title: Preparation of 1-aryl-substituted isoindoline derivatives by sequential Morita-Baylis-Hillman and intramolecular Diels-Alder reactions.
abstract: Aldimines underwent Morita-Baylis-Hillman reactions with dienes activated by sulfonyl or nitrile groups. The N-allyl or propargyl derivatives of the products were subjected to intramolecular Diels-Alder cycloadditions to produce the corresponding partly saturated 1-arylisoindoline derivatives. The cycloadducts in the nitrile-activated N-propargyl series were aromatized by base-mediated elimination of HCN to afford 1-arylisoindolines, which were in turn oxidized to the corresponding 3-arylisoindolin-1-ones.
authors.affiliation: Department of Chemistry, University of Calgary, Calgary, AB, CanadaT2N 1N4.
authors.forename: Kristen Nicole
authors.initials: KN
authors.lastname: Clary
authors.forename: Masood
authors.initials: M
authors.lastname: Parvez
authors.forename: Thomas George
authors.initials: TG
authors.lastname: Back
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D054833:Isoindoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D054833:Isoindoles