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Novel spiro and fused heterocycles from the allylation of indigo

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dc.contributor.authorAbdel-Hamid, Mohammed K
dc.contributor.authorBremner, John B
dc.contributor.authorCoates, Jonathan
dc.contributor.authorKeller, Paul
dc.contributor.authorMilander, Celia
dc.contributor.authorTorkamani, Yasmine S
dc.contributor.authorSkelton, Brian
dc.contributor.authorWhite, Allan
dc.contributor.authorWillis, Anthony
dc.date.accessioned2015-12-10T22:32:34Z
dc.date.issued2009
dc.date.updated2016-02-24T10:23:14Z
dc.description.abstractThe 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. Crown
dc.identifier.issn0040-4039
dc.identifier.urihttp://hdl.handle.net/1885/55823
dc.publisherElsevier
dc.sourceTetrahedron Letters
dc.subjectKeywords: dye; heterocyclic compound; indigo; indigo carmine; indole derivative; unclassified drug; allylation; article; chemical structure; microwave irradiation; nuclear magnetic resonance; one pot synthesis; thermal exposure; X ray crystallography Azepinoindolone; Domino reaction; Indigo; Pyridoindolone; Spiroindoline
dc.titleNovel spiro and fused heterocycles from the allylation of indigo
dc.typeJournal article
local.bibliographicCitation.issue50
local.bibliographicCitation.lastpage6950
local.bibliographicCitation.startpage6947
local.contributor.affiliationAbdel-Hamid, Mohammed K, University of Wollongong
local.contributor.affiliationBremner, John B, University of Wollongong
local.contributor.affiliationCoates, Jonathan, Avexa Limited
local.contributor.affiliationKeller, Paul, University of Wollongong
local.contributor.affiliationMilander, Celia, University of Wollongong
local.contributor.affiliationTorkamani, Yasmine S, University of Wollongong
local.contributor.affiliationSkelton, Brian, University of Western Australia
local.contributor.affiliationWhite, Allan, University of Western Australia
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.contributor.authoruidWillis, Anthony, u8512028
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030606 - Structural Chemistry and Spectroscopy
local.identifier.absfor030502 - Natural Products Chemistry
local.identifier.absfor030599 - Organic Chemistry not elsewhere classified
local.identifier.ariespublicationu4005981xPUB341
local.identifier.citationvolume50
local.identifier.doi10.1016/j.tetlet.2009.09.098
local.identifier.scopusID2-s2.0-70350519042
local.identifier.thomsonID000271841900005
local.type.statusPublished Version

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