Synthesis of pyranobenzopyrans from D-glucal using ionic liquids.

Imidazolium room temperature ionic liquids (RTILs) were used as solvents in the Lewis acid-catalyzed cycloaddition reactions of D-glucal with substituted salicylaldehydes. These reactions selectively led to various, novel, cis-pyrano [4,3-b]benzopyrans in modest yields, different products than those isolated from analogous solution studies. Furan diol was isolated as the major byproduct from all the reactions. The use of RTILs facilitated the use of unprotected sugars in these reactions.