Novel spiro fused heterocycles from the allylation of indigo

M.K. Abdel-Hamid, J.B. Bremner, J. Coates, P.A. Keller, C. Milander, Y.S. Torkamani, Brian Skelton, Allan White, A.C. Willis

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Abstract

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 use of thermal versus microwave heating.
Original languageEnglish
Pages (from-to)6947-6950
JournalTetrahedron Letters
Volume50
DOIs
Publication statusPublished - 2009

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Abdel-Hamid, M. K., Bremner, J. B., Coates, J., Keller, P. A., Milander, C., Torkamani, Y. S., ... Willis, A. C. (2009). Novel spiro fused heterocycles from the allylation of indigo. Tetrahedron Letters, 50, 6947-6950. https://doi.org/10.1016/j.tetlet.2009.09.098