title: Solvent-controlled bifurcated cascade process for the selective preparation of dihydrocarbazoles or dihydropyridoindoles.
abstract: A solvent-controlled cascade process has been identified for the dual purpose of the preparation of either dihydrocarbazoles or dihydropyridoindoles from identical N-aryl-α,β-unsaturated nitrones and electron-deficient allene starting materials. These reactions proceed smoothly under mild metal-free conditions affording a range of two types of skeletally distinct indole-based heterocycles in high yield and diastereoselectivity. These transformations demonstrate the use of a bifurcated cascade process that hinges on the ring-opening event of a benzazepine intermediate for the synthesis of skeletally diverse heterocyclic products and rapid access to biologically-significant, indole-based structures.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor St., Chicago, IL 60607 (USA).
authors.forename: Dong-Liang
authors.initials: DL
authors.lastname: Mo
authors.forename: Donald J
authors.initials: DJ
authors.lastname: Wink
authors.forename: Laura L
authors.initials: LL
authors.lastname: Anderson
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D002227:Carbazoles; D007211:Indoles; D009589:Nitrogen Oxides; D012997:Solvents; C015388:nitrones
keywords: Cascade reaction; dihydrocarbazole; dihydropyridoindole; nitrone; solvent effect