Tandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium salts

dc.bibliographicCitation.firstPage1119eng
dc.bibliographicCitation.journalTitleBeilstein Journal of Organic Chemistryeng
dc.bibliographicCitation.volume9eng
dc.contributor.authorKiamehr, M.
dc.contributor.authorMoghaddam, F.M.
dc.contributor.authorMkrtchyan, S.
dc.contributor.authorSemeniuchenko, V.
dc.contributor.authorSupe, L.
dc.contributor.authorVillinger, A.
dc.contributor.authorLanger, P.
dc.contributor.authorLaroshenko, V.O.
dc.date.accessioned2020-09-11T12:53:01Z
dc.date.available2020-09-11T12:53:01Z
dc.date.issued2013
dc.description.abstractThe cyclization of cyclohexane-1,3-diones with various substituted pyridinium salts afforded functionalized 8-oxa-10-aza-tricyclo[7.3.1.0 2,7]trideca-2(7),11-dienes. The reaction proceeds by regioselective attack of the central carbon atom of the 1,3-dicar-bonyl unit to 4-position of the pyridinium salt and subsequent cyclization by base-assisted proton migration and nucleophilic addition of the oxygen atom to the 2-position, as was elucidated by DFT computations. Fairly extensive screening of bases and additives revealed that the presence of potassium cations is essential for formation of the product.eng
dc.description.versionpublishedVersioneng
dc.identifier.urihttps://doi.org/10.34657/4289
dc.identifier.urihttps://oa.tib.eu/renate/handle/123456789/5660
dc.language.isoengeng
dc.publisherFrankfurt, M. : Beilstein-Institut zur Förderung der Chemischen Wissenschafteneng
dc.relation.doihttps://doi.org/10.3762/bjoc.9.124
dc.relation.issn1860-5397
dc.rights.licenseCC BY 2.0 Unportedeng
dc.rights.urihttps://creativecommons.org/licenses/by/2.0/eng
dc.subject.ddc530eng
dc.subject.otherCyclizationeng
dc.subject.otherDensity functional calculationseng
dc.subject.otherHeterocycleseng
dc.subject.otherNucleophilic additioneng
dc.subject.otherPyridinium salteng
dc.titleTandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium saltseng
dc.typeArticleeng
dc.typeTexteng
tib.accessRightsopenAccesseng
wgl.contributorLIKATeng
wgl.subjectPhysikeng
wgl.typeZeitschriftenartikeleng
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