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.