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

• DOI: 10.1021/acs.orglett.6b02643
• Publication Date: 2016-10-05T14:37:19Z
• Authors: Runzhe Song; Zhaomeng Han; Qiuqin He; Renhua Fan
• Keywords: Aromatization; Aminoquinolines; Cascade reaction; Domino

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