Preparation of 1-aryl-substituted isoindoline derivatives by sequential Morita-Baylis-Hillman and intramolecular Diels-Alder reactions.
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.
Clary
Kristen Nicole
KN
Department of Chemistry, University of Calgary, Calgary, AB, CanadaT2N 1N4.
Parvez
Masood
M
Back
Thomas George
TG
D018360:Crystallography, X-Ray; D003500:Cyclization; D054833:Isoindoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D054833:Isoindoles