New Route to 1-(5-Imidazolyl)ribofuranoid Glycals from Ribofuranosyl Chloride and 5-Lithio-imidazole.

Abstract

Reaction of ribofuranosyl chlorides with 2 eq of 5-lithio-imidazole afforded 1-(5-imidazolyl)ribofuranoid glycals in good yields. Hydrolysis of the glycal (3) with hydrochloric acid led to 4-(5-hydroxymethylfuran-2-yl)imidazole (7), which contains both hydrophilic and hydrophobic aromatic heterocycles.