84003-25-8Relevant academic research and scientific papers
Scope, Limitations and Mechanistic Analysis of the HyperBTM-Catalyzed Acylative Kinetic Resolution of Tertiary Heterocyclic Alcohols**
Cheong, Paul Ha-Yeon,Cordes, David B.,Feoktistova, Taisiia,Greenhalgh, Mark D.,Slawin, Alexandra M. Z.,Smith, Andrew D.,Smith, Samuel M.,Taylor, James E.,Walden, Daniel M.
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.
Autoxidation/Aldol Tandem Reaction of 2-Oxindoles with Ketones: A Green Approach for the Synthesis of 3-Hydroxy-2-Oxindoles
Zhang, Qing-Bao,Jia, Wen-Liang,Ban, Yong-Liang,Zheng, Yong,Liu, Qiang,Wu, Li-Zhu
, p. 2595 - 2598 (2016/02/27)
In the presence of tetrabutylammonium fluoride and molecular sieves (MS) 4 ? in DMF, an efficient autoxidation reaction of 2-oxindoles with ketones under air at room temperature has been developed. This approach may provide a green, practical, and metal-free protocol for a wide range of biologically important 3-hydroxy-3-(2-oxo-alkyl)-2-oxindoles.
Discovery of 3-Hydroxy-3-phenacyloxindole Analogues of Isatin as Potential Monoamine Oxidase Inhibitors
Tripathi, Rati K. P.,Krishnamurthy, Sairam,Ayyannan, Senthil R.
, p. 119 - 132 (2016/01/15)
A series of 3-hydroxy-3-phenacyloxindole analogues of isatin were designed, synthesized, and evaluated in vitro for their inhibitory activity toward monoamine oxidase (MAO) A and B. Most of the synthesized compounds proved to be potent and selective inhibitors of MAO-A rather than MAO-B. 1-Benzyl-3-hydroxy-3-(4′-hydroxyphenacyl)oxindole (compound 18) showed the highest MAO-A inhibitory activity (IC50: 0.009±0.001 μm, Ki: 3.69±0.003 nm) and good selectivity (selectivity index: 60.44). Kinetic studies revealed that compounds 18 and 16 (1-benzyl-3-hydroxy-3-(4′-bromophenacyl)oxindole) exhibit competitive inhibition against MAO-A and MAO-B, respectively. Structure-activity relationship studies suggested that the 3-hydroxy group is an essential feature for these analogues to exhibit potent MAO-A inhibitory activity. Computational studies revealed the possible molecular interactions between the inhibitors and MAO isozymes. The computational data obtained are congruent with experimental results. Further studies on the lead inhibitors, including co-crystallization of inhibitor-MAO complexes and in vivo evaluations, are essential for their development as potential therapeutic agents for the treatment of MAO-associated neurological disorders.
Molecular sieve mediated decarboxylative Mannich and aldol reactions of β-ketoacids
Zhong, Fangrui,Jiang, Chunhui,Yao, Weijun,Xu, Li-Wen,Lu, Yixin
supporting information, p. 4333 - 4336 (2013/07/26)
A molecular sieve mediated decarboxylative Mannich reaction of β-ketoacids with sulfonyl imines is reported; this protocol leads to an efficient preparation of synthetically useful β-amino ketones. An analogous molecular sieve promoted decarboxylative aldol reaction between β-ketoacids and isatins is also described, which affords bioactive 3-substituted-3-hydroxy-oxindoles in excellent yields.
A versatile synthetic methodology for the synthesis of tryptophols
Garden, Simon J,Da Silva, Rosangela B,Pinto, Angelo C
, p. 8399 - 8412 (2007/10/03)
Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol.
