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A method for the synthesis of highly functionalized 4-aminoquinolines from sulphynamides and amides is presented. The amides are activated by triflic anhydride (Tf2O) and 2-chloropyridine (2-ClPy) and, as Movassaghi et al. have shown, can be used to prepare a wide range of heterocyclic structures. Sulphynamides can be prepared using copper catalysis and alkyl bromides and further derivatized by using Sonogashira chemistry. The main challenge in existing quinoline syntheses is the functionalization at the C-2 and C-3 positions. By combining the Sonogashira approach with the ynamide/amide methodology a wide range of substitutions at C-3 is possible and the C-2 and C-5 to C-8 positions are also accessible. In order to show the broad applicability of the methodology, it was found that the ynamides also readily react with paracyclophane-based amides, creating very interesting planar chiral compounds.