Adamantyl-substituted amino alcohols. Synthesis and functionalization at the nitrogen and oxygen nucleophilic centers

1-Aminoadamantanes and 1-aminomethyladamantanes were brought into reactions with p-nitrophenyloxirane and 9-carbazolylmethyloxirane. The reactions occurred in a regioselective fashion according to the Krasusky rule, which was confirmed by the H-1 and C-13 NMR data. The resulting amino alcohols having a p-nitrophenyl moiety were subjected to functionalization at the nitrogen and oxygen nucleophilic centers using p-nitrobenzenesulfonyl chloride, p-nitrobenzoyl chloride, and hexamethyldisilazane, and N,O-bisacyl derivative was synthesized. The structure of the products was proved by IR and H-1 NMR spectroscopy.