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Chemistry of Heterocyclic Compounds

, Volume 27, Issue 6, pp 626–630 | Cite as

Diazabicycloalkanes with nitrogen atoms in the nodal positions. 21. Heteroatom-promoted lithiation of benzo[b]-1,4-diazabicyclo[2.2.2]octene and introduction of substituents into the annelated benzene ring

  • A. A. Gall'
  • A. S. Trachum
  • V. A. Romantsev
  • G. V. Shishkin
Article
  • 36 Downloads

Abstract

The action of n-butyllithium on benzo[b]-1,4-diazabicyclo[2.2.2]octene leads to lithiation in the 3′ position of the aromatic ring. The reaction of this lithium derivative with electrophilic reagents was used to synthesize 3′- and 3′,6′-substituted derivatives of benzo[b]-1,4-diazabicyclo[2.2.2]octene.

Keywords

Nitrogen Lithium Benzene Organic Chemistry Nitrogen Atom 
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.

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Literature Cited

  1. 1.
    E. N. Kuznetsova and G. V. Shishkin, Khim. Geterotsikl. Soedin., No. 1, 97 (1991).Google Scholar
  2. 2.
    A. A. Gall' and G. V. Shishkin, Khim. Geterotsikl. Soedin., No. 9, 1239 (1986).Google Scholar
  3. 3.
    V. Snieckus, J. Heterocycl. Chem., 21, A. Supplemental Issue, Lectures in Heterocyclic Chemistry, 7, 95 (1984).Google Scholar
  4. 4.
    G. Friedmann, P. Linder, M. Brini, and A. Cheminat, J. Org. Chem., 44, 237 (1979).Google Scholar
  5. 5.
    Z. A. Savel'eva, S. V. Larionov, A. A. Gall', A. S. Trachum, G. V. Romanenko, N. V. Podberezskaya, and V. N. Ikorskii, in: Summaries of Papers Presented at the All-Union Conference on the Prospects for the Development of the Chemistry of Skeletal Compounds and Their Use in the National Economy [in Russian], Kuibyshev (1989), p. 130.Google Scholar
  6. 6.
    F. M. Stoyanovich and M. A. Marakatkina, Zh. Org. Khim., 16, 2251 (1980).Google Scholar
  7. 7.
    M. P. Marzocchi, G. Sbrana, and G. Zerbi, J. Am. Chem. Soc., 87, 1429 (1965).Google Scholar
  8. 8.
    G. V. Shishkin and A. A. Gall', Khim. Geterotsilk. Soedin., No. 6, 827 (1980).Google Scholar

Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • A. A. Gall'
    • 1
  • A. S. Trachum
    • 1
  • V. A. Romantsev
    • 1
  • G. V. Shishkin
    • 1
  1. 1.Novosibirsk Institute of Bioorganic Chemistry, Siberian BranchAcademy of Sciences of the USSRNovosibirsk

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