Russian Journal of Organic Chemistry

, Volume 38, Issue 12, pp 1797–1801 | Cite as

Reaction of Substituted 6,8-Dioxo-2,3,7-triazabicyclo[3.3.0]oct-3-ene-4-carboxylates and 6,8-Dioxo-1,2,7-triazaspiro[4.4]non-2-ene-3-carboxylates with N-Fluoropyridinium Tetrafluoroborate

  • A. P. Molchanov
  • A. V. Stepakov
  • V. M. Boitsov
  • J. Kopf
  • R. R. Kostikov
Article

Abstract

Substituted 6,8-dioxo-2,3,7-triazabicyclo[3.3.0]oct-3-ene-4-carboxylates react with N-fluoropyridinium tetrafluoroborate to give mixtures of exo and endo isomers of 6-fluoro-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylates. Analogous reaction of 6,8-dioxo-1,2,7-triazaspiro[4.4]non-2-ene-3-carboxylates results in formation of syn,anti-isomeric 1-fluoro-4,6-dioxo-5-azaspiro[2.4]heptane-1-carboxylates.

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REFERENCES

  1. 1.
    Ishihara, T., Hayashi, K., Ando, T., and Yamanaka, H., J. Org. Chem., 1975, vol. 40, no. 22, pp. 3264-3267.Google Scholar
  2. 2.
    Seyferth, D. and Woodruff, R., J. Org. Chem., 1973, vol. 38, no. 23, pp. 4031-4039.Google Scholar
  3. 3.
    Walborsky, H.M., Allen, L.E., Traenckner, H.J., and Powers, E.J., J. Org. Chem., 1971, vol. 36, no. 20, pp. 2937-2941.Google Scholar
  4. 4.
    Ando, T., Ishihara, T., Yamashita, A., and Matsu-mato, M., Bull. Chem. Soc. Jpn., 1981, vol. 54, no. 12, pp. 3873-3874.Google Scholar
  5. 5.
    Kremlev, M.M., Fialkov, Yu.A., and Yagupol'-skii, L.M., Zh. Org. Khim., 1981, vol. 17, no. 2, pp. 332-337.Google Scholar
  6. 6.
    Molchanov, A.P., Stepakov, A.V., Kostikov, R.R., and Baird, M.S., Synlett, 2000, no. 2, pp. 219-220; Molchanov, A.P., Stepakov, A.V., and Kostikov, R.R., Russ. J. Org. Chem., 2001, vol. 37, no. 1, pp. 128-135.Google Scholar
  7. 7.
    Molchanov, A.P., Stepakov, A.V., and Kostikov, R.R., Russ. J. Org. Chem., 2002, vol. 38, no. 2, pp. 264-268.Google Scholar
  8. 8.
    Ueno, T., Toda, H., Yasunami, M., and Yoshifuji, M., Bull. Chem. Soc. Jpn., 1996, vol. 69, no. 6, pp. 1645-1656.Google Scholar
  9. 9.
    Organic Syntheses, Horning, E.C., Ed., New York: Wiley, 1955, collect. vol. 3. Translated under the title Sintezy organicheskikh preparatov, Moscow: Inostrannaya Literatura, 1952, vol. 3, pp. 475-476.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2002

Authors and Affiliations

  • A. P. Molchanov
    • 1
  • A. V. Stepakov
    • 1
  • V. M. Boitsov
    • 1
  • J. Kopf
    • 2
  • R. R. Kostikov
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Institut für anorganische ChemieHamburgGermany

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