Chemistry of Heterocyclic Compounds

, Volume 28, Issue 3, pp 299–303 | Cite as

Acetals of lactams and amides of acids. 72. Investigation of reaction of cyclic β-nitroenamines with p-benzoquinone

  • V. M. Lyubchanskaya
  • L. S. Sarkisova
  • L. M. Alekseeva
  • V. G. Granik


The process of condensation of p-benzoquinone with the secondary cyclic enamines 2-(2-nitromethylene)pyrrolidine, -piperidine, and -hexahydroazepine is very much dependent on the size of the saturated ring in these compounds. With increasing ring size, the content of derivatives of 5-hydroxybenzofuran decreases, and the quantity of derivatives of 5-hydroxyindole increases; with the seven-membered enamine, a substituted 6-hydroxyindole is also formed. For enamines of the pyrrolidine and piperidine series, 1,4-bis-2-(2′-nitromethylene)pyrrolidono- or piperidinohydroquinones are also recovered.


Acetal Organic Chemistry Amide Piperidine Lactam 
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Literature cited

  1. 1.
    V. M. Lyubchanskaya, L. M. Alekseeva, and V. G. Granik, Khim. Geterotsikl. Soedin., No. 1, 40 (1992).Google Scholar
  2. 2.
    V. M. Lyubchanskaya and V. G. Granik, Khim. Geterotsikl. Soedin., No. 5, 597 (1990).Google Scholar
  3. 3.
    G. R. Allen, Org. React. (N.Y.), 20, 337 (1973).Google Scholar
  4. 4.
    R. W. Parr and J. A. Reiss, Aust. J. Chem., 37, 1263 (1984).Google Scholar
  5. 5.
    V. G. Granik, A. M. Zhidkova, N. S. Kuryatov, V. P. Pakhomov, and R. G. Glushkov, Khim. Geterotsikl. Soedin., No. 11, 1532 (1973).Google Scholar
  6. 6.
    U. Kucklander, Tetrahedron, 31, 1631 (1975).Google Scholar
  7. 7.
    A. Etienne and Y. Correia, Bull. Soc. Chim. Fr., No. 10, 3704 (1969).Google Scholar
  8. 8.
    S. A. Roman, German Patent 2,321,523; Chem. Abstr., 80, 27110 (1974).Google Scholar
  9. 9.
    S. Petersen, West German Patent 863,058; Chem. Zbl., 8416 (1953).Google Scholar

Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • V. M. Lyubchanskaya
    • 1
  • L. S. Sarkisova
    • 1
  • L. M. Alekseeva
    • 1
  • V. G. Granik
    • 1
  1. 1.Center for the Chemistry of Medicinal SubstancesS. Ordzhonikidze All-Union Scientific-Research Chemical and Pharmaceutical InstituteMoscow

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