3456-79-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenyl-oxindole is used as a building block for the synthesis of various pharmaceuticals and organic compounds, contributing to the development of new drugs and therapeutic agents.
Used in Medical Applications:
3-Phenyl-oxindole is used as a therapeutic agent for its potential biological activities, including anti-inflammatory, antibacterial, and antifungal properties, making it a promising candidate for treating various medical conditions.
Used in Coordination Chemistry:
3-Phenyl-oxindole is used as a ligand in coordination chemistry, playing a crucial role in the formation of metal complexes and contributing to the advancement of this field.
Used in Catalysis:
3-Phenyl-oxindole is used in catalysis, where it can act as a catalyst or a catalyst support, facilitating chemical reactions and improving their efficiency.

InChI:InChI=1/C14H11NO/c16-14-13(10-6-2-1-3-7-10)11-8-4-5-9-12(11)15-14/h1-9,13H,(H,15,16)

Upstream product

• 4410-33-7 N-phenyl-2-hydroxy-4-phenylacetamide 
• 129822-44-2 (2-Benzyl-phenyl)-carbamic acid tert-butyl ester 
• 1161949-53-6 methyl 2-oxo-3-phenylindoline-1-carboxylate 
• 120-72-9 indole 
• 591-50-4 iodobenzene 
• 28059-64-5 2-benzylaniline 
• 95-51-2 o-chloroaniline 
• 1555-80-2 phenylacetic anhydride 
• 59-48-3 2-oxoindole 
• 108-95-2 phenol 
• 7647-01-0 hydrogenchloride 
• 139018-14-7 3-hydroxy-3-phenyl-1,3-dihydro-indol-2-one 
• 7732-18-5 water 
• 64-19-7 acetic acid 

Downstream Products

• 88323-50-6 1,3-Bis-morpholin-4-ylmethyl-3-phenyl-1,3-dihydro-indol-2-one 
• 28864-76-8 1,1’,3,3’-tetrahydro-3,3’-diphenyl-2H,2’H-3,3’-biindole-2,2’-dione 
• 93315-79-8 1-acetyl-3-methyl-3-phenyl-indolin-2-one 
• 1161949-53-6 methyl 2-oxo-3-phenylindoline-1-carboxylate 
• 1185774-56-4 (S)-diisopropyl 1-(2-oxo-3-phenylindolin-3-yl)hydrazine-1,2-dicarboxylate 
• 1235862-78-8 C₂₂H₁₈N₂O₃ 
• 1355995-94-6 C₂₂H₁₆Cl₂N₂O₃ 
• 1355995-96-8 C₂₃H₁₇F₃N₂O₃ 
• 1403814-58-3 C₂₄H₁₅NO₃ 

Relevant academic research and scientific papers

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.).

Copper-Catalyzed Asymmetric Propargylic Alkylation with Oxindoles: Diastereo- A nd Enantioselective Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters

A copper-catalyzed asymmetric propargylic alkylation of propargylic acetates with 3-substituted oxindoles for the stereoselective construction of vicinal tertiary and all-carbon quaternary stereocenters in a 3,3-disubstituted oxindole skeleton has been realized. The reaction proceeded smoothly under the catalysis of Cu(MeCN)4PF6combined with a chiral tridentate ferrocenyl P,N,N ligand, leading to a broad range of optically active 3,3-disubstituted oxindoles in high yields and with excellent diastereo- A nd enantioselectivities.

Selective Insertion of Alkynes into C-C σ Bonds of Indolin-2-ones: Transition-Metal-Free Ring Expansion Reactions to Seven-Membered-Ring Benzolactams or Chromone Derivatives

An unprecedented ring expansion reaction of indolin-2-ones with alkynyl ketones under transition-metal-free conditions has been developed. Base-promoted selective cleavage of a C-C σ bond of the amide is the key in this process, which provides a straightf

Palladium-Catalyzed Allylation of Cyclopropyl Acetylenes with Oxindoles to Construct 1,3-Dienes

A novel palladium-catalyzed allylic alkylation of oxindoles with cyclopropyl acetylenes has been developed. Various 1,3-diene oxindole framework bearing a quaternary stereocenter at the C3 position were synthesized straightforwardly in good to excellent yields with high regio-, and stereoselectivities. The reaction exhibited high atom economy and good functional group tolerance.

Synthesis of α-Aryl Oxindoles by Friedel-Crafts Alkylation of Arenes

α-Aryl oxindoles are accessed from isatin via a two-step procedure involving a phospha-Brook rearrangement and a Friedel-Crafts alkylation in a one-pot procedure. The use of 1,1,1,3,3,3-hexafluoro-2-propanol as solvent significantly extended the reaction

Metal-free and regiospecific synthesis of 3-arylindoles

A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ri

A iron catalytic oxidation of indole synthesis of compounds 2 - indole ketone compounds (by machine translation)

The invention discloses an iron catalytic oxidation indoles of synthesis of compounds 2 - indole ketone compounds, included in the organic solvent, water or an organic solvent in the aqueous solution, the hydrogen of the silane as promoter, in under the a

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.

Organocatalytic stereoselective conjugate addition of 3-substituted oxindoles with in situ generated ortho-quinone methides

A novel method for the stereoselective conjugate addition of 3-substituted oxindoles to in situ generated o-QMs was described. This process was catalyzed efficiently by a cinchonidine-derived squaramide catalyst in oil-water phase, furnishing the corresponding 3,3-disubsituted oxindole derivatives in moderate to high yields (up to 98%) with high stereoselectivities (up to 95% ee, 15.4:1 dr). The utility of this reaction was also investigated by the gram-scale synthesis and derivatization of one of the products.