Synthesis of new functionalized aziridine-2- and azetidine-3-carboxylic acid derivatives

ORGN 774

Sven Mangelinckx1, Asta Zukauskaite2, Vida Buinauskaite2, Algirdas Sackus2, and Norbert De Kimpe1. (1) Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium, (2) Department of Organic Chemistry, Faculty of Chemical Technology, Kaunas University of Technology, Radvilenu pl.19, Lithuania, LT-50270 Kaunas, Lithuania
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.