Metal-Free Triple Annulation of Ene–Yne–Ketones with Isocyanides: Domino Access to Furan-Fused Heterocycles via Furoketenimine
journal contributionposted on 17.10.2018, 18:20 by Zhongyan Hu, Jinhuan Dong, Zhaoyang Li, Bo Yuan, Ruyue Wei, Xianxiu Xu
A new furoketenimine intermediate from the coupling of ene-yne-ketones and o-alkenyl arylisocyanides, which enables the efficient synthesis of a wide range of tetracyclic and pentacyclic furan-fused heterocycles in a one-pot domino process under catalyst-free conditions, is disclosed. Based on the control experiments, a cascade of 1,6-addition, cyclization, intramolecular Diels–Alder reaction, and oxidative aromatization was proposed for the mechanism.
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Enefuroketenimineintramolecularcontrol experimentspentacyclic furan-fused heterocyclescyclizationmechanismMetal-Free Triple AnnulationDielene-yne-ketonesynthesisIsocyanidecatalyst-free conditionsoxidative aromatizationalkenyl arylisocyanidesone-pot domino processFuroketenimineFuran-Fused HeterocyclestetracycliccascadeDomino Access