1335242-96-0Relevant articles and documents
Autocatalytic synthesis of 3-ethyl-3-hydroxy-indole-2-ones and their neuroprotection and antitumor activities’ evaluation
Chen, Gang,Lin, Jiao,Zhang, Jie,Wu, Ya,Gu, Xuefan,Hao, Xiaojiang,Zhang, Yu
, p. 471 - 474 (2018)
In this study, a series of 3-ethyl-3-hydroxy-indole-2-ones were synthesized through the addition reaction of Et2Zn and N-substituted isatin by an autocatalytic process. The synthesized compounds were characterized by NMR spectroscopy and mass spectrometry, and the reaction mechanism was discussed. The antitumor and neuroprotection activities of these compounds were evaluated. The results showed that several compounds display protection activity on H2O2-induced apoptosis of PC12 cells, which are more effective than that of (±)-α-tocopherol Vitamin E (VE). Moreover, these compounds also show antitumor activity against A549 and P388 cell lines.
Scope, Limitations and Mechanistic Analysis of the HyperBTM-Catalyzed Acylative Kinetic Resolution of Tertiary Heterocyclic Alcohols**
Smith, Samuel M.,Greenhalgh, Mark D.,Feoktistova, Taisiia,Walden, Daniel M.,Taylor, James E.,Cordes, David B.,Slawin, Alexandra M. Z.,Cheong, Paul Ha-Yeon,Smith, Andrew D.
supporting information, (2021/11/16)
The full scope and limitations of the catalytic acylative kinetic resolution of a range of tertiary heterocyclic alcohols (78 examples, s up to >200) is reported under operationally-simple conditions, using low loadings of a commercially available Lewis basic isothiourea catalyst, HyperBTM (generally 1 mol %). The protocol is highly effective for the kinetic resolution of 3-substituted 3-hydroxyoxindole and α-substituted α-hydroxylactam derivatives bearing up to three potential recognition motifs at the stereogenic tertiary carbinol center. The full power of this methodology has been showcased through the synthesis of highly enantioenriched biologically-active target compounds in both enantiomeric forms. To provide further insight into the reaction mechanism, a detailed kinetic analysis of this Lewis base-catalyzed acylation of tertiary alcohols is reported using the variable time normalization analysis (VTNA) method.
Oxygen-involved oxidative deacetylation of α-substituted β-acetyl amides - Synthesis of α-Keto amides
Li, Dianjun,Yu, Wei
supporting information, p. 3708 - 3714 (2014/01/06)
α-Substituted β-acetyl amides could undergo C-C bond cleavage to form α-keto amides when treated with copper(II) chloride (CuCl 2) and boron trifluoride diethyl etherate (BF3× OEt2) under an oxygen atmosphere. The yield can be increased by the addition of tert-butyl hydroperoxide which alone can also effect the reaction. The reaction provides a new protocol for the synthesis of α-keto amides. Copyright
Regio- and diastereoselective C-C coupling of α-olefins and styrenes to 3-hydroxy-2-oxindoles by ru-catalyzed hydrohydroxyalkylation
Yamaguchi, Eiji,Mowat, Jeffrey,Luong, Tom,Krische, Michael J.
supporting information, p. 8428 - 8431 (2013/09/02)
The direct approach: Ruthenium(0)-catalyzed hydrohydroxyalkylation of α-olefins and styrenes with 3-hydroxy-2-oxindoles forms branched products of C-C coupling with high levels of diastereocontrol. A mechanism involving diene-olefin oxidative coupling and a subsequent carboxylic acid co-catalyzed transfer hydrogenolysis of the resulting oxaruthenacycle intermediate is postulated. Copyright
Catalyst-free synthesis of 3-hydroxy-3-(alkyl/aryl)indolin-2-ones by addition of organoaluminum reagents to isatins
Kumar, G. Santosh,Ramesh, Palakuri,Kumar, A. Sanjeeva,Swetha,Meshram
, p. 5048 - 5051 (2013/08/28)
An efficient synthesis of 3-hydroxy-3-(alkyl/aryl)indol-2-one derivatives has been described by the reactions of isatin with organoaluminum reagents. The reaction is very rapid and yields are high. The protocol is applicable for substituted isatins as well as a variety of organoaluminums.
Kinetic resolution of tertiary alcohols: Highly enantioselective access to 3-hydroxy-3-substituted oxindoles
Lu, Shenci,Poh, Si Bei,Siau, Woon-Yew,Zhao, Yu
supporting information, p. 1731 - 1734 (2013/04/10)
Enantioselective: The first highly enantioselective kinetic resolution of 3-hydroxy-3-substituted oxindoles has been developed through oxidative esterification catalyzed by a N-heterocyclic carbene (see picture). This method uses a simple procedure and provides 3-hydroxy-oxindoles with various substituents at the 3-position in excellent enantiopurity. S=selectivity. Copyright
Trifluoroacetic acid-promoted synthesis of 3-hydroxy, 3-amino and spirooxindoles from α-keto-N-anilides
Gorokhovik, Ioulia,Neuville, Luc,Zhu, Jieping
supporting information; experimental part, p. 5536 - 5539 (2012/01/03)
Ketoanilides containing alkyl side chains were readily cyclized to 3-hydroxy-2-oxindoles or spirooxindoles by a single or double intramolecular Friedel-Crafts reaction in the presence of trifluoroacetic acid (TFA) at room temperature or at 45 °C. α-Iminoc
