Stereoisomeric N-(p-nitrobenzoyl)-5-aminomethylbicyclo[2.2.1]hept-2-enes.: Synthesis, epoxidation, 1H and 13C NMR spectra

Preparation is described of stereoisomeric (p-nitrobenzoyl)-5-aminomethylbicyclo[2.2.1]hept-2-enes and their epoxidation by peracetic acid. A possibility of selective reduction of separated fragments in the polyfunctional compound using sulfur in alkaline medium, hydrazine hydrate in the presence of a nickel catalyst, and lithium aluminum hydride was demonstrated by an example of one of amides. By reaction with electrophilic reagents from the amines synthesized, (p-aminobenzoyl)endo-5-aminomethylbicyclo[2.2.1]hept-2-ene and (p-aminobenzoyl)-endo-2-aminomethylbicyclo[2.2.1]hept-2-ene, new bicyclic compounds containing alongside the amide group also sulfonamide, carboxamide, urea, and thiourea moieties were obtained. The structure of compounds obtained was confirmed by H-1 and C-13 NMR spectroscopy, by two-dimensional spectra measured along COSY and NOESY procedures.