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Novel spiro and fused heterocycles from the allylation of indigo

Abdel-Hamid, Mohammed K; Bremner, John B; Coates, Jonathan; Keller, Paul; Milander, Celia; Torkamani, Yasmine S; Skelton, Brian; White, Allan; Willis, Anthony


The allylation of indigo results in the one-step synthesis of two unique complex heterocyclic systems: a spiroindoline-pyridoindolone arising from the addition of three allyl moieties and a fused pyridoindolo-azepinoindolone generated from the addition and subsequent cyclisation of two allyl moieties. The structures of these novel heterocycles are assigned unambiguously using extensive NMR experiments and by X-ray crystallographic analysis. The distribution of the products is influenced by the...[Show more]

CollectionsANU Research Publications
Date published: 2009
Type: Journal article
Source: Tetrahedron Letters
DOI: 10.1016/j.tetlet.2009.09.098


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