195601-01-5Relevant articles and documents
Cascade Transformations of (2,2-Diaryl-3,3-dichloroaziridin-1-yl)acetates
Khlebnikov,Novikov,Kusei,Kopf,Kostikov
, p. 559 - 573 (2007/10/03)
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.
A Facile Synthesis of New Ketenimine Derivatives of α-Amino Acids
Khlebnikov, Alexander F.,Novikov, Mikhail S.,Kostikov, Rafael R.
, p. 929 - 930 (2007/10/03)
N-Vinylidene α-amino acid derivatives have been prepared from the benzophenone Schiff bases of α-amino acid esters via dichlorocarbene addition to give gem-dichloroaziridine followed by ring opening and dechlorination.
