Russian Journal of Organic Chemistry

, Volume 39, Issue 4, pp 559–573 | Cite as

Cascade Transformations of (2,2-Diaryl-3,3-dichloroaziridin-1-yl)acetates

  • A. F. Khlebnikov
  • M. S. Novikov
  • E. Yu. Kusei
  • J. Kopf
  • R. R. Kostikov
Article

Abstract

Esters of (2,2-diaryl-3,3-dichloroaziridin-1-yl)acetic acid prepared from glycine derivatives under alkylation conditions afford esters of 2-[N-alkyl-N-(2,2-diaryl-1-cyanovinyl)amino]-3,3-diarylacrylic acid in 20-40% yield. The reaction resulting in these compounds proceeds through a cascade of 3-chloro-2-azadiene and ylide intermediates. 3-Chloro-2-azadienes originating from (2,2-diaryl-3,3-dichloroaziridin-1-yl)acetates react with primary and secondary amines at the carbon atom of imine group providing ketenimines which undergo ketenimine-nitrile rearrangement or fragmentation. The other bases (KOH, MeONa, DBU) effect dehydrochlorination of the mentioned 3-chloro-2-azadienes giving nitrile-ylides which are trapped by nucleophilic reagents. The 3-chloro-2-azadiene obtained from methyl (2,2-diaryl-3,3-dichloroaziridin-1-yl)acetate and DBU was relatively stable and was isolated as an individual compound. (2,2-diaryl-3,3-dichloroaziridin-1-yl)propionates behave as nonfunctionalized dichloroaziridines.

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Copyright information

© MAIK “Nauka/Interperiodica” 2003

Authors and Affiliations

  • A. F. Khlebnikov
    • 1
  • M. S. Novikov
    • 1
  • E. Yu. Kusei
    • 1
  • J. Kopf
    • 2
  • R. R. Kostikov
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Institut fur Anorganische ChemieHamburgGermany

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