Abstract
Abstract4-Isocyanobut-1-ene reacted rapidly with acetyl bromide to afford an unstable imidoyl bromide adduct. Subsequent in situ cyclization under Heck conditions generated a stable prototropic isomer of 2-acetyl-3-methylpyrrole. The reactivity of this molecule toward acids, bases, and oxidants was explored, and its conversion into an α-methylidene γ-lactam was demonstrated. In protonated form, the molecule functioned as a reactive dienophile in Diels–Alder reactions.
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