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Title: Tandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium salts
Authors: Kiamehr, M.Moghaddam, F.M.Mkrtchyan, S.Semeniuchenko, V.Supe, L.Villinger, A.Langer, P.Laroshenko, V.O.
Publishers Version: https://doi.org/10.3762/bjoc.9.124
Issue Date: 2013
Published in: Beilstein Journal of Organic Chemistry Vol. 9 (2013)
Publisher: Frankfurt, M. : Beilstein-Institut zur Förderung der Chemischen Wissenschaften
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.
Keywords: Cyclization; Density functional calculations; Heterocycles; Nucleophilic addition; Pyridinium salt
DDC: 530
License: CC BY 2.0 Unported
Link to License: https://creativecommons.org/licenses/by/2.0/
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