Advertisement

Chemistry of Heterocyclic Compounds

, Volume 27, Issue 1, pp 80–83 | Cite as

Diazabicycloalkanes with nitrogen atoms in bridgehead positions 20. Synthesis of naphtho[2,3-b]-1,4-diazabicyclo[2.2.2]octene

  • E. N. Kuznetsova
  • G. C. Shishkin
Article
  • 58 Downloads

Abstract

Reaction of 2-acetamido-3-bis(2-hydroxyethyl)aminonaphthalene with phosphorus oxychloride leads to the formation of 2-methyl-1-(2-chloroethyl)naphtho[2,3-d]imidazole, while reaction with hydrobromic acid gives naphtho[23-b]-1,4-diozabicyclo[2.2.2]octane in 13% yield. The yield of the latter can be increased to 45% by exchange of the hydroxyl groups in the starting material by chlorine and by deacetylation.

Keywords

Nitrogen Phosphorus Hydroxyl Organic Chemistry Chlorine 
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.
    N. P. Luk'yanchuk, V. N. Sil'nikov, and G. V. Shishkin,Khim. Geterotsikl. Soedin., No. 8, 1106 (1989).Google Scholar
  2. 2.
    G. V. Shishkin and G. A. Zloba, USSR Author's Certificate No. 749,835;Byull. Izobret., No. 27, 101 (1980).Google Scholar
  3. 3.
    G. V. Shishkin and A. A. Gall',Khim. Geterotsikl. Soedin., No. 6, 827 (1980).Google Scholar
  4. 4.
    G. A. Shishkin and A. A. Gall',Khim. Geterotsikl. Soedin., No. 6, 831 (1980).Google Scholar
  5. 5.
    G. V. Shishkin,Khim. Geterotsikl. Soedin., No. 10, 1407 (1984).Google Scholar
  6. 6.
    Yu. Kirchne,Thin Layer Chromatography [Russian translation], Mir, Moscow (1981), Vol. 1, p. 463.Google Scholar
  7. 7.
    F. Sachs,Ber.,39, 3022 (1906).Google Scholar

Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • E. N. Kuznetsova
    • 1
  • G. C. Shishkin
    • 1
  1. 1.Institute of Bioorganic Chemistry, Siberian BranchAcademy of Sciences of the USSRNovosibirsk

Personalised recommendations