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Reductive Cyclization of o-Nitroarylated-α,β-unsaturated Aldehydes and Ketones with TiCl₃/HCl or Fe/HCl Leading to 1,2,3,9-Tetrahydro-4 H-carbazol-4-ones and Related Heterocycles

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dc.contributor.authorQiu, Yun
dc.contributor.authorDlugosch, Michael
dc.contributor.authorLiu, Xin
dc.contributor.authorKhan, Faiyaz
dc.contributor.authorWard, Jas
dc.contributor.authorLan, Ping
dc.contributor.authorBanwell, Martin
dc.date.accessioned2019-07-25T04:33:21Z
dc.date.issued2018
dc.date.updated2019-03-31T07:22:02Z
dc.description.abstractCompounds such as 3, the product of a palladium[0]-catalyzed Ullmann cross-coupling of o-iodonitrobenzene and 2-iodocyclohex-2-en-1-one, undergo complementary modes of reductive cyclization depending upon the conditions employed. Thus, on treatment with hydrogen in the presence of palladium on carbon, the tetrahydrocarbazole 4 is formed, while reaction of the same substrate (3) with TiCl3 in acetone affords the 1,2,3,9-tetrahydro-4H-carbazol-4-one 6.en_AU
dc.description.sponsorshipWe thank the Australian Research Council, the Institute of Advanced Studies, Jinan University, the Pearl River Scholar Program of Guangdong Province, and the Famous Foreign Supervisor Program (Grant 2018-HWMS001) of the Ministry of Education, People’s Republic of China, for financial support.en_AU
dc.format.mimetypeapplication/pdfen_AU
dc.identifier.issn0022-3263en_AU
dc.identifier.urihttp://hdl.handle.net/1885/164713
dc.language.isoen_AUen_AU
dc.provenancehttps://v2.sherpa.ac.uk/id/publication/7797..."The Accepted Version can be archived in a Non-Commercial Institutional Repository If Required by Funder, If Required by Institution. 12 months embargo " from SHERPA/RoMEO site (as at 6/01/2021). This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://dx.doi.org/10.1021/acs.joc.8b01940
dc.publisherAmerican Chemical Societyen_AU
dc.relationhttp://purl.org/au-research/grants/arc/DP170100926
dc.rights© 2018 American Chemical Societyen_AU
dc.sourceJournal of Organic Chemistryen_AU
dc.titleReductive Cyclization of o-Nitroarylated-α,β-unsaturated Aldehydes and Ketones with TiCl₃/HCl or Fe/HCl Leading to 1,2,3,9-Tetrahydro-4 H-carbazol-4-ones and Related Heterocyclesen_AU
dc.typeJournal articleen_AU
dcterms.accessRightsOpen Access
local.bibliographicCitation.issue19en_AU
local.bibliographicCitation.lastpage12033en_AU
local.bibliographicCitation.startpage12023en_AU
local.contributor.affiliationQiu, Yun, Jinan Universityen_AU
local.contributor.affiliationDlugosch, Michael, College of Science, ANUen_AU
local.contributor.affiliationLiu, Xin, College of Science, ANUen_AU
local.contributor.affiliationKhan, Faiyaz, College of Science, ANUen_AU
local.contributor.affiliationWard, James, College of Science, ANUen_AU
local.contributor.affiliationLan, Ping, Jinan Universityen_AU
local.contributor.affiliationBanwell, Martin, College of Science, ANUen_AU
local.contributor.authoruidDlugosch, Michael, u5663327en_AU
local.contributor.authoruidLiu, Xin, u6180982en_AU
local.contributor.authoruidKhan, Faiyaz, u5180284en_AU
local.contributor.authoruidWard, James, u4431856en_AU
local.contributor.authoruidBanwell, Martin, u9500594en_AU
local.description.notesImported from ARIESen_AU
local.identifier.absfor030503 - Organic Chemical Synthesisen_AU
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciencesen_AU
local.identifier.ariespublicationu4485658xPUB1276en_AU
local.identifier.citationvolume83en_AU
local.identifier.doi10.1021/acs.joc.8b01940en_AU
local.identifier.scopusID2-s2.0-85053834758
local.publisher.urlhttps://pubs.acs.org/en_AU
local.type.statusAccepted Versionen_AU

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