4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 3, Pages 2734-2747

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02729

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Funding

  1. Science and Engineering Research Board (SERB), New Delhi [EMR/2017/000598]
  2. BITS Pilani
  3. SERB, Pilani

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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.
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.

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