title: Preparation and Diels-Alder reactions of 1'-heterosubsituted vinylimidazoles.
abstract: A Diels-Alder/rearrangement sequence has been pursued in our lab en route to a number of oroidin dimers. In order to access the fully substituted core of these molecules, 1',2'-disubstituted 4-vinylimidazoles were required as dienes. The preparation of a series of a 4-vinylimidazoles containing substituents on the vinyl moiety via hydroalumination/electrophilic trapping or hydrosilylation are described. These derivatives undergo Diels-Alder reactions withN-phenylmaleimide to provide the tetrahydrobenzimidazole derivatives. The cycloadducts derived from halosubstituted systems generally undergo elimination, leading to the corresponding dihydrobenzimidazole, whereas the silyl and stannyl derivatives provide the corresponding 4-substituted tetrahydrobenzimidazole.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019-0065, USA.
authors.forename: Abhisek
authors.initials: A
authors.lastname: Ray
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019-0065, USA.
authors.forename: Sabuj
authors.initials: S
authors.lastname: Mukherjee
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019-0065, USA.
authors.forename: Jayanta
authors.initials: J
authors.lastname: Das
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019-0065, USA.
authors.forename: Manoj K
authors.initials: MK
authors.lastname: Bhandari
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019-0065, USA.
authors.forename: Hongwang
authors.initials: H
authors.lastname: Du
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019-0065, USA.
authors.forename: Muhammed
authors.initials: M
authors.lastname: Yousufuddin
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019-0065, USA.
authors.forename: Carl J
authors.initials: CJ
authors.lastname: Lovely