Abstract
A novel synthetic protocol for the synthesis of [1,2- b]-fused bicyclic pyrazoles has been developed using radical cyclisation. The protocol uses cyclisation of pyrazole-1-(ω-alkyl) radicals generated from 1-[ω-(phenylselenyl)alkyl]-pyrazole precursors. The pyrazole natural product, withasomnine (3-phenyl-5,6-dihydro-4 H-pyrrolo[1,2- b]pyrazole), and larger ring analogues have been synthesised in good yield using the protocol. A Bu 3SnH-mediated oxidative cyclisation mechanism is facilitated by azo or Et 3B radical initiators acting as oxidants of the intermediate π-radicals.
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