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Synthesis of Functionalized 1‐Benzamido‐1,4‐dihydropyridines via a One‐Pot Two‐Step Four‐Component Reaction
Author(s) -
Sun Jing,
Shen Guoliang,
Xie Yajing,
Yan Chaoguo
Publication year - 2014
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201400437
Subject(s) - chemistry , malononitrile , triethylamine , acetylenedicarboxylate , component (thermodynamics) , dimethyl acetylenedicarboxylate , base (topology) , catalysis , ethanol , organic chemistry , reaction conditions , proton nmr , medicinal chemistry , combinatorial chemistry , cycloaddition , mathematical analysis , physics , mathematics , thermodynamics
The one‐pot four‐component reaction of benzohydrazide, acetylenedicarboxylate, aromatic aldehydes and malononitrile in ethanol with triethylamine as base catalyst afforded functionalized 1‐benzamido‐1,4‐dihydropyridines in satisfactory yields. Under similar conditions, picolinohydrazide or nicotinohydrazide can also be successfully utilized in the reactions to give corresponding functionalized 1,4‐dihydropyridines. 1 H NMR data indicated that an equilibrium of cis/trans ‐conformations exist in 1‐benzamido‐1,4‐dihydropyridines.