- Cascade Transformations of (2,2-Diaryl-3,3-dichloroaziridin-1-yl)acetates
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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.
- Khlebnikov,Novikov,Kusei,Kopf,Kostikov
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p. 559 - 573
(2007/10/03)
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- Reaction of dihalocarbenes with N-Alkylidene amino acid esters and nitriles. Synthesis of aziridine and pyrrole amino acid derivatives
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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.
- Khlebnikov,Novikov,Nikiforova,Kostikov
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- A Facile Synthesis of New Ketenimine Derivatives of α-Amino Acids
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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.
- Khlebnikov, Alexander F.,Novikov, Mikhail S.,Kostikov, Rafael R.
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p. 929 - 930
(2007/10/03)
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