Advertisement

Chemistry of Heterocyclic Compounds

, Volume 19, Issue 8, pp 886–889 | Cite as

Diazo carbonyl derivatives of heterocycles. 2. Reaction of anhydrides of pyridine- and quinolinedicarboxylic acids with diazomethane

  • V. G. Kartsev
  • S. V. Chapyshev
  • A. M. Sipyagin
  • N. S. Yashina
  • V. S. Petrosyan
Article
  • 44 Downloads

Abstract

The reaction of anhydrides of cinchomeronic, quinolinic, and acridinic acids with diazomethane was studied. The reaction pathway that they have in common is acylation of diazomethane with opening of the anhydride ring, accompanied by the formation of the corresponding diazo ketones. It is shown that the nature of the heterocyclic part of the anhydride molecule has a substantial effect on the character of the parallel reactions.

Keywords

Organic Chemistry Pyridine Carbonyl Ketone Anhydride 
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.
    S. V. Chapyshev, S. V. Kartsev, and A. M. Sipyagin, Khim. Geterotsikl. Soedin., No. 8, 1098 (1983).Google Scholar
  2. 2.
    F. Arndt, B. Eistert, and W. Partale, Chem. Ber., 60, 1364 (1927).Google Scholar
  3. 3.
    F. Arndt and J. Amende, Chem. Ber., 61, 1122 (1928).Google Scholar
  4. 4.
    L. Horner and H. Schwarz, Ann. Chem., 747, 21 (1971).Google Scholar
  5. 5.
    D. Hodson, G. Holt, and D. K. Wall, J. Chem. Soc., C, No. 7, 971 (1970).Google Scholar
  6. 6.
    A. Bhati, J. Org. Chem., 27, 1183 (1962).Google Scholar
  7. 7.
    P. Mc C. Duggleby and G. Holt, J. Chem. Soc., No. 9, 3579 (1962).Google Scholar
  8. 8.
    A. I. Kol'tsov and B. A. Ershov, Nuclear Magnetic Resonance in Organic Chemistry [Russian translation], Leningrad State University (1968), Leningrad (1968), p. 43.Google Scholar
  9. 9.
    E. Kleinpeter and R. Borsdorf, 13C NMR Spectroscopie in der organischen Chemie, Akademie Verlag, Berlin (1981), p. 14.Google Scholar
  10. 10.
    L. Capuano, Chem. Ber., 92, 2670 (1959).Google Scholar
  11. 11.
    L. Capuano and F. Jamaigne, Chem. Ber., 96, 798 (1963).Google Scholar
  12. 12.
    J. B. Bastus, Tetrahedron Lett., No. 15, 955 (1963).Google Scholar
  13. 13.
    R. Clinging, F. M. Dean, and L. E. Houghton, J. Chem. Soc., C, No. 7, 897 (1970).Google Scholar
  14. 14.
    D. M. Dean and R. S. Johnson, J. Chem. Soc., Perkin Trans. I, No. 1, 224 (1981).Google Scholar
  15. 15.
    B. Fels, Chem. Ber., 37, 2137 (1904).Google Scholar
  16. 16.
    A. M. Dox, J. Am. Chem. Soc., 37, 1948 (1915).Google Scholar
  17. 17.
    L. Hozer and S. V. Niementovski, J. Prakt. Chem., 116, 43 (1927).Google Scholar

Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • V. G. Kartsev
    • 1
    • 2
  • S. V. Chapyshev
    • 1
    • 2
  • A. M. Sipyagin
    • 1
    • 2
  • N. S. Yashina
    • 1
    • 2
  • V. S. Petrosyan
    • 1
    • 2
  1. 1.Branch of the Institute of Chemical PhysicsAcademy of Sciences of the USSRChernogolovka
  2. 2.M. V. Lomonosov Moscow State UniversityMoscow

Personalised recommendations