title: Facile C-N cleavage in a series of bridged lactams.
abstract: A series of strained bi- and tricyclic amides has been shown to be unusually sensitive to cleavage of the C-N bond adjacent to the amide moiety. This bond undergoes facile breaking when subjected to treatment with H2/Pd(OH)2, MeI, and DDQ. In each case, the reaction is highly regioselective and mainly results in breaking the C-N bond that deviates the farthest from its natural planar state. Preliminary experiments that bear on the mechanisms of these reactions are described.
authors.affiliation: Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Room 4070, Malott Hall, University of Kansas, Lawrence, KS 66045-7582, USA.
authors.forename: Yao
authors.initials: Y
authors.lastname: Lei
authors.forename: Aaron D
authors.initials: AD
authors.lastname: Wrobleski
authors.forename: Jennifer E
authors.initials: JE
authors.lastname: Golden
authors.forename: Douglas R
authors.initials: DR
authors.lastname: Powell
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Aubé
mesh_terms: D000577:Amides / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D000577:Amides; D007769:Lactams