ORGN 774 |
| Aziridine-2-carboxylic acid and azetidine-3-carboxylic acid derivatives are biologically and synthetically important amino acid derivatives useful for the preparation of a variety of biologically active nitrogen-containing compounds, proteinogenic and non-proteinogenic amino acids. In this presentation, results are described on the synthesis of alkyl 2-(bromomethyl)aziridine-2-carboxylates 2 and alkyl 3-bromoazetidine-3-carboxylates 3 via amination, bromination, and base-induced cyclization of alkyl 2-(bromomethyl)acrylates 1. The new azaheterocyclic amino acid derivatives, which incorporate the biologically interesting aziridine-2-carboxylate or azetidine-3-carboxylate moiety as well as the synthetically important 2-(halomethyl)aziridine or 3-haloazetidine structural feature, are promising synthetic building blocks as demonstrated by their transformation to a broad range of new biologically interesting aziridine-2-carboxylic esters 4 and azetidine-3-carboxylic esters 5 via nucleophilic substitution with C-, S-, N- and O-nucleophiles.
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Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster
Division of Organic Chemistry |
