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

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)


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
Publication statusPublished - 2009


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