title: Heterogeneous Cu(II) -catalysed solvent-controlled selective N-arylation of cyclic amides and amines with bromo-iodoarenes.
abstract: A selective N-arylation of cyclic amides and amines in DMF and water, respectively, catalysed by Cu(II) /Al2 O3 has been achieved. This protocol has been employed for the synthesis of a library of arenes bearing a cyclic amide and an amine moiety at two ends, including a few scaffolds of therapeutic importance. The mechanism has been established based on detailed electron paramagnetic resonance (EPR) spectroscopy, X-ray photoelectron spectroscopy (XPS), UV diffuse reflectance spectroscopy (DRS) and inductively coupled plasma-mass spectrometry (ICP-MS) studies of the catalyst at different stages of the reaction. The Cu(II) /Al2 O3 catalyst was recovered and recycled for subsequent reactions.
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata-700032 (India), Fax: (+91) 33-24732805.
authors.forename: Debasish
authors.initials: D
authors.lastname: Kundu
authors.forename: Sukalyan
authors.initials: S
authors.lastname: Bhadra
authors.forename: Nirmalya
authors.initials: N
authors.lastname: Mukherjee
authors.forename: Bojja
authors.initials: B
authors.lastname: Sreedhar
authors.forename: Brindaban C
authors.initials: BC
authors.lastname: Ranu
mesh_terms: D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004578:Electron Spin Resonance Spectroscopy; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D056951:Photoelectron Spectroscopy; D012997:Solvents / Q000737:chemistry*
chemical_list: D000577:Amides; D000588:Amines; D006846:Hydrocarbons, Halogenated; D012997:Solvents; D003300:Copper
keywords: amides; amines; bioactive scaffolds; heterogeneous catalysis; solvent-controlled selectivity