28864-73-5

Upstream product

• 39755-95-8 5-methoxyisatine 
• 100-58-3 phenylmagnesium bromide 
• 879124-26-2 (E)-4-methoxy-1-nitro-2-styrylbenzene 
• 15757-31-0 5-methoxy-3-phenyl-2-indolinone 

Downstream Products

• 1243153-67-4 C₁₅H₁₄N₂O₂ 
• 15757-31-0 5-methoxy-3-phenyl-2-indolinone 
• 923568-89-2 tert-butyl 5-methoxy-2-oxo-3-phenylindoline-1-carboxylate 
• 1040749-58-3 1-(t-butoxycarbonyl)-2-oxo-5-methoxy-3-phenylindolin-3-yl t-butyl carbonate 

Relevant academic research and scientific papers

Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles

tert-Butoxide unlocks new reactivity patterns embedded in nitroarenes. Exposure of nitrostilbenes to sodium tert-butoxide was found to produce N-hydroxyindoles at room temperature without an additive. Changing the counterion to potassium changed the reaction outcome to yield solely oxindoles through an unprecedented dioxygen-transfer reaction followed by a 1,2-phenyl migration. Mechanistic experiments established that these reactions proceed via radical intermediates and suggest that counterion coordination controls whether an oxindole or N-hydroxyindole product is formed.

Preparation method of 3-hydroxyl-2-indolone derivative in water phase

The invention relates to a synthesis method of a 3-hydroxyl-2-indolone derivative in a water phase. The method includes the steps: adding 3-replacement-2-indolone compound (1a), a compound as shown ina formula 2a, sodium dodecyl sulfate (SDS) and solvent water into an Schlenk reaction bottle; placing the reaction bottle into a position with atmosphere conditions of a certain temperature and air,and stirring and reacting mixture in the reaction bottle; monitoring reaction processes by a TLC (thin-layer chromatography) or GC (gas chromatography); performing post-processing to obtain a target product 3-hydroxyl-2-indolone derivative (I) until raw materials completely react.

Preparation method of 3-substituted-3-hydroxy-2-indolone compounds

The invention provides a green synthesis method for preparing 3-substituted-3-hydroxy-2-indolone compounds. In the method, 3-substituted-2-indolone compounds 1a are taken as raw materials, and 3-substituted-3-hydroxy-2-indolone compounds are prepared conveniently with excellent yield under promotion of room temperature and TEMPO and/or other analogue 2a. The preparation method is simple in processand efficient and low in cost.

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.

Enantioselective construction of tetrasubstituted stereogenic carbons through bronsted base catalyzed michael reactions: α′-hydroxy enones as key enoate equivalent

Catalytic and asymmetric Michael reactions constitute very powerful tools for the construction of new C-C bonds in synthesis, but most of the reports claiming high selectivity are limited to some specific combinations of nucleophile/electrophile compound types, and only few successful methods deal with the generation of all-carbon quaternary stereocenters. A contribution to solve this gap is presented here based on chiral bifunctional Bronsted base (BB) catalysis and the use of α′-oxy enones as enabling Michael acceptors with ambivalent H-bond acceptor/donor character, a yet unreported design element for bidentate enoate equivalents. It is found that the Michael addition of a range of enolizable carbonyl compounds that have previously demonstrated challenging (i.e., α-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azlactones) to α′-oxy enones can afford the corresponding tetrasubstituted carbon stereocenters in high diastereo- and enantioselectivity in the presence of standard BB catalysts. Experiments show that the α′-oxy ketone moiety plays a key role in the above realizations, as parallel reactions under identical conditions but using the parent α,β-unsaturated ketones or esters instead proceed sluggish and/or with poor stereoselectivity. A series of trivial chemical manipulations of the ketol moiety in adducts can produce the corresponding carboxy, aldehyde, and ketone compounds under very mild conditions, giving access to a variety of enantioenriched densely functionalized building blocks containing a fully substituted carbon stereocenter. A computational investigation to rationalize the mode of substrate activation and the reaction stereochemistry is also provided, and the proposed models are compared with related systems in the literature.

Palladium-catalyzed asymmetric allylic alkylation of 3-aryloxindoles with allylidene dipivalate: A useful enol pivalate product

Triple A: The catalytic asymmetric allylic alkylation (AAA) of 3-aryloxindoles with allylidene dipivalate is described. This reaction affords stable, synthetically useful enol pivalates in high yield and with excellent regio- and enantioselectivity. A broad range of substrates is tolerated, including unprotected and 3-heteroaryl nucleophiles. Copyright

A concise silylamine approach to 2-amino-3-hydroxy-indoles with potent in vivo antimalaria activity

The development of a concise strategy to access 2-amino-3-hydroxy-indoles, which are disclosed as novel antimalarials with potent in vivo activity, is reported. Starting from isatins the target compounds are synthesized in 2 steps and in good yields via oxoindole intermediates by employing tert- butyldimethylsilyl amine (TBDMSNH2) as previously unexplored ammonia equivalent.

Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles

(Chemical Equation Presented) Catalytic variant: Allyl silanes and silyl enol ethers 1 are good substrates for the catalytic highly enantioselective fluorodesilylation using a combination of a biscinchona alkaloid, N-fluorobenzenesulfonimide (NFSI), and base (see scheme). Pharmaceutically attractive 3-aryl-3-fluorooxindoles such as 3 can also be synthesized with high enantioselectivity.