Russian Journal of Organic Chemistry

, Volume 41, Issue 7, pp 1036–1042 | Cite as

Reactions of Substituted Ethyl 1,2,3,4,4′,5′-Hexahydrospiro-[naphthalene-2,5′-pyrazole]-3′-carboxylates with Halogens

  • A. P. Molchanov
  • V. S. Korotkov
  • J. Kopf
  • R. R. Kostikov
Article

Abstract

Substituted ethyl 1,2,3,4,4′,5′-hexahydrospiro[naphthalene-2,5′-pyrazole]-3′-carboxylates react with chlorine or N-bromosuccinimide to give spirocyclic substituted 3-halo-4,5-dihydro-3H-pyrazoles which lose nitrogen molecule on heating with formation of substituted spirocyclic 1-halocyclopropane-1-carboxylates. Heating of the title compounds with bromine in acetic acid results in opening of the spiro-fused six-membered ring to afford ethyl 4-aryl-5-[2-(2-carboxyphenyl)ethyl]pyrazole-3-carboxylates.

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REFERENCES

  1. 1.
    Molchanov, A.P., Stepakov, A.V., and Kostikov, R.R., Russ. J. Org. Chem., 2001, vol. 37, p. 128.CrossRefGoogle Scholar
  2. 2.
    Molchanov, A.P., Stepakov, A.V., Kostikov, R.R., and Baird, M.S., Synlett, 2000, p. 219.Google Scholar
  3. 3.
    Molchanov, A.P., Stepakov, A.V., Boitsov, V.M., and Kostikov, R.R., Russ. J. Org. Chem., 2002, vol. 38, p. 1666.CrossRefGoogle Scholar
  4. 4.
    Molchanov, A.P., Stepakov, A.V., and Kostikov, R.R., Russ. J. Org. Chem., 2002, vol. 38, p. 264.CrossRefGoogle Scholar
  5. 5.
    Molchanov, A.P., Stepakov, A.V., Boitsov, V.M., Kopf, J., and Kostikov, R.R., Russ. J. Org. Chem., 2002, vol. 38, p. 1797.CrossRefGoogle Scholar
  6. 6.
    Molchanov, A.P., Stepakov, A.V., Boitsov, V.M., Kopf, J., and Kostikov, R.R., Russ. J. Org. Chem., 2003, vol. 39, p. 108.CrossRefGoogle Scholar
  7. 7.
    Molchanov, A.P., Korotkov, V.S., and Kostikov, R.R., Russ. J. Org. Chem., 2004, vol. 40, p. 470.CrossRefGoogle Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • A. P. Molchanov
    • 1
  • V. S. Korotkov
    • 1
  • J. Kopf
    • 2
  • R. R. Kostikov
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Institut fur anorganische ChemieHamburgGermany

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