Engaging Morita-Baylis-Hillman Reaction for the Generation of Isobenzofuran and the Consequent Entry into Highly Substituted Aromatic Systems

Abstract

The hemiacetal resulting from the Morita-Baylis-Hillman (M-B-H) reaction of o-phthalaldehyde is shown to be an excellent precursor for the synthesis of polycyclic aromatic hydrocarbons. The former on acid-catalyzed dehydration generates an isobenzofuran intermediate, which in turn is trapped with various electron-deficient dienophiles leading to a facile synthesis of functionalized aromatic systems.

Key words

carbocycles - cycloadditions - Diels-Alder reactions - naphthalenes - acrylates

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