One-Pot synthesis of -alkylidene - Butyrolacton-2-ones (Tetronic Acid Derivatives): Polar solvent induces a new type of -lactonization

Article abstract of DOI:10.1055/s-0030-1258113

An efficient, one-pot synthetic protocol toward α-alkylidene γ- butyrolacton-2-ones, a rather unexplored class of heterocyclic scaffolds starting from primary amines, methyl acetoacetate, and chloroacetyl chloride is described. The mixture of MeCN-MeOH as a polar solvent triggers a new cycloaddition of the enaminone intermediate. The reaction is completed within 12 hours under reflux condition to produce the title compounds. Georg Thieme Verlag Stuttgart.