The multicomponent reactions of cyclic anhydrides as extended dipoles in the formation of polycyclic compounds are described. α-chloroketimines is found to react with homophthalic anhydride and cyclize to form complex polycyclic lactones. Aromatic aldehydes and ketones are demonstrated to react with homophthalic anhydrides under Lewis acid or base-mediated conditions. the thermal reaction between homophthalic anhydrides and carbon-carbon multiple bonds and a base-mediated variant that id consistently higher yielding is reported. Homophthalic anhydride is found to undergoe an interesting annulation reaction with ortho-cyanobenzyl bromides in the presence of triethylamine. The cycloaddition reaction takes place through a [4 + 2]-cycloaddition between the enolate generated from homophthalic anhydride (diene) and the highly reactive chloroquinone 277 as the dienophile counterpart, followed by extrusion of carbon dioxide and hydrogen chloride.
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