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Reactions of hexafluoroacetone benzenesulfonyl- and trifluoroacetylimines with arylamines

  • N. D. Chkanikov
  • V. L. Vershinin
  • M. V. Galakhov
  • A. F. Kolomiets
  • A. V. Fokin
Organic Chemistry

Conclusions

  1. 1.

    Nonsterically hindered primary arylamines react with hexafluoroacetone benzenesulfonyl- and trifluoroacetylimines to give stable gem-diamino compounds.

     
  2. 2.

    The presence of substituents at the nitrogen of the arylamine destabilizes these gem-diamino compounds, with the formation of C2- and C4-alkylation products. With hexafluoroacetone trifluoroacetylimine, C2-alkylation is accompanied by heterocyclization to give 1-substituted 2,4,4-tris(trifluoroacetyl)-1,4-dihydroquinazolines.

     
  3. 3.

    N,N-Dialkylanilines are regioselectively alkylated at C4.

     

Keywords

Nitrogen Arylamines Benzenesulfonyl Trifluoroacetyl Hexafluoroacetone 
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.
    N. D. Chkanikov, V. L. Vershinin, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., 952 (1986).Google Scholar
  2. 2.
    G. F. Il'in, A. F. Kolomiets, and G. A. Sokol'skii, Zh. Vses. Khim. Ova.,25, 109 (1980).Google Scholar
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    N. D. Chkanikov, A. E. Zelenin, M. V. Galakhov, et al., Zh. Org. Khim.,21, 1358 (1985).Google Scholar
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    A. E. Zelenin, N. D. Chkanikov, M. V. Galakhov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 931 (1985).Google Scholar
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    J. Attenborow, A. F. B. Cameron, J. H. Chapman, et al., J. Chem. Soc., 1094 (1952).Google Scholar

Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • N. D. Chkanikov
    • 1
  • V. L. Vershinin
    • 1
  • M. V. Galakhov
    • 1
  • A. F. Kolomiets
    • 1
  • A. V. Fokin
    • 1
  1. 1.A. N. Nesmeyanov Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow

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