Reducing-Agent-Free Convergent Synthesis of Hydroxyimino-Decorated Tetracyclic Fused Cinnolines via RhIII-Catalyzed Annulation Using Nitroolefins

A mild Rh-catalyzed method was developed for the synthesis of hydroxyimino functionalized indazolo­[1,2-a]­cinnolines and phthalazino­[2,3-a]­cinnolines by reductive [4 + 2] annulation between 1-arylindazolones and 2-aryl-2,3-dihydrophthalazine-1,4-diones with varied nitroolefins. The targeted oxime...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-02, Vol.86 (3), p.2734-2747
Main Authors: Karishma, Pidiyara, Mahesha, Chikkagundagal K, Mandal, Sanjay K, Sakhuja, Rajeev
Format: Article
Language:English
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Summary:A mild Rh-catalyzed method was developed for the synthesis of hydroxyimino functionalized indazolo­[1,2-a]­cinnolines and phthalazino­[2,3-a]­cinnolines by reductive [4 + 2] annulation between 1-arylindazolones and 2-aryl-2,3-dihydrophthalazine-1,4-diones with varied nitroolefins. The targeted oxime decorated tetracyclic fused cinnolines were synthesized via sequential C–H activation/olefin insertion/reduction under reducing-agent-free conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02729