Carboxamides and amines having two and three adamantane fragments

New carboxamides having two and three adamantane fragments were synthesized from adamantanecarboxylic acid chlorides and adamantane-containing amines. The amides were reduced to the corresponding amines, and the latter were converted into N-p-nitrophenylsulfonyl and N-p-tolylsulfonylcarbamoyl derivatives by treatment with p-nitrobenzenesulfonyl chloride and p-toluenesulfonyl isocyanate, respectively. The structure of the newly synthesized compounds was confirmed by IR and 1H NMR spectroscopy. Some carboxamides turned out to be inactive in the reduction with lithium tetrahydridoaluminate, which was discussed in terms of the results of semiempirical quantum-chemical calculations.