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Synlett 2011(9): 1293-1295
DOI: 10.1055/s-0030-1260556
DOI: 10.1055/s-0030-1260556
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Efficient Synthesis of Substituted Polyarylphthalimides via Cycloaddition of Cyclopentadienones with 2-Bromomaleimide
Further Information
Received
16 December 2010
Publication Date:
05 May 2011 (online)
Publication History
Publication Date:
05 May 2011 (online)
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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
- Supporting Information for this article is available online:
- Supporting Information
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References and Notes
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.