Tandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium salts
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Date
2013
Volume
9
Issue
Journal
Beilstein Journal of Organic Chemistry
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Frankfurt, M. : Beilstein-Institut zur Förderung der Chemischen Wissenschaften
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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.
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Kiamehr, M., Moghaddam, F. M., Mkrtchyan, S., Semeniuchenko, V., Supe, L., Villinger, A., et al. (2013). Tandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium salts (Frankfurt, M. : Beilstein-Institut zur Förderung der Chemischen Wissenschaften). Frankfurt, M. : Beilstein-Institut zur Förderung der Chemischen Wissenschaften. https://doi.org//10.3762/bjoc.9.124
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CC BY 2.0 Unported