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Synthesis of Pyrano[2,3- b ]indol-4-ones Fused with Medium-Sized Rings: A Base-Induced C–C σ-Bond Insertion and Subsequent I 2 -Mediated 1,2-Acyl Migration/Cyclization Reaction

A novel tandem reaction starting from alkynones and cyclic ketones has been developed to efficiently synthesize pyranoindolones fused with a medium-sized ring. This process involves a base-induced C–C σ-bond cleavage… Click to show full abstract

A novel tandem reaction starting from alkynones and cyclic ketones has been developed to efficiently synthesize pyranoindolones fused with a medium-sized ring. This process involves a base-induced C–C σ-bond cleavage reaction of cyclic ketone and subsequent I 2 -mediated 1,2-acyl migration/cyclization reaction. Transition-metal-free and easily accessible starting materials make this 1,2-acyl migration/cyclization methodology attractive.

Keywords: reaction; fused medium; acyl migration; migration cyclization

Journal Title: Synlett
Year Published: 2024

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