Synthesis of Pyrano[2,3-b]indol-4-ones Fused with Medium-Sized Rings: A Base-Induced C–C σ-Bond Insertion and Subsequent I₂-Mediated 1,2-Acyl Migration/Cyclization Reaction

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 I₂-mediated 1,2-acyl migration/cyclization reaction. Transition-metal-free and easily accessible starting materials make this 1,2-acyl migration/cyclization methodology attractive.

Key words

C–C σ-bond cleavage - 1,2-acyl migration/cyclization - transition-metal-free - mild reaction conditions - one-pot synthesis

Publikationsverlauf

Eingereicht: 12. Dezember 2024

Angenommen nach Revision: 17. März 2025

Accepted Manuscript online:
17. März 2025

Artikel online veröffentlicht:
11. April 2025

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