70452-25-4

Upstream product

• 91-56-5 indole-2,3-dione 
• 122-00-9 para-methylacetophenone 
• 59-48-3 2-oxoindole 
• 54731-27-0 1-p-methylphenyl-1-trimethylsiloxyethene 
• 13422-78-1 3-oxo-3-p-toluoylpropanoic acid 

Downstream Products

• 66447-80-1 3-[2-(4-methylphenyl)-2-oxoethylidene]-1,3-dihydro-2H-indol-2-one 
• 66447-80-1 (Z)-3-(2-oxo-2-(p-tolyl)ethylidene)indolin-2-one 

Relevant academic research and scientific papers

Oxidative ring expansion of 3-hydroxy-3-phenacyloxindoles using phenyliodine diacetate and molecular iodine: Synthesis of 2-hydroxy-2-aryl/alkyl-2,3-dihydroquinolin-4(1H)-ones

Oxidation of tertiary alcohol of the type 3-hydroxy-3-phenacyloxindoles using the combination of phenyliodine diacetate and molecular iodine in methanol results in oxidative cleavage of C2-C3 bond to form isocyanate as an intermediate with its subsequent

Diastereoselective trans Cyclopropanation of 3-Alkylidene Oxindoles with in Situ Generated α-Diazo Carbonyls or α,β-Unsaturated Diazo Compounds

An efficient diastereoselective trans cyclopropanation of 3-alkylidene oxindoles with in situ generated α-diazo carbonyl compounds or α,β-unsaturated diazo compounds under metal-free conditions has been developed to synthesize 3-spirocyclopropyl-2-oxindol

The Ligand Free Palladium(II)-Catalyzed Regioselective 1,2-Addition of Enol Silanes to Quinones to Access 4-Hydroxy-4-(2-oxo-2-arylethyl)cyclohexadien-1-ones and Synthetic Applications

In contrast to the conventional 1,4-addition process, regioselective 1,2-addition of silyl enol ethers to quinones can now be achieved via a palladium(II) enolate pathway that provides access to 4-hydroxy-4-(2-oxo-2-arylethyl)cyclohexa-2,5-dien-1-one derivatives. This quinone alkylation protocol proceeds under mild reaction conditions at ambient temperature under open air and does not require either an external ligand for the palladium or the use of a base. Additionally, the cyclohexadienone products have been exploited as synthetic precursors for the construction of fused heteroaryl systems.

"on Water" Catalytic Aldol Reaction between Isatins and Acetophenones: Interfacial Hydrogen Bonding and Enamine Mechanism

"On water" catalytic aldol reaction catalyzed by polyetheramine (D230) has been developed for easy access to 3-substituted 3-hydroxyindolin-2-ones through the reaction between various substituted isatins and acetophenones/cyclic ketones in high yields under room temperature. Systematic mechanism investigation uncovers the secret for the on water catalytic aldol reaction: comparison of the heterogeneous and homogeneous reaction circumstances with yields of 95 and 20%, respectively, indicates the on-water reaction dominating; interfacial hydrogen bonding between isatin with H2O is tested based on the downfield shift of the C2 and C3's 13C NMR signals when water was added to the CDCl3 solution of isatin; Lewis base polyetheramine D230 catalyzes the aldol reaction via the enamine mechanism verified by in situ NMR and ESI-MS analysis.

Synthesis and biological evaluation of 3-substituted 2-oxindole derivatives as new glycogen synthase kinase 3β inhibitors

Glycogen synthase kinase 3β (GSK-3β) is a widely investigated molecular target for numerous diseases including Alzheimer's disease, cancer, and diabetes mellitus. Inhibition of GSK-3β activity has become an attractive approach for treatment of diabetes and cancer. We report the discovery of novel GSK-3β inhibitors of 3-arylidene-2-oxindole scaffold with promising activity. The most potent compound 3a inhibits GSK-3β with IC50 4.19 nM. In a cell-based assay 3a shows no significant leucocyte toxicity at 10 μM and is moderately cytotoxic against A549 cells. Compound 3a demonstrated high antidiabetic efficacy in obese streptozotocin-treated rats improving glucose tolerance at a dose of 50 mg/kg body weight thus representing an interesting lead for further optimization.

An efficient and direct synthesis of substituted 2-phenylquinoline-4-carboxamides from 3-substituted-3-hydroxyindolin-2-ones

A simple and direct synthesis of substituted 2-phenylquinoline-4-carboxamides from 3-substituted-3-hydroxyindolines in presence of ammonium acetate is described. The developed protocol also allows synthesis of the carboxamide moeity directly from isatin a

DABCO-catalyzed synthesis of 3-substituted-3-hydroxyindolin-2-ones in aqueous media

An efficient and greener protocol for easy access to 3-susbstituted-3-hydroxy-2-oxindoles by the reaction with various substituted isatins and acetophenones is described. This protocol is widely applicable for a variety of isatins and acetophenones using

Highly efficient regioselective synthesis of pyrroles via a tandem enamine formation-Michael addition-cyclization sequence under catalyst- and solvent-free conditions

A convenient catalyst-free, three-component procedure was developed for the synthesis of tetrasubstituted pyrroles under solvent-free conditions and in green solvents glycerol, PEG-200 and water. A sequential enamine-formation, Michael addition and intram

C U 2O-Catalyzed C(SP 3)-H/C(SP 3)-H Cross-Coupling Using TEMPO: Synthesis of 3-(2-Oxoalkyl)-3-hydroxyoxindoles

A simple, convenient, and efficient oxidative cross-coupling reaction of oxindoles with ketones toward a variety of 3-(2-oxoalkyl)-3-hydroxyoxindoles in moderate to excellent yields has been developed. This transformation proceeds via a tandem oxidative cross-coupling by using 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) in air as an environmentally benign oxidant. This methodology provides an alternative approach for the direct generation of all-carbon quaternary centers at the C3 position of oxindoles.

Molecular sieve mediated decarboxylative Mannich and aldol reactions of β-ketoacids

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.