Amine-Mediated Transimination and Aromatization-Triggered Domino Reaction in the Synthesis of Polyfunctionalized 4‑Aminoquinolines

Dearomatization
provides numerous possibilities for the development of new
transformative modes of aromatic compounds. A conceptually novel metal-free
multicomponent domino reaction of the dearomatized products of 2-alkynylanilines
is developed. The reaction involves the secondary amine-mediated transimination
with α-amino nitriles and subsequent aromatization-triggered
cascade rearrangement, nucleophilic cyclization, and retro-Strecker
reaction. This process provided a new practical method for the rapid
synthesis of polyfunctionalized 4-aminoquinolines from readily available
starting materials.