Gold(I)‐Catalyzed Annulation of Pyridines Containing Alkyne: Synthesis of N ‐Alkenyl Pyridonyl Azides via Rearrangement

Abstract

ABSTRACT A novel strategy, involving the preparation of gold‐catalyzed cyclization salts and the rearrangement of these salts in the presence of azides, has been developed for the synthesis of N ‐alkenyl pyridonyl azides. The method was proven to tolerate a large number of groups and to produce moderate to excellent yields of transformation in reactions involving chains of different lengths. The usage of powerful electron‐withdrawing groups, such as the nitro group, determined the method's limitations. The five‐membered ring was shown to be easier to create in the first stage when rings of various sizes were formed with trifluoromethyl groups, whereas the six‐membered ring was more reactive in the second stage.