Advertisement

Chemistry of Heterocyclic Compounds

, Volume 20, Issue 4, pp 416–421 | Cite as

Diazo carbonyl derivatives of heterocycles. 3. Alternative 1,3-dipolar addition to azidoalkyl α-diazo ketones and synthesis of five-membered heterocycles based on them

  • V. G. Kartsev
  • T. S. Pokidova
  • A. S. Nabatov
  • A. V. Dovgilevich
Article

Abstract

It is shown that the cycloaddition of dimethylacetylenedicarboxylate and N-phenylmaleinimide to azidoalkyl diazomethyl ketones leads to the corresponding 1,2,3-triazole and 2-pyrazoline derivatives. The electronic structure of one of the bisdipoles was determined.

Keywords

Organic Chemistry Carbonyl Ketone Dimethylacetylenedicarboxylate Diazomethyl 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    V. G. Kartsev, S. V. Chapyshev, A. M. Sipyagin, N. A. Yashina, and V. S. Petrosyan, Khim. Geterotsikl. Soedin., No. 8, 1103 (1983).Google Scholar
  2. 2.
    L. L. Rodina, V. V. Bulusheva, and I. K. Korobitsyna, Zh. Org. Khim., 8, 1108 (1972).Google Scholar
  3. 3.
    L. L. Rodina, N. V. Barmenkova, and I. K. Korobitsyna, Zh. Org. Khim., 17, 1899 (1981).Google Scholar
  4. 4.
    G. I. Tsypin, V. V. Mel'nikov, and B. V. Gidaspov, Zh. Org. Khim., 10, 2350 (1974).Google Scholar
  5. 5.
    R. Huisgen, J. Org. Chem., 41., 403 (1976).Google Scholar
  6. 6.
    R. A. Firestone, J. Org. Chem., 37, 2181 (1972).Google Scholar
  7. 7.
    Z. G. Aliev, V. G. Kartsev, L. O. Atovmyan, and G. N. Voronina, Khim. Geterotsikl. Soedin., No. 1, 91 (1982).Google Scholar
  8. 8.
    I. K. Korobitsyna, V. V. Bulusheva, and L. L. Rodina, Khim. Geterotsikl. Soedin., No. 5, 579 (1978).Google Scholar
  9. 9.
    R. Silverstein, G. Bassler, and T. Morrill, Spectrometric Identification of Organic Compounds, Wiley (1974).Google Scholar
  10. 10.
    K. N. Houk, J. Sims, R. E. Duke, and R. W. Stroizier, J. Am. Chem. Soc., 95, 7287 (1973).Google Scholar
  11. 11.
    K. N. Houk, J. Sims, C. R. Watts, and L. J. Luskus, J. Am. Chem. Soc., 95, 7301 (1973).Google Scholar
  12. 12.
    K. N. Houk, J. Am. Chem. Soc., 94, 8953 (1972).Google Scholar
  13. 13.
    G. A. Shchembelov and Yu. A. Ustynyuk, Quantum-Chemical Methods for the Calculation of Molecules [in Russian], Khimiya, Moscow (1977), p. 335.Google Scholar
  14. 14.
    F. Arndt and B. Eistert, Chem. Ber., 68, 200 (1935).Google Scholar

Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • V. G. Kartsev
    • 1
  • T. S. Pokidova
    • 1
  • A. S. Nabatov
    • 1
  • A. V. Dovgilevich
    • 1
  1. 1.Branch of the Institute of Chemical PhysicsAcademy of Sciences of the USSRChernogolovka

Personalised recommendations