Department of Chemistry

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RH(III)-catalyzed fabrication of [4,3,1]-bridged azaheterocycles using quinone monoacetals
(ACS, 2025-06) Sakhuja, Rajeev
A rhodium-catalyzed annulation strategy for the fabrication of cyclohexanone-bridged indazolones and other related diazole-ones and diazine-ones was established using quionone monoacetals under mild conditions. On the other hand, the use of 4-hydroxy-4-methylcyclohexa-2,5-dienone under the optimized Rh-conditions produced an ortho-CAr-arylated product in moderate reactivity. Mechanistic studies suggested that the coupling proceeded via one-pot C–H activation-Michael/hetero-Michael additions into the enone moiety. Interestingly, the [4,3,1]-bridged-1,2-dihydro-3H-indazol-3-ones underwent unexpected migratory aromatization in acidic condition to produce 3-hydroxy-14H-benzo[c]indazolo[1,2-a]cinnolin-14-ones in high yields.
Reducing-Agent-Free Convergent Synthesis of Hydroxyimino-Decorated Tetracyclic Fused Cinnolines via RhIII-Catalyzed Annulation Using Nitroolefins
(ACS, 2021-01) Sakhuja, Rajeev
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.