Isatin derivatives are reactive electrophilic components for the Baylis–Hillman reaction

Abstract

Isatin derivatives readily react as the electrophilic component in the Baylis–Hillman reaction giving good to excellent yields of the respective adducts. It is generally accepted that ketones only take part in the Baylis–Hillman reaction under relatively extreme conditions, with a few exceptions. Isatin on the other hand readily reacts with acrylic acid derivatives in ethanol and or ethanol/THF mixtures in the presence of a catalytic quantity of DABCO. The solid state structures for these novel dioxindole derivatives were determined for two adducts by single-crystal X-ray diffraction spectroscopy, revealing an inside hydroxyl conformation.