Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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

  • Davoodnia, Abolghasem (Department of Chemistry, Mashhad Branch, Islamic Azad University) ;
  • Attar, Paria (Department of Chemistry, Mashhad Branch, Islamic Azad University) ;
  • Morsali, Ali (Department of Chemistry, Mashhad Branch, Islamic Azad University) ;
  • Eshghi, Hossein (Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad) ;
  • Tavakoli-Hoseini, Niloofar (Department of Chemistry, Mashhad Branch, Islamic Azad University) ;
  • Khadem, Shahriar (Department of Chemistry, University of Ottawa)
  • Received : 2011.03.24
  • Accepted : 2011.04.07
  • Published : 2011.06.20
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Abstract

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 $[HO_3S(CH_2)_4MIM][HSO_4]$ (a Br${\o}$nsted 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.

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References

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