Synthesis of Novel N-carbohydrate-derived Heterocyclic Compounds by Nucleophilic Substitution Reaction of Carbohydrate Imidazole-1-sulfonates.

The nucleophilic substitution reaction of carbohydrate imidazole-1-sulfonates with pyrrole and other nitrogen heterocyclic compounds is reported for the first time. Several novel N-carbohydrate-derived heterocyclic compounds have been prepared by this displacement reaction. The desired carbon-nitrogen bond formation proceeds under mild conditions to generate the coupling products in good yields with readily available and inexpensive reagents. This method is particularly suitable for carbohydrate imidazole-1-sulfonates of primary alcohols. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the free supplemental file. [ABSTRACT FROM PUBLISHER]