Synthesis and Transformations of Oxazolidin-2-ones of the Adamantane Series

An efficient one-step synthesis of previously unknown oxazolidin-2-one derivatives containing an adamantane moiety at the C-5 position of the heterocycle was achieved by reacting bromomethyloxiranes of the adamantane series with primary amines in the presence of potassium carbonate. The reaction proceeds through successive stages of nucleophilic substitution and intramolecular cyclization, providing the target products in yields of 40–80%. Several chemical transformations of the synthesized adamantyloxazolidin-2-ones were studied, including acidic hydrolysis accompanied by ring opening to form aminotriols, as well as the reactions of N-aminooxazolidinones with aromatic aldehydes and acid chlorides, leading to the corresponding hydrazones and acyl derivatives.