Gold-Catalyzed Spirocyclization of Furan-ynones and Unexpected Skeleton Rearrangement of the Resulting Spirohydrofurans
Yulong Chen, Wei Xu, Xin Xie, Miaomiao Pei, Mingduo Lu, Yaotong Wang, Yuanhong Liu
Abstract
A gold-catalyzed cyclization of aniline-tethered furan-ynones has been developed. The reaction proceeds via trapping of the resulting stabilized cationic intermediate with an amide group leading to polycycles featured with a spiro-cyclohexadienone-hydrofuran framework with high efficiency. The resulting N-alkyl products undergo photorearrangements to afford the ring-enlarged benzo[b]azepine derivatives or iron-promoted novel rearrangement to diketone-containing spirocycles involving multiple C–X bond cleavages and formations.
Topics & Concepts
ChemistryFuranAzepineAnilineAmideRing (chemistry)Medicinal chemistryCatalysisAlkylCationic polymerizationOrganic chemistryCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods