Base-catalysed reactions of α-bromo-N-benzyl-propionamide and -isobutyramide. Formation of 2-amino-oxazolidinones

Abstract

α-Bromo-N-benzyl-propionamide and -isobutyramide react with sodium hydride yielding 2-amino-oxazolidinones. Dioxopiperazines are formed only from the halogeno-propionamide. The structure and stereochemistry of a 2-amino-oxazolidinone have been demonstrated by an X-ray crystal analysis. A cycloaddition onto an amide carbonyl is suggested in order to explain the formation of the oxazolidinone derivatives.