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Synlett
DOI: 10.1055/a-2560-8133
DOI: 10.1055/a-2560-8133
letter
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
We thank the National Natural Science Foundation of China (Grant No. 21871087), the Open Research Fund of Key Laboratory of Polar Materials and Devices, Ministry of Education for financial support.
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 synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2560-8133.
- Supporting Information
Publication History
Received: 12 December 2024
Accepted after revision: 17 March 2025
Accepted Manuscript online:
17 March 2025
Article published online:
11 April 2025
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