CC BY 2.0 UnportedKiamehr, M.Moghaddam, F.M.Mkrtchyan, S.Semeniuchenko, V.Supe, L.Villinger, A.Langer, P.Laroshenko, V.O.2020-09-112020-09-112013https://doi.org/10.34657/4289https://oa.tib.eu/renate/handle/123456789/5660The 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.enghttps://creativecommons.org/licenses/by/2.0/530CyclizationDensity functional calculationsHeterocyclesNucleophilic additionPyridinium saltArticle