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Synthesis of 2‐Aryl‐5‐Nitropyridines by Three‐Component Ring Transformation of 3,5‐Dinitro‐2‐Pyridone
Author(s) -
Le Thi Song,
Asahara Haruyasu,
Kobiro Kazuya,
Sugimoto Ryuichi,
Saigo Kazuhiko,
Nishiwaki Nagatoshi
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300282
Subject(s) - chemistry , aromatization , ammonium acetate , ring (chemistry) , aryl , component (thermodynamics) , transformation (genetics) , medicinal chemistry , ammonium , organic chemistry , combinatorial chemistry , catalysis , gene , thermodynamics , biochemistry , alkyl , high performance liquid chromatography , physics
Abstract 2‐Arylated‐5‐nitropyridines were efficiently synthesized by a three‐component ring transformation of 3,5‐dinitro‐2‐pyridone with aromatic ketones in the presence of ammonium acetate, in which the dinitropyridone serves as a synthetic equivalent of an unstable nitromalonaldehyde. Although a 2,8‐diazabicyclo[3.3.1]non‐3‐ene derivative was also formed as a byproduct, it was converted into nitropyridines under the reaction conditions, heating in the presence of ammonium acetate. This experimental fact implies that the former compound is a kinetically controlled product and the latter is a thermodynamically controlled product because of the aromatization. This method is applicable to various kinds of aryl and (hetero)aryl ketones to afford the corresponding (hetero)arylated pyridines in good to excellent yields.