Title : ( 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 )
Authors: Abolghasem Davoodnia , Paria Attar , Ali Morsali , Hossein Eshghi , Niloofar Tavakoli-Hoseini , Shahriar Khadem ,
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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 [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.
Keywords
, Brønsted-acidic ionic liquids, 3-Cyanopyridines, 3-Cyanopyridinones, Multicomponent reactions, Tautomerism
@article{paperid:1022584,
author = {Abolghasem Davoodnia and Paria Attar and Ali Morsali and Eshghi, Hossein and Niloofar Tavakoli-Hoseini and Shahriar Khadem},
title = {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},
journal = {Bulletin of Korean Chemical Society},
year = {2011},
volume = {32},
number = {6},
month = {June},
issn = {0253-2964},
pages = {1873--1878},
numpages = {5},
keywords = {Brønsted-acidic ionic liquids; 3-Cyanopyridines; 3-Cyanopyridinones; Multicomponent reactions;
Tautomerism},
}
%0 Journal Article
%T 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
%A Abolghasem Davoodnia
%A Paria Attar
%A Ali Morsali
%A Eshghi, Hossein
%A Niloofar Tavakoli-Hoseini
%A Shahriar Khadem
%J Bulletin of Korean Chemical Society
%@ 0253-2964
%D 2011
