title: Diels-Alder reactions of five-membered heterocycles containing one heteroatom.
abstract: Diels-Alder reactions of five-membered heterocycles containing one heteroatom with anN-arylmaleimide were studied. Cycloaddition of 2,5-dimethylfuran (4) with 2-(4-methylphenyl)maleimide (3) in toluene at 60 °C gave bicyclic adduct5. Cycloadditions of3with 2,5-dimethylthiophene (11) and 1,2,5-trimethylpyrrole (14) were also studied. Interestingly, the bicyclic compound5cleanly rearranged, with loss of water, when treated withp-toluenesulfonic acid in toluene at 80 °C to give 4,7-dimethyl-2-p-tolylisoindoline-1,3-dione (6).
authors.affiliation: Department of Chemistry, Microbiotix, Inc., One Innovation Drive, Worcester, MA 01605 USA.
authors.forename: Xiaoyuan
authors.initials: X
authors.lastname: Ding
authors.affiliation: Department of Chemistry, Microbiotix, Inc., One Innovation Drive, Worcester, MA 01605 USA.
authors.forename: Son T
authors.initials: ST
authors.lastname: Nguyen
authors.affiliation: Department of Chemistry, Microbiotix, Inc., One Innovation Drive, Worcester, MA 01605 USA.
authors.forename: John D
authors.initials: JD
authors.lastname: Williams
authors.affiliation: Department of Chemistry, Microbiotix, Inc., One Innovation Drive, Worcester, MA 01605 USA.
authors.forename: Norton P
authors.initials: NP
authors.lastname: Peet
keywords: Diels-Alder reactions; acid-catalyzed reactions; dienes; dienophiles
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