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

Abstract

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.

Key words

arenes - cyclopentadienones - Diels-Alder reaction - elimination - imides

References and Notes

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12

Succinimide has also been evidenced in the reaction mixture and thus aromatization may be attributed, at least partly, to a hydrogen transfer from the dihydro intermediate to maleimide.