volume 56, Issue 8, pp 1603–1607 | Cite as

Synthesis of 3-R-2-aryl-4,6-dinitroindoles and specific features of their reactions with anionic nucleophiles

  • M. A. Bastrakov
  • A. M. Starosotnikov
  • V. V. Kachala
  • E. N. Nesterova
  • S. A. Shevelev
Article

Abstract

Reaction of different anionic S-nucleophiles with 3-R-2-aryl-4,6-dinitroindoles led to a regiospecific nucleophilic substitution of the nitro group in position 4 with 6-NO2 group remaining intact. The representatives of some peri-annulated polycyclic systems were synthesized on the basis of the substitution products.

Key words

nitro compounds indoles nucleophilic substitution nitro group 

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References

  1. 1.
    R. J. Sundberg, Indoles, Academic Press, San-Diego, 1996.Google Scholar
  2. 2.
    V. V. Rozhkov, A. M. Kuvshinov, V. I. Gulevskaya, I. I. Chervin, and S. A. Shevelev, Synthesis, 1999, 2065.Google Scholar
  3. 3.
    V. M. Vinogradov, I. L. Dalinger, A. M. Starosotnikov, and S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2001, 445 [Russ. Chem. Bull., Int. Ed., 2001, 50, 464].Google Scholar
  4. 4.(a)
    V. M. Vinogradov, A. M. Starosotnikov, and S. A. Shevelev, Mendeleev Commun., 2002, 198; (b) A. M. Starosotnikov, V. V. Kachala, A. V. Lobach, V. M. Vinogradov, and S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2003, 1690 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1782]; (c) A. M. Starosotnikov, A. V. Lobach, and S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2004, 557 [Russ. Chem. Bull., Int. Ed., 2004, 53, 584].Google Scholar
  5. 5.
    I. L. Dalinger, T. I. Cherkasova, and S. A. Shevelev, Tetrahedron Lett., 2001, 42, 8539.CrossRefGoogle Scholar
  6. 6.
    A. M. Starosotnikov, A. V. Lobach, Yu. A. Khomutova, and S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2006, 523 [Russ. Chem. Bull., Int. Ed., 2006, 55, 543].Google Scholar
  7. 7.
    V. V. Rozhkov, A. M. Kuvshinov, and S. A. Shevelev, Heterocyclic Commun., 2000, 6, 525.Google Scholar
  8. 8.
    A. P. Kozikovski, M. N. Greco, and J. P. Springer, J. Am. Chem. Soc., 1982, 104, 7622.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • M. A. Bastrakov
    • 1
  • A. M. Starosotnikov
    • 1
  • V. V. Kachala
    • 1
  • E. N. Nesterova
    • 1
  • S. A. Shevelev
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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