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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 6
BKCSDE 32(6)
June 20, 2011 

Experimental and Theoretical Studies on the Tautomerism in 2-Aminopyridines and 2(1H)-pyridinones: Synthesis of 2-Amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)pyridines and 4-Aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones
Abolghasem Davoodnia*, Paria Attar, Ali Morsali, Hossein Eshghi, Niloofar Tavakoli-Hoseini, Shahriar Khadem
Brønsted-acidic ionic liquids, 3-Cyanopyridines, 3-Cyanopyridinones, Multicomponent reactions, Tautomerism
Under solvent-free conditions and in one-pot, a series of 2-amino-4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)- pyridines and 4-aryl-3-cyano-6-(3,4-dimethoxyphenyl)-2(1H)-pyridinones were prepared using 3,4- dimethoxyacetophenone, an aldehyde, malononitrile (or ethyl cyanoacetate), and ammonium acetate in the presence of 3-methyl-1-(4-sulfonylbutyl)imidazolium hydrogen sulfate [HO3S(CH2)4MIM][HSO4] (a Brønsted acidic ionic liquid) as the catalyst in very short reaction time. The preference for the formation of more stable tautomers was consistence with the theoretical calculation using the Gaussian 03 program at the B3LYP hybrid density functional level.
1873 - 1878
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