Gold(I)-Catalyzed Heteroannulation of Salicylic Amides with Alkynes: Synthesis of 1,3-Benzoxazin-4-one Derivatives
Masahiro Abe, Megumu Kawamoto, Mayu Inoue, Tetsutaro Kimachi, Kiyofumi Inamoto
Abstract
Gold(I)-catalyzed heteroannulation affords the efficient and straightforward construction of heterocyclic compounds. Herein, we developed a gold(I)-catalyzed heteroannulation of salicylic amides with alkynes producing a broad range of 1,3-benzoxazin-4-ones. The utility of this protocol was highlighted by synthesizing variously substituted benzoxazinones containing quaternary carbon centers, showing a high functional group tolerance and excellent atom economy of the thus introduced reaction course.
Topics & Concepts
ChemistryCatalysisCombinatorial chemistryFunctional groupReaction conditionsQuaternary carbonAtom economyOrganic chemistryEnantioselective synthesisPolymerCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms