A nucleophilic 1,3-rearrangement leading to 3,4-disubstituted 3,4-dihydroquinolines

A new nucleophilic 1,3-rearrangement is observed when treating 2-methoxyquinolino-3-lithium with an α-C substituted deoxybenzoin, and this rearrangement yielded an unusual 3,4-disubstituted 3,4-dihydroquinoline. Several similar reactions were designed and executed to investigate this novel 1,3-rearrangement, and a mechanism involving a nucleophilic addition and a following 1,3-rearrangement with an unusual dearomatization on the quinoline ring is proposed.

A novel nucleophilic 1,3-rearrangement is observed when treating 2-methoxyquinolino-3-lithium with α-C substituted deoxybenzoins, and the reaction mechanism is discussed.Figure optionsDownload as PowerPoint slide