Rh(III)-Catalyzed (4 + 1) Annulation of Pyrazol-3-ones with Alkynoates via Ortho-Alkenylation/Cyclization Cascade: Synthesis of Indazole-Fused Pyrazoles

A facile synthesis of novel indazole-fused pyrazoles from pyrazol-3-ones and alkynoate esters/amides via Rh­(III)-catalyzed sequential C–H activation/ortho-alkenylation/intramolecular cyclization cascade is reported. The important characteristic of this method is that the resulting scaffold bearing...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-09, Vol.87 (18), p.12109-12114
Main Authors: Chiu, Wei-Jung, Chen, Hong-Ren, Barve, Indrajeet J., Sun, Chung-Ming
Format: Article
Language:English
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Summary:A facile synthesis of novel indazole-fused pyrazoles from pyrazol-3-ones and alkynoate esters/amides via Rh­(III)-catalyzed sequential C–H activation/ortho-alkenylation/intramolecular cyclization cascade is reported. The important characteristic of this method is that the resulting scaffold bearing quaternary carbon has been obtained through unusual [4 + 1] rather than expected [4 + 2] addition where alkynoate acts as a one-carbon unit.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01208