1 results
Search Results
Now showing 1 - 1 of 1
- ItemTandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium salts(Frankfurt, M. : Beilstein-Institut zur Förderung der Chemischen Wissenschaften, 2013) Kiamehr, M.; Moghaddam, F.M.; Mkrtchyan, S.; Semeniuchenko, V.; Supe, L.; Villinger, A.; Langer, P.; Laroshenko, V.O.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.