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Novel spiro and fused heterocycles from the allylation of indigo |
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| Authors: | Mohammed K Abdel-Hamid Jonathan Coates Celia Miländer Brian W Skelton Anthony C Willis |
| Institution: | a School of Chemistry University of Wollongong, Wollongong, NSW 2522, Australia b Avexa Limited, 576 Swan St, Richmond, Vic 3121, Australia c School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, Nedlands, WA 6009, Australia d Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia |
| 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. |
| Keywords: | Indigo Domino reaction Azepinoindolone Pyridoindolone Spiroindoline |
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