Abstract:
Metal catalyzed post-Ugi cyclization of bis-amides
is reported in this study. Exposure of bis-amides to Pd(II) catalyst
triggered the formation of seven-membered benzoxazepinones.
This investigation established that changing the catalyst to a
Echavarren’s gold(I) turned off cyclization to seven member ring
and turned on 6-exo-dig annulations to afford family of sixmembered benzoxazinones. To support the proposed mechanisms, quantum chemical based density functional theory
calculations have been performed and validated. This novel
method obtained molecular complexity up to four modular inputs
and divergence of two different skeletons. 2D NMR spectroscopic
techniques and single crystal X-ray diffraction established the
proposed structures.
