Studies on the adamantylation of N-heterocycles and nucleosides

Adamantylation of several N-heterocycles and of two ribonucleosides (uridin e and toyocamycin) was studied. The exact substitution position by the adam antyl carbocation generated tram adamantan-1-ol in CF3COOH depends on the n ature of the heterocyclic substrate. Thus, adamantylation of an additional exocyclic amino group (see Scheme 1), N-adamantylation of the heterocycle ( Scheme 2), C-adamantylation of the heterocycle (Scheme 3), as well as the f ormation of heterocyclic N-adamantylcarboxamides via the Ritter reaction (S cheme 4) are possible. The structures of the reaction products were determi ned by means of elemental analysis and NMR, UV,and IR spectroscopy.