A combination of polarity reversal, Diels–Alder cycloaddition and skeletal remodeling to access pyridine-fused nitrones

Abstract

An unprecedented cascade strategy consisting of polarity reversal, normal electron-demand Diels–Alder cycloaddition and skeletal remodeling was developed to construct novel pyridine-fused nitrones in up to 82% yield. The key to the success was the umpolung process, which transformed the electron-deficient 3-nitropyridinium ring into a reactive, π-extended cyclic nitroalkene, serving as a rarely reported hetero-diene to participate in normal Diels–Alder cycloadditions.