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

Bulletin of the Korean chemical society

Ali Morsali¹  Shahriar Khadem¹  Abolghasem Davoodnia¹  Paria Attar¹  Hossein Eshghi¹  Niloofar Tavakoli-Hoseini¹ 

关键词: Brønsted-acidic ionic liquids;    3-Cyanopyridines;    3-Cyanopyridinones;    Multicomponent reactions;    Tautomerism;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

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.

【 授权许可】

Unknown