195601-04-8Relevant academic research and scientific papers
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.
Formation of azetidines from schiff bases in the presence of dichlorocarbene generated by thermocatalytic decomposition of sodium trichloroacetate
Khlebnikov,Nikiforova,Kostikov
, p. 707 - 710 (2007/10/03)
The mechanism of formation of 2-azetidinones from Schiff bases under conditions of thermocatalytic decomposition of sodium trichloroacetate was studied by the tracer technique.
Reaction of dihalocarbenes with N-Alkylidene amino acid esters and nitriles. Synthesis of aziridine and pyrrole amino acid derivatives
Khlebnikov,Novikov,Nikiforova,Kostikov
, p. 91 - 99 (2007/10/03)
Conditions for preparation of functionalized geminal dihaloaziridines by reaction of dihalocarbenes with N-benzhydrylidene amino acid esters and nitriles were found. The direction of transformations of the intermediate azomethine ylides depends on the structure of the latter, as deduced from MNDO calculations.
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.
