Base-Induced Annulation of Glycal-Derived -iodopyranone with 2-Aminopyrimidinones: Access to Chiral Imidazopyrimidinones

A simple, environmentally benign and catalyst-free method for the synthesis of chirally enriched imidazo[1,2-a]pyrimidinone glycohybrids has been successfully developed. The protocol is based on a base-induced annulation of alpha-iodo-pyranone with Michael addition of 2-aminopyrimidinones followed by intramolecular nucleophilic substitution reaction. The privilege of this method includes mild reaction conditions, eco-friendly solvent and a transition-metal-free approach. Moreover, using straightforward simple methods, this reaction method exhibits a broad range of substrate scope and remarkable tolerance toward various functional groups. A mild synthetic protocol was developed to synthesize novel imidazo[1,2-a]pyrimidinone-based glycohybrids in good to excellent yields. The synthetic method involves a base-induced Michael-type addition reaction using various 2-aminopyridinones and sugar-derived iodopyranones, followed by intramolecular nucleophilic substitution. image