72331-54-5Relevant academic research and scientific papers
α-Ketocarboxylic acid-based inhibitors of protein tyrosine phosphatases
Chen, Yen Ting,Onaran,Doss, Christopher J.,Seto, Christopher T.
, p. 1935 - 1938 (2007/10/03)
A series of aryl α-ketocarboxylic acids was synthesized and investigated as inhibitors for the protein tyrosine phosphatase from Yersinia enterocolitica. IC50 values for these compounds range from 79 to 2700 μM. Larger aromatic groups, and aromatic groups with high electron density, lead to more potent inhibitors. In general, the related aryl α-hydroxycarboxylic acids show lower activity.
Palladium-Catalyzed Double and Single Carbonylations of β-Amino Alcohols. Selective Synthesis of Morpholine-2,3-diones and Oxazolidin-2-ones and Applications for Synthesis of α-Oxo Carboxylic Acids
Imada, Yasushi,Mitsue, Yo,Ike, Kazuo,Washizuka, Ken-Ichi,Murahashi, Shun-Ichi
, p. 2079 - 2090 (2007/10/03)
Catalytic cross double carbonylation of secondary amines and alcohols proceeds in the presence of [PdCl2(MeCN)2] and CuI under carbon monoxide (80 atm) and oxygen (5 atm). Catalytic intramolecular double carbonylation of β-amino alcohols gives morpholine-2,3-diones, which are excellent protecting compounds of amino alcohols and important precursors for biologically active nitrogen compounds. In contrast, catalytic single carbonylation of β-amino alcohols under a mixture (1 : 1) of carbon monoxide and oxygen (1.0 atm) proceeds to give oxazolidin-2-ones selectively. The reaction can be explained by assuming a mechanism which includes intramolecular nucleophilic attack of the hydroxy group of (hydroxyethyl)aminocarbonyl ligands on the CO ligand of the carbamoylpalladium(II) complexes, followed by reductive elimination to give morpholine-2,3-diones. In contrast, direct nucleophilic attack of the hydroxy group to the carbamoyl group affords oxazolidin-2-ones. As a common intermediate for the double and single carbonylations, carbamoylpalladium(II) complex has been isolated by the reaction of [PdCl2(PMe3)2] with β-amino alcohol under CO. The present double carbonylation of amino alcohols provides a novel and convenient method for synthesis of α-oxo carboxylic acids. Thus, the morpholine-2,3-diones obtained undergo reaction with Grignard reagents chemoselectively at the ester positions to give 2-substituted 2-hydroxymorpholin-3-ones, which undergo acid hydrolysis to give α-oxo carboxylic acids.
REACTION OF FLUORINATED ARYLMAGNESIUM HALIDES WITH DI-TERT-BUTYL OXALATE
Shadrina, L. P.,Kazakov, A. F.,Dormidontov, Yu. P.,Pirogova, V. V.
, p. 2257 - 2259 (2007/10/02)
The reaction of phenylmagnesium halides fluorinated in the ring or in the side chain with di-tert-butyl oxalate was investigated.It was shown that the esters of arylglyoxalic or arylglycolic acids are formed under various temperature conditions, depending on the electrophilicity of the radical in the organomagnesium compound.
REACTION OF PENTAFLUOROPHENYLMAGNESIUM CHLORIDE WITH THE ESTERS OF DIBASIC ACIDS
Shadrina, L. P.,Dormidontov, Yu. P.
, p. 1251 - 1255 (2007/10/02)
In the reaction of pentafluorophenylmagnesium chloride with ethyl oxalate and ethyl dimethylmalonate the esters of secondary hydroxy acids are formed.In the reaction with ethyl succinate, glutarate, and adipate the esters of oxo acids are formed.It was shown that the character of the reaction products depends on the first dissociation constant of the respective acid.
