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Synthesis 2025; 57(02): 425-440
DOI: 10.1055/a-2382-9631
DOI: 10.1055/a-2382-9631
paper
Special Topic Dedicated to Prof. H. Ila
PIFA-Mediated Intramolecular Dearomatization of Phenol-Tethered 1,2-Diazoles: Synthesis of Spirocyclohexadienone-pyrazolo[3,4-b]piperidinones
This work was supported by the Department of Atomic Energy, Government of India.
Abstract
In recent years, the significance of spirocyclic motifs in drug discovery has increased, owing to their unique ability to engage biological targets. We present the first example of PIFA-mediated dearomative spirocyclization of phenol-tethered pyrazoles, highlighting intramolecular trapping by the pyrazole moiety. This method efficiently affords a variety of spirocyclohexadienone-pyrazolo[3,4-b]piperidinones with yields of up to 82%. Mechanistic studies reveal that the dearomatization process involves a cationic intermediate.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2382-9631.
- Supporting Information
Publication History
Received: 17 June 2024
Accepted after revision: 08 August 2024
Accepted Manuscript online:
08 August 2024
Article published online:
12 September 2024
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