Palladium-Mediated Coupling Reactions of an Aminosubstituted Heterocycle. Direct Synthesis of C-Nucleosides Related to Adenosine

Abstract

Abstract C-Nucleosides of the pyrazolo[1, 5-a]-1, 3, 5-triazine aglycon system have been prepared by palladium-mediated coupling of 8-iodopyrazolo[1, 5-a]-1, 3, 5-triazines. 4-(N, N-Diisobutyloxycarbonyl)amino-8-iodopyrazolo[1, 5-a]-1, 3, 5-triazine and the furanoid glycal 1, 4-anhydro-2-deoxy-3-O[(1, 1 dimethylethyl)diphenylsilyl]-D-erythro-pent-1-enitol coupled in the presence of catalytic palladium(0) to yield, after desilylation of the intermediate silyl enol ether, a C-glycoside analog of adenosine.