40940-16-7

Upstream product

• 26465-37-2 dimethyl 2-(2-nitrophenyl)malonate 
• 201230-82-2 carbon monoxide 
• 2437-05-0 ethyl 3-(2-nitrophenyl)acrylate 
• 612-41-9 2-nitrocinnamic acid 
• 21728-28-9 (2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester 
• 778-82-5 ethyl 3-indoleacetate 
• 91-56-5 indole-2,3-dione 
• 67520-95-0 hydroxy-(2-oxo-indolin-3-yl)-acetic acid ethyl ester 
• 65112-88-1 ethyl oxindole-3-glyoxalate 
• 17266-70-5 3-Acetylindol-2-one 
• 404597-64-4 2-methoxycarbonyl-2-(2-nitro-phenyl)-succinic acid 4-ethyl ester 1-methyl ester 
• 1493-27-2 ortho-nitrofluorobenzene 
• 404597-65-5 2-(2-nitro-phenyl)-succinic acid 4-ethyl ester 1-methyl ester 
• 21728-28-9 (E)-(2-oxo-1,2-dihydroindol-3-ylidene)acetic acid ethyl ester 

Downstream Products

• 1620145-20-1 ethyl 2-(1'-benzyl-3'-((tert-butoxycarbonyl)amino)-2,2'-dioxo-[3,3'-biindolin]-3-yl)acetate 
• 246867-17-4 2-oxo-1,2,3,4-tetrahydro-quinoline-3-carboxylic acid 

Relevant academic research and scientific papers

The reaction of isatin with alkoxycarbonylmethylene (triphenyl)phosphoranes

Isalin (1) reacted with alkoxycarbonylmethylene(triphenyl)phosphoranes (2) in boiling benzene for about 3 h to give orange yellow crystalline products of alkyl (1,2-dihydro-2-oxo-3H-indol-3-yl)acetates (3). The double bond of compounds 3 was reduced with zinc dust in boiling acetic acid to give 5, which upon methylation with methyl iodide in dry acetone and anhydrous potassium carbonate yielded the corresponding products 6. The structural assignments of the new compounds are based on the spectroscopic results.

Following Nature’s Footprint: Mimicking the High-Valent Heme-Oxo Mediated Indole Monooxygenation Reaction Landscape of Heme Enzymes

Pathways for direct conversion of indoles to oxindoles have accumulated considerable interest in recent years due to their significance in the clear comprehension of various pathogenic processes in humans and the multipotent therapeutic value of oxindole pharmacophores. Heme enzymes are predominantly responsible for this conversion in biology and are thought to proceed with a compound-I active oxidant. These heme-enzyme-mediated indole monooxygenation pathways are rapidly emerging therapeutic targets; however, a clear mechanistic understanding is still lacking. Additionally, such knowledge holds promise in the rational design of highly specific indole monooxygenation synthetic protocols that are also cost-effective and environmentally benign. We herein report the first examples of synthetic compound-I and activated compound-II species that can effectively monooxygenate a diverse array of indoles with varied electronic and steric properties to exclusively produce the corresponding 2-oxindole products in good to excellent yields. Rigorous kinetic, thermodynamic, and mechanistic interrogations clearly illustrate an initial rate-limiting epoxidation step that takes place between the heme oxidant and indole substrate, and the resulting indole epoxide intermediate undergoes rearrangement driven by a 2,3-hydride shift on indole ring to ultimately produce 2-oxindole. The complete elucidation of the indole monooxygenation mechanism of these synthetic heme models will help reveal crucial insights into analogous biological systems, directly reinforcing drug design attempts targeting those heme enzymes. Moreover, these bioinspired model compounds are promising candidates for the future development of better synthetic protocols for the selective, efficient, and sustainable generation of 2-oxindole motifs, which are already known for a plethora of pharmacological benefits.

Electrochemical Umpolung C-H Functionalization of Oxindoles

Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C-H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, environmentally benign conditions. Importantly, it enables the functionalization of these scaffolds through C-O, and by extension to C-C or even C-N bond formation.

Rapid Oxidation Indoles into 2-Oxindoles Mediated by PIFA in Combination with n-Bu4NCl ? H2O

We report the development of a rapid approach for directly converting indoles into 2-oxindoles promoted by HOCl formed in situ from the combination of (bis(trifluoroacetoxy) iodo)benzene (PIFA) and n-Bu4NCl ? H2O. The procedure is widely functional group tolerant and provides 2-oxindoles in up to 95% yield within 5 min. The potential applications of the developed methodology are demonstrated by the gram-scale preparation of 3-methyl-2-oxindole (11 a), the one-pot two-step syntheses of spiro-oxindoles 26 a and 26 b, and the formal synthesis of (-)-folicanthine (2). (Figure presented.).

Synthetic method of indoline-2-ketone compound and application thereof

The invention discloses a synthetic method of an indoline-2-ketone compound and an application thereof. The synthetic method comprises the following steps: enabling a nitrobenzaldehyde compound, alkali and phosphorus ylide to react, and preparing a 2-nitr

Preparation method of 3-substituted oxidized indole and derivative

The invention belongs to the technical field of organic chemistry and pharmaceutical chemistry and particularly relates to a method of preparing 3-substituted oxidized indole and a derivative. In themethod, with a 3-substituted indole derivative as a raw material and one or more of a tetrabutyl ammonium halide compound/sodium chloride/sodium iodide/potassium iodide as additives, and one or more of dichloromethane/1,2-dichloroethane/tetrahydrofurane/methylbenzene/1,4-dioxane/ethyl acetate/methanol are added as solvents; then one or more of [bis(trifluoroacetoxyl)iodine]benzene/iodosobenzene diacetate are added as oxidants in order to carry out a reaction with reaction temperature being controlled, thus producing the 3-substituted oxidized indole derivative. The method has gentle reaction conditions, simple operations, short reaction time and high yield, and is free of a metal catalyst and is environment-friendly.

Asymmetric organocatalytic α-amination of 2-oxindoles with bis(2,2,2-trichloroethyl)azo-dicarboxylate

An enantioselective electrophilic amination of 3-substituted-2-oxindoles is reported, using bis(2,2,2-trichloroethyl)azo-dicarboxylate and commercially available Cinchona alkaloid organocatalysts. The best results were obtained in the reaction of 3-aryl s

Bioreduction of the C=C double bond with Pseudomonas monteilii ZMU-T17: One approach to 3-monosubstituted oxindoles

An efficient whole cell-mediated bioreduction of 3-methylene-2-oxindoles has been developed, affording a range of 3-monosubstituted oxindoles in moderate to good yields (41-82%) with Pseudomonas monteilii ZMU-T17 as biocatalyst. Additionally, a possible reaction pathway for this bioreduction of C=C double bond was proposed.

Chemoselective reduction of isatin-derived electron-deficient alkenes using alkylphosphanes as reduction reagents

Under mild reaction conditions, the C=C double bond inisatin-derived electron-deficient alkenes has been exclusively reduced in the presence of alkylphosphanes and water to afford the corresponding reduction products in good to excellent yields. A plausib

Dimethyl malonate as a one-carbon source: A novel method of introducing carbon substituents onto aromatic nitro compounds

A number of carbon substituents possessing various functional groups could be introduced onto aromatic nitro compounds using dimethyl malonate as a one-carbon source and linker. Decarboxylation of both the ester groups originating from dimethyl malonate in this methodology is particularly significant.