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-<i>cum</i>-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.