Synthesis of Adamantane Derivatives. 54. Synthesis of Novel 4-Azahomoadamantano-Fused Heterocycles via Hydrocyanation of 4-Azahomoadamant-3-ene

Article abstract of DOI:10.1021/jo00335a030

Photolysis of 1-azidoadamantane (1) in an aqueous NaCN-n-hexane two-phase system with Adogen 464 as a phase-transfer catalyst gave 3-cyano-4-azahomoadamantane (3), a hydrocyanation product of 4-azahomoadamant-3-ene (2).AlCl3-catalyzed decomposition of 1 in the presence of trimethylsilyl cyanide also afforded 3. 3 gave the corresponding amino acid 6 and its ester 7. 4-Azahomoadamantano<3,4>-fused hydantoin, iminohydantoin, iminothiohydantoin, and thiohydantoin, 12-17, were readily prepared by the reactions of 3 with appropriate isocyanates and isothiocyanates.The reactions of 3 with dimethyl acetylenedicarboxylate, methyl vinyl ketone, and diketene afforded the corresponding iminopyrroline (20), aminopyrroline (23), and aminopyrrolinone (26).Acetylation of 3 gave N-acetylamino derivative 27, which was converted to Δ²-oxazolinium perchlorate 30 via N-acetylamino acid 29.