Tandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium salts
dc.bibliographicCitation.firstPage | 1119 | eng |
dc.bibliographicCitation.journalTitle | Beilstein Journal of Organic Chemistry | eng |
dc.bibliographicCitation.volume | 9 | eng |
dc.contributor.author | Kiamehr, M. | |
dc.contributor.author | Moghaddam, F.M. | |
dc.contributor.author | Mkrtchyan, S. | |
dc.contributor.author | Semeniuchenko, V. | |
dc.contributor.author | Supe, L. | |
dc.contributor.author | Villinger, A. | |
dc.contributor.author | Langer, P. | |
dc.contributor.author | Laroshenko, V.O. | |
dc.date.accessioned | 2020-09-11T12:53:01Z | |
dc.date.available | 2020-09-11T12:53:01Z | |
dc.date.issued | 2013 | |
dc.description.abstract | The 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.version | publishedVersion | eng |
dc.identifier.uri | https://doi.org/10.34657/4289 | |
dc.identifier.uri | https://oa.tib.eu/renate/handle/123456789/5660 | |
dc.language.iso | eng | eng |
dc.publisher | Frankfurt, M. : Beilstein-Institut zur Förderung der Chemischen Wissenschaften | eng |
dc.relation.doi | https://doi.org/10.3762/bjoc.9.124 | |
dc.relation.issn | 1860-5397 | |
dc.rights.license | CC BY 2.0 Unported | eng |
dc.rights.uri | https://creativecommons.org/licenses/by/2.0/ | eng |
dc.subject.ddc | 530 | eng |
dc.subject.other | Cyclization | eng |
dc.subject.other | Density functional calculations | eng |
dc.subject.other | Heterocycles | eng |
dc.subject.other | Nucleophilic addition | eng |
dc.subject.other | Pyridinium salt | eng |
dc.title | Tandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium salts | eng |
dc.type | Article | eng |
dc.type | Text | eng |
tib.accessRights | openAccess | eng |
wgl.contributor | LIKAT | eng |
wgl.subject | Physik | eng |
wgl.type | Zeitschriftenartikel | eng |
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