Synthesis of Polysubstituted Fused Pyrroles by Gold-Catalyzed Cycloisomerization/1,2-Sulfonyl Migration of Yndiamides
Philip Cameron‐Smith, Yubo Jiang, Zixuan Tong, Helena D. Pickford, Kirsten E. Christensen, Jeremy Nugent, Edward A. Anderson
Abstract
Yndiamides (bis-N-substituted alkynes) are valuable precursors to azacycles. Here we report a cycloisomerization/1,2-sulfonyl migration of alkynyl-yndiamides to form tetrahydropyrrolopyrroles, unprecedented heterocyclic scaffolds that are relevant to medicinal chemistry. This functional group tolerant transformation can be achieved using Au(I) catalysis that proceeds at ambient temperature, and a thermally promoted process. The utility of the products is demonstrated by a range of reactions to functionalize the fused pyrrole core.
Topics & Concepts
CycloisomerizationChemistrySulfonylCatalysisCombinatorial chemistryPyrroleOrganic chemistryAlkylCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsSynthesis and Characterization of Pyrroles