Efficient Synthesis of Substituted Polyarylphthalimides via Cycloaddition of Cyclopentadienones with 2-Bromomaleimide

Functionalized tetraarylphthalimides or diarylphthalimides fused with an acenaphthene moiety have been prepared in one step from 2-bromomaleimide and tetraarylcyclopentadienones (tetracyclones) or 7,9-diaryl-8H-cyclopentacenaphthylene-8-ones (acecyclones). The reaction, involving a cycloaddition―decarbonylation―dehydrobromination sequence, gives high isolated yields and is compatible with the presence of various functional groups.