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

Gold-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 & DEG;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 4(th) quinoline position. The synthetic potential of the obtained heterocyclic products was illustrated by post-modifications of the quinoline backbone and the peripheral substituents.

Automated summary

The gold-catalyzed interplay between ynamides and aminocarbonyls provides a pathway to 2-aminoquinolines. This modular annulation reaction occurs under mild conditions and is compatible with various functionalities. Unlike other gold-catalyzed methods, this approach allows for the use of diverse aminocarbonyl substrates and allows for the variation of substituents in the 4th position of the quinoline. The obtained heterocyclic products demonstrate synthetic potential through post-modifications of the quinoline backbone and peripheral substituents.