Facile C-N cleavage in a series of bridged lactams.
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.
Lei
Yao
Y
Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Room 4070, Malott Hall, University of Kansas, Lawrence, KS 66045-7582, USA.
Wrobleski
Aaron D
AD
Golden
Jennifer E
JE
Powell
Douglas R
DR
Aubé
Jeffrey
J
D000577:Amides / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation
D000577:Amides; D007769:Lactams