Tandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium salts.
作者： Mostafa Kiamehr , Firouz Matloubi Moghaddam , Satenik Mkrtchyan , Volodymyr Semeniuchenko , Linda Supe
DOI: 10.3762/BJOC.9.124
关键词: Cyclohexane 、 Chemistry 、 Carbon atom 、 Organic chemistry 、 Regioselectivity 、 Tandem 、 Medicinal chemistry 、 Potassium 、 Salt (chemistry) 、 Pyridinium 、 Nucleophilic addition
摘要: The cyclization of cyclohexane-1,3-diones with various substituted pyridinium salts afforded functionalized 8-oxa-10-aza-tricyclo[7.3.1.02,7]trideca-2(7),11-dienes. reaction proceeds by regioselective attack the central carbon atom 1,3-dicarbonyl unit to 4-position salt and subsequent base-assisted proton migration nucleophilic addition oxygen 2-position, as was elucidated DFT computations. Fairly extensive screening bases additives revealed that presence potassium cations is essential for formation product.
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