131609-35-3

Upstream product

• 3335-90-8 3-(4-chlorobenzylidene)indolin-2-one 
• 29551-52-8 3-[(E)-(4-chlorophenyl)methylidene]-1,3-dihydro-2H-indol-2-one 
• 59-48-3 2-oxoindole 
• 104-88-1 4-chlorobenzaldehyde 
• 91-56-5 indole-2,3-dione 
• 873-76-7 para-Chlorobenzyl alcohol 

Downstream Products

• 1185774-43-9 (S)-diisopropyl 1-(3-(4-chlorobenzyl)-2-oxoindolin-3-yl)hydrazine-1,2-dicarboxylate 
• 1310861-78-9 (R)-3-(4-chlorobenzyl)-3-(hydroxy(phenyl)amino)indolin-2-one 
• 1398681-32-7 benzaldehyde O-3-(4-chlorobenzyl)-2-oxoindolin-3-yl oxime 
• 1398681-63-4 3-bromo-3-(4-chlorobenzyl)indolin-2-one 
• 1376933-17-3 (R)-3-(4-chlorobenzyl)-3-(phenylthio)indolin-2-one 

Relevant academic research and scientific papers

C-3 alkylation of oxindole with alcohols catalyzed by an indene-functionalized mesoporous iridium catalyst

A heterogeneous indene-based iridium catalyst with a highly ordered dimensional-hexagonal mesostructure was prepared through complexation of IrCl3 with the indene-functionalized SBA-15 silica materials. During C-3 alkylation of oxindole with va

3-aryl-indolinones derivatives as antiplasmodial agents: synthesis, biological activity and computational analysis

Malaria is an infectious illness, affecting vulnerable populations in Third World countries. Inspired by natural products, indole alkaloids have been used as a nucleus to design new antimalarial drugs. So, eighteen oxindole derivatives, aza analogues were obtained with moderate to excellent yields. Also, the saturated derivatives of oxindole and aza derivatives via H2/Pd/C reduction were obtained in good yields, leading to racemic mixtures of each compound. Next, the inhibitory activity against P. falciparum of 18 compounds were tested, founding six compounds with IC50 20 μM. The most active of these compounds was 8c; however, their unsaturated derivative 7c was inactive. Then, a structure-activity relationship analysis was done, founding that focused LUMO lobe on the specific molecular zone is related to inhibitory activity against P. falciparum. Finally, we found a potential inhibition of lactate dehydrogenase by oxindole derivatives, using molecular docking virtual screening.

Chiral N,N′-Dioxide/Scandium(III)-Catalyzed Asymmetric Alkylation of N-Unprotected 3-Substituted Oxindoles

An efficient enantioselective alkylation of N-unprotected 3-substituted oxindoles was realized by using a chiral N,N′-dioxide/scandium(III) complex as the catalyst. A wide range of 3,3-dialkyl substituted oxindoles with quaternary stereocenters were obtained in high yields and ee values (up to 98% yield and 99% ee). (Figure presented.).

C-3 alkylation of oxindole with alcohols by Pt/CeO2 catalyst in additive-free conditions

In a series of transition metal-loaded CeO2 catalysts and Pt-loaded catalysts on various supports, Pt-loaded CeO2 shows the highest activity for the selective C-3 alkylation of oxindole with octanol. The catalyst is effective for alkylation of oxindole and N-substituted oxindole with a series of substituted benzyl, linear, hetero-aryl alcohols under additive-free conditions and is recyclable. Our results demonstrate the first additive-free catalytic system for this reaction. Mechanistic studies show that this system is driven by the borrowing-hydrogen pathway. Structure-activity relationship studies show that co-presence of surface Pt0 species on Pt metal clusters and basic support is indispensable for this catalytic system. This journal is the Partner Organisations 2014.

A Facile Method for the Synthesis of 3-Alkyloxindole

Benzylamine in combination with acetic acid was identified as a powerful catalyst for the condensation of oxindole with aldehydes, acetone or cyclic ketones. A variety of 3-alkyloxindoles could be readily prepared in 10 mmol scale via the sequential benzylamine acetate catalyzed condensation of oxindoles with aldehydes (or ketones) and conjugate reduction by NaBH4.

Organocatalytic enantioselective stereoablative hydroxylation of 3-halooxindoles: An effective method for the construction of enantioenriched 3-substituted 3-hydroxy-2-oxindoles

3-Substituted oxindoles as electrophilic partners: An unprecedented method for the construction of hydroxylated 3-substituted oxindoles in high yields and excellent enantioselectivities through stereoablative hydroxylation of 3-halooxindoles with an organocatalyst has been developed. This process not only differs from the common convention of using 3-substituted oxindoles as nucleophiles, but also provides a viable entry to optically active 3-substituted 3-hydroxy-2-oxindoles (see scheme).

Identification of indoline-2-thione analogs as novel potent inhibitors of α-melanocyte stimulating hormone induced melanogenesis

Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione compounds (3a-g) exhibited an effective inhibitory activity on melanin synthesis. The Structure-Activity Relationship (SAR) studies of 2 have revealed that in potent inhibitor 3a (>100% inhibition at 30μM, IC50=1.40μM) the role of nitrogen (3-N) at 3-position is insignificance. In addition, the hydrophobic substituents of 3 were better than the hydrophilic one. However, conversion of thione (-C=S, 3) to thiol (-C-SH, 4) led to decrease in the potency.

Highly enantioselective and organocatalytic α-amination of 2-Oxindoles

Figur Presented An effective method for the asymmetric synthesis of 3-amino-2-oxindoles was developed. The tetrasubstituted chiral carbon center was generated by asymmetric amination of N-unprotected 2-oxindoles with azodicarboxylate catalyzed by commercial biscinchona alkaloids in good to excellent yields with high enantioselectivities.

Ruthenium-catalyzed alkylation of oxindole with alcohols

(Chemical Equation Presented) An atom-economical and solvent-free catalytic procedure for the mono-3-alkylation of oxindole with alcohols is described. The reaction is mediated by the in situ generated catalyst from RuCl 3·xH2O and P

Iridium catalysed C-3 alkylation of oxindole with alcohols under solvent free thermal or microwave conditions

Ir-catalysed alkylation of oxindole and N-methyl oxindole with a range of substituted benzyl and heteroaryl alcohols under solvent free thermal or microwave conditions afforded the corresponding C-3-monoalkylated products in high to excellent yield.