The basic ionic liquid 1-ethyl-3-methylimidazolium acetate ([C2C1Im][OAc]) could efficiently catalyze the conversion of 2-amino-2-deoxy-d-glucose (GlcNH2) into deoxyfructosazine (DOF) and fructosazine (FZ). Mechanistic investigation by NMR studies disclosed that [C2C1Im][OAc], exhibiting strong hydrogen bonding basicity, could coordinate with the hydroxyl and amino groups of GlcNH2via the promotion of hydrogen bonding in bifunctional activation of substrates and further catalyzing product formation, based on which a plausible reaction pathway involved in this homogeneous base-catalyzed reaction was proposed. Hydrogen bonding as an activation force, therefore, is responsible for the remarkable selectivity and rate enhancement observed.

An efficient one-pot dehydration process for convert D-glucosamine hydrochloride (GlcNH 2 ) into 2-(D-arabino-1 0 ,2 0 ,3 0 ,4 0 -tetrahydroxybutyl)-5-(D-erythro-2 00 ,3 00 ,4 00 -trihydroxybutyl)pyrazine (deoxyfructosazine, DOF) and 2,5-bis-(D-arabino-1,2,3,4-tetrahydroxybutyl)pyrazine (fructosazine, FZ) was reported. A taskspecific basic ionic liquid, 1-butyl-3-methylimidazolium hydroxide ([BMIM]OH), was employed as an environmentally-friendly solvent and catalyst. The products were qualitatively and quantitatively characterized by MALDI-TOF-MS, 1 H NMR and 13 C NMR spectroscopy. The influences of GlcNH 2 concentrations, reaction temperature, reaction time, additives and co-solvents on the yields of products were studied. The maximum yield of 49% was obtained in the presence of [BMIM]OH and DMSO under optimized conditions (120 C, 180 min). In addition, a plausible mechanism was proposed. Our project was to develop efficient, atom economical and eco-compatible routes for the synthesis of heterocyclic compounds from marine biomass (or nitrogen-containing biomass). The obtained aromatic heterocyclic compounds showed potential pharmacological action and physiological effects, and they also could be utilized as flavoring agents in the food industry.

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