Regioselectivity of the Mannich Reaction on Pyrrolo[2,3-d]pyrimidine Nucleosides Related to 7-Deaza-2'-deoxyadenosine or 7-Deaza-2'-deoxyguanosine

Frank Seela; Yaoming Chen; Matthias Zulauf

doi:10.1055/s-1997-1305

Synthesis 1997; 1997(9): 1067-1072
DOI: 10.1055/s-1997-1305

paper

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Regioselectivity of the Mannich Reaction on Pyrrolo[2,3-d]pyrimidine Nucleosides Related to 7-Deaza-2'-deoxyadenosine or 7-Deaza-2'-deoxyguanosine

Frank Seela^*

^*Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany, Fax +49(541)9692370; E-mail: Fraseela@rz.Uni-Osnabrueck.DE

Abstract

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Mannich reactions were performed on 7-deazapurine 2'-deoxyribonucleosides and the regioselectivity was studied. 7-Deaza-2'-dioxyadenosine (2'-deoxytubercidin, 4a) furnished the 7-substituted Mannich base 5a. The side chain was introduced in the 8-position when 7-deaza-2'-deoxyguanosine was used (Mannich base 7a). The regioselectivity changed back from position 8 to 7 when the reaction was performed on 4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine 2'-deoxyribonucleoside (12). Thus a 7-substituted Mannich product of 7-deaza-2'-deoxyguanosine could be obtained after demethylation and oxidation of the methylthio group followed by displacement of the oxidized 2-substituent with ammonia.

nucleosides

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