Abstract

Pyrolysis of the neat hydrochloride salts of imidazolyl-tetritols 6, 8, and 9 led to the 4-glycofuranosyl-1H-imidazole anomer mixtures 2/3, 4/5, and ent-4/ent-5, respectively. The same pairs of C-nucleosides were also obtained in one-pot procedures by microwave irradiation of mixtures containing formamidine acetate (=formimidamide acetic acid salt), a few drops of H2O, and the appropriate hexose or hexulose, i.e., D-fructose (or D-glucose), D-galactose, and L-sorbose, respectively. Microwave irradiation clearly brought about sequential double condensation of formamidine with hexoses or hexuloses and acid-catalyzed intramolecular cyclization of the intermediate linear imidazolyl-tetritols.

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