18066-77-8Relevant articles and documents
Bronsted acid assisted activation of imide carbonyl group: Regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine
Selvakumar, Jayaraman,Ramanathan, Chinnasamy Ramaraj
supporting information; experimental part, p. 7643 - 7646 (2011/12/03)
Activation of imide carbonyl group with trifluoromethanesulfonic acid facilitates the intramolecular cyclization of phenethylphthalimides to give a fused isoindoloisoquinolinone skeleton. The first one pot regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine has been successfully executed using this methodology.
Regioselective Heck reaction of N-vinylphthalimide: A general strategy for the synthesis of (E)-N-styrylphthalimides and phenethylamines
Alacid, Emilio,Najera, Carmen
experimental part, p. 1316 - 1322 (2009/05/30)
The arylation of N-vinylphthalimide takes place at the β-position with aryl iodides, bromides and chlorides using palladium acetate [Pd(OAc) 2] or phenone oxime-derived palladacycles as catalysts under phosphine-free conditions. The reaction is succesfully carried out in organic solvents, such as DMF, in the presence of an organic base, such as dicyclohexylmethylamine, and with TBAB as additive at 120°C under conventional or microwave heating. (E)-N-Styrylphthalimides are mainly obtained using a rather low palladium loading (0.05-1 mol%). Similar catalytic efficiency is observed using a Kaiser oxime resin-derived palladacycle, which allows reuse of the polymeric complex for three cycles. The high regioselectivity observed supports that these palladacycles work as a source of Pd(0)spec ies operating mainly through a neutral mechanism. The syntheses of 2-thienylphenethylamine and mescaline have been performed by subsequent hydrogenation with Wilkinson's catalyst and hydrazinolysis.
