Nitrogen Atom Transfer Enables the (5+1) Annulation Reaction to Access Aminoisoquinolines

Abstract

Herein, a catalytic synthetic transformation offering a series of -NH 2 group-bearing aminoisoquinolines with moderate to good yields has been showcased. Interestingly, the nitrogen atom of the isoquinoline ring is coming from the reaction medium upon metal-assisted C�N bond cleavage. Moreover, this (5+1) annulation reaction shows broad substrate variation. Furthermore, the derivatization of the isoquinoline core via functional group interconversions and mechanistic studies to identify the reaction intermediate have been carried out successfully.

Twofold Heteroannulation Reactions Enabled by Gold(I)/Zinc(II) Catalysts: Synthesis of Amine-Substituted Diaryl[c,h][1,6]naphthyridines

“…Interestingly, 2-alkynylarylnitriles which could be accessed easily are suitable substrates for accessing various aryl-fused N -heterocycles . We have recently shown that such types of alkynes are excellent starting precursors to access aminoisoquinolines upon reaction with nitrile solvent . During this study, we realized that the C–C triple bond and −CN group could be activated by the metal catalyst toward the nucleophilic addition in a sequential manner.…”