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Synthesis 2004(12): 2026-2034  
DOI: 10.1055/s-2004-829174
PAPER
© Georg Thieme Verlag Stuttgart · New York

Regioselective Functionalization of Guanine: Simple and Practical Synthesis of 7- and 9-Alkylated Guanines Starting from Guanosine

Genadiy Kalayanova,b, Suzana Jakšaa, Tommaso Scarciac, Jože Kobe*a
a National Institute of Chemistry, Hajdrihova 19, 1115 Ljubljana, Slovenia
Fax: +386(61)14760300; e-Mail: joze.kobe@ki.si;
b Present Address: Medivir AB, Lunastigen 7, 141 44 Huddinge, Sweden
c University of Bari, via E. Orabona 4, 70125 Bari, Italy
e-Mail: scarcia@farmchim.uniba.it;
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Publikationsverlauf

Received 24 November 2003
Publikationsdatum:
27. Juli 2004 (online)

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Abstract

Reaction of N 2-acetyl-9- and/or -7-benzylated guanines 8 and 12 with selected alkylating agents in 1-methyl-2-pyrrolidone at 120 °C yielded the guaninium salts 9 and 13. The salts were consequently transformed by phase transfer hydrogenation into N7- and N9-isomers 10 and 14, respectively, in a highly regioselective manner. A convenient deoxygenation of both derivatives, achieved via the corresponding O 6-arenesulfonates, into 2-aminopurine potential prodrugs was also established.

Key words

N 2-acetyl-7- and 9-benzylguanine - benzylation - alkyl­ations - hydrogenations - regioselectivity