An unusual rearrangement during diazotization of a 5-aminoimidazole nucleoside
Abstract
Treatment of methyl 5-amino-1,(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxylate with sodium nitrite in the presence of 11N nitric acid at –20 °C yielded methyl 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-oxo-Δ4-imidazoline-4-carboxylate.