Reactions of p-Nitrophenyloxirane with Amines Containing Fragments with Bicyclic Skeleton

Reactions of p-nitrophenyloxirane with amines containing fragments with bicyclic skeleton of norbornene, norbornane, epoxynorbornane (stereoisomeric exo- and endo-5-aminomethylbicyclo2.2.1]hept-2-enes, N-benzyl-endo-5-aminomethylbicyclo2.2.1]hept-2-ene, endo-5-(2-aminoethyl)bicyclo2.2.1]hept-2-ene, stereoisomeric exo- and endo-2-aminomethylbicyclo2.2.1]heptanes, 2-(1-aminoethyl)bicyclo2.2.1]heptane, exo-5-aminomethyl-exo-2,3-epoxybicyclo2.2.1]heptane) were investigated. The aminolysis of p-nitrophenyloxirane occurred regioselectively according to Krasusky rule as was proved by ¹H and ¹³C NMR data. As shown by ¹H and ¹³C NMR spectroscopy the oxyalkylation product obtained from N-benzyl-endo-5-aminomethylbicyclo2.2.1]hept-2-ene was composed of two diastereomers originating from the presence of a chiral nitrogen atom in the rear part of the rigid bicyclic skeleton. New products of amino groups transformation in the molecules of hydroxyamines were obtained by reaction with p-methylbenzoyl chloride and p-nitrophenylsulfonyl chloride. Regioselectivity of the attack of electrophilic reagents on the nitrogen in the hydroxyamines was confirmed by IR and ¹H NMR spectra of the products. The data on pharmacological activity tests of N-2-hydroxyethyl(p-nitrophenyl)-5-aminomethylbicyclo2.2.1]hept-2-ene are reported.