Helvetica chimica acta

Studies on the Adamantylation of N??Heterocycles and Nucleosides

Z Kazimierczuk, A Orzeszko

Index: Kazimierczuk, Zygmunt; Orzeszko, Andrzej Helvetica Chimica Acta, 1999 , vol. 82, # 11 p. 2020 - 2027

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Citation Number: 14

Abstract

Abstract Adamantylation of several N-heterocycles and of two ribonucleosides (uridine and toyocamycin) was studied. The exact substitution position by the adamantyl carbocation generated from adamantan-1-ol in CF 3 COOH depends on the nature 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 ( ...