Collect. Czech. Chem. Commun. 2011, 76, 1043-1054
Published online 2011-07-21 11:52:50

Synthesis of 7-substituted 3-β-D-ribofuranosyl-3H-imidazo[2,1-i]purines

Tuomas Karskela*, Karel D. Klika and Harri Lönnberg

Department of Chemistry, University of Turku, Vatselankatu 2, FIN-20014 Turku, Finland


A method for the synthesis of 7-substituted 3-β-D-ribofuranosyl-3H-imidazo[2,1-i]purines has been devised whereby compounds were prepared in a few steps from a common intermediate, 3-(2′,3′-O-isopropylidene-β-D-ribofuranosyl)-3H-imidazo[2,1-i]purine-7-carbaldehyde, obtained from the reaction of 2′,3′-O-isopropylideneadenosine with bromomalonaldehyde. The formyl group of the carbaldehyde was subsequently reductively aminated and the resulting secondary amines were then further derivatized either by acylation, lactamization or reductive alkylation.

Keywords: Nucleosides; Heterocycles; Purine bases; NMR spectroscopy.

References: 41 live references.