5796-80-5Relevant academic research and scientific papers
Highly efficient asymmetric bioreduction of 1-aryl-2-(azaaryl)ethanones. Chemoenzymatic synthesis of lanicemine
Liz, Ramón,Liardo, Elisa,Rebolledo, Francisca
, p. 8214 - 8220 (2019)
Different ketoreductases (KREDs) have been used to promote a highly selective reduction of several 1-aryl-2-(azaaryl)ethanones (azaaryl = pyridinyl, quinolin-2-yl), the corresponding secondary alcohols being obtained with very high yields and enantiomeric excesses (ee > 99%). The absolute configuration of each optically active alcohol has been assigned by means of modified Mosher and Kelly methods, two shielding effects being evaluated: (1) the Mosher phenyl ring effect on the azaaryl protons and (2) the one of the azaaryl ring on the Mosher methoxy group. In addition, the biologically active amine lanicemine has been synthesized from (R)-1-phenyl-2-(pyridin-2-yl)ethanol, thus proving the utility of the secondary alcohols here prepared.
Tautomer-selective derivatives of enolate, ketone and enaminone by addition reaction of picolyl-type anions with nitriles
Bai, Jianliang,Wang, Peng,Cao, Wei,Chen, Xia
, p. 645 - 652 (2016/09/28)
We describe an efficient for the synthesis of compounds of tautomeric β-pyridyl/quinolyl-enol, -ketone, -enaminone, which were finally characterized by standard methods like NMR, IR or SCXRD. The addition reaction of lithiated intermediates of picoline, 2-ethylpyridine and 2-methylquinoline, respectively, with nitriles followed by acid hydrolysis afforded the corresponding tautomeric compounds of enol, ketone and emaminone. Interestingly, treatment of 2-methylpyridine or 2-ethylpyridine with nitriles, respectively, yielded mostly β-pyridyl ketone and enol tautomers without enaminones, while 2-methylquinoline with nitriles gave β-quinolyl ketone and enaminone tautomers without enols. The reaction of 2-benzylpyridine with nitriles was not available under the same conditions.
One-pot synthesis of quinoline derivatives using choline chloride/tin (II) chloride deep eutectic solvent as a green catalyst
Shahabi, Dana,Tavakol, Hossein
, p. 324 - 328 (2016/05/19)
In this work, various quinoline derivatives were prepared efficiently through a one-pot, three component synthesis using choline chloride/tin(II) chloride (ChCl·2SnCl2) deep eutectic solvent (DES) as a green catalyst. The procedure is free of using toxic solvents or catalyst and it could be categorized as a green method. In this procedure, aniline derivatives, aromatic aldehydes and enolizable aldehydes were mixed in the presence of DES that plays both roles of solvent and the reaction catalyst. Using this methodology, quinoline derivatives were synthesized simply at 60 °C in 2-3 h with high yields (54-97%). All products were purified by chromatography and recrystallization in ethanol. The employed DES have been recycled 4 time without important loss of its activity.
