Gold‐Catalyzed Annulation of Ynamides with Aminocarbonyls as a Route to 2‐Aminoquinolines Diversely Substituted at the 4th‐Position

Abstract

AbstractGold‐catalyzed interplay between ynamides and aminocarbonyls comprises a route to 2‐aminoquinolines. This modular annulation proceeds under relatively mild conditions (Ph3PAuCl/AgNTf2 5 mol %, DCE, 60–80 °C), and a number of functionalities were compatible (42 examples; 25–98% yields). In contrast to a group of other gold‐catalyzed methods employing the ynamide/amine combinations for the assembly of 2‐aminoquinolines, the developed approach utilizes a diversity of aminocarbonyl substrates and, in particular, allows a variation of the substituents in the 4th quinoline position. The synthetic potential of the obtained heterocyclic products was illustrated by post‐modifications of the quinoline backbone and the peripheral substituents.