Preparation and Diels–Alder reactions of 1′-heterosubsituted vinylimidazoles. Issue 23 (3rd June 2015)

• Record Type: Journal Article
• Authors: Ray, Abhisek; Mukherjee, Sabuj; Das, Jayanta; Bhandari, Manoj K.; Du, Hongwang; Yousufuddin, Muhammed; Lovely, Carl J.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 23(2015)
• Page Start: 3518
• Page End: 3522
• Publication Date: 2015-06-03
• Subjects: Marine alkaloids -- Cycloaddition -- Stereoselective -- Hydroalumination -- Hydrosilylation -- Oxidation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.01.190
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: 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 4-vinylimidazoles containing substituents on the vinyl moiety via hydroalumination/electrophilic trapping or hydrosilylation is described. These derivatives undergo Diels–Alder reactions with N -phenylmaleimide to provide the tetrahydrobenzimidazole derivatives. The cycloadducts derived from halosubstituted systems can undergo elimination, leading to the corresponding dihydrobenzimidazole, whereas the silyl and stannyl derivatives provide the corresponding 4-substituted tetrahydrobenzimidazole.