The synthesis of certain ribofuranosylindazoles

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Abstract
The synthesis of 1‐(β‐D‐ribofuranosyl)indazole (4), 2‐(β‐D‐ribofuranosyl)indazole (5) and 6‐, 5‐, and 4‐nitro‐2‐(β‐D‐ribofuranosyl)indazole (8a, 8b, and 8c, respectively), has been accomplished in good yield by the condensation of the appropriate N‐trimethylsilylindazole (1, 6a, 6b, and 6c) with 2,3,5‐tri‐O‐acetyl‐D ‐ribofuranosyl bromide (2) followed by subsequent deacetylation of the reaction products. The site of ribosylation and the assignment of anomeric configuration for all nucleosides reported is discussed. This has furnished the first indazole nucleosides with assigned anomeric configurations and the site of ribosylation has been established on the basis of uv comparisons with model methyl compounds.