170956-93-1

Upstream product

• 201230-82-2 carbon monoxide 
• 157869-15-3 2-((4-methoxyphenyl)ethynyl)aniline 
• 55160-02-6 3-(4-methoxybenzylidene)indolin-2-one 
• 91-56-5 indole-2,3-dione 
• 59-48-3 2-oxoindole 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 1003321-12-7 (2S,3S)-ethyl 2-[3-(4-methoxybenzyl)-2-oxoindolin-3-yl]-3,3,3-trifluoro-2-hydroxypropanoate 
• 1003321-23-0 (2R,3R)-ethyl 2-[3-(4-methoxybenzyl)-2-oxoindolin-3-yl]-3,3,3-trifluoro-2-hydroxypropanoate 
• 1185774-45-1 (S)-diisopropyl 1-(3-(4-methoxybenzyl)-2-oxoindolin-3-yl)hydrazine-1,2-dicarboxylate 
• 1310861-68-7 (R)-3-(hydroxy(phenyl)amino)-3-(4-methoxybenzyl)indolin-2-one 
• 1269105-79-4 (S)-3-(hydroxy(phenyl)amino)-3-(4-methoxybenzyl)indolin-2-one 
• 1304075-30-6 (3R)-3-(4-methoxybenzyl)-3-((1S)-3-oxocyclohexyl)-2-oxoindole 
• 1376933-01-5 3-(4-methoxybenzyl)-3-(phenylthio)indolin-2-one 
• 1376933-03-7 3-(4-methoxybenzyl)-1,3-bis(phenylthio)indolin-2-one 
• 1376933-02-6 (R)-3-(4-methoxybenzyl)-3-(phenylthio)indolin-2-one 
• 1376933-52-6 (R)-3-(4-methoxybenzyl)-3-(phenylsulfonyl)indolin-2-one 

Relevant academic research and scientific papers

Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols

A general and efficient iron-catalyzed C-alkylation of oxindoles has been developed. This borrowing hydrogen approach employing a (cyclopentadienone)iron carbonyl complex (2 mol %) exhibited a broad reaction scope, allowing benzylic and simple primary and secondary aliphatic alcohols to be employed as alkylating agents. A variety of oxindoles underwent selective mono-C3-alkylation in good-to-excellent isolated yields (28 examples, 50–92 % yield, 79 % average yield).

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.).

Transition-metal-free Chemoselective Oxidative C?C Coupling of the sp3 C?H Bond of Oxindoles with Arenes and Addition to Alkene: Synthesis of 3-Aryl Oxindoles, and Benzofuro- and Indoloindoles

A transition-metal (TM)-free and halogen-free NaOtBu-mediated oxidative cross-coupling between the sp3 C?H bond of oxindoles and sp2 C?H bond of nitroarenes has been developed to access 3-aryl substituted and 3,3-aryldisubstituted oxindoles in DMSO at room temperature in a short time. Interestingly, the sp3 C?H bond of oxindoles could also react with styrene under TM-free conditions for the practical synthesis of quaternary 3,3-disubstituted oxindoles. The synthesized 3-oxindoles have also been further transformed into advanced heterocycles, that is, benzofuroindoles, indoloindoles, and substituted indoles. Mechanistic experiments of the reaction suggests the formation of an anion intermediate from the sp3 C?H bond of oxindole by tert-butoxide base in DMSO. The addition of nitrobenzene to the in-situ generated carbanion leads to the 3-(nitrophenyl)oxindolyl carbanion in DMSO which is subsequently oxidized to 3-(nitro-aryl) oxindole by DMSO.

Transition-Metal-Free C-H Hydroxylation of Carbonyl Compounds

Transition metal and reductant free α-C(sp3)-H hydroxylation of carbonyl compounds are reported. This method is promoted by commercially available inexpensive KO-t-Bu and atmospheric air as an oxidant at room temperature. This unified strategy is also very facile for hydroxylation of various carbonyl compound derivatives to obtain quaternary hydroxyl compounds in excellent yield. A preliminary mechanistic investigation, supported by isotope labeling and computational studies, suggests the formation of a peroxide bond and its cleavage by in situ generated enolate.

Pd/C-catalyzed alkylation of heterocyclic nucleophiles with alcohols through the "borrowing hydrogen" process

The alkylation of heterocyclic compounds is important for the synthesis of various biologically active compounds. In this paper, we present the development of a Pd/C-catalyzed alkylation of heterocyclic compounds using alcohols as the alkylating agents. T

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.

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.

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

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.