Rhodium-Catalyzed One-pot Chemoselective Insertion-Rearrangement-Cyclization of Azavinyl Carbenes with 2‑Aminobenzyl Alcohols

Chemoselective insertion of in situ generated α-imino
rhodium
carbene onto the O–H bond of 2-aminobenzyl alcohols over the
N–H bond followed by [1,3]-alky shift has been successfully
accomplished for the synthesis of amine tethered ketone derivatives.
The resultant product was further cyclized under acidic conditions
to afford biologically important 3-aminoquinolines. Successful integration
of chemoselective insertion-cum-rearrangement and
cyclization in one pot offered access to various 3-aminoquinolines
in a good yield. Conversion of 3-aminoquinolines into biological important
motifs has also been demonstrated.