97004-65-4

Upstream product

• 15757-32-1 3-hydroxy-1-methyl-3-phenyl-1,3-dihydro-2H-indol-2-one 
• 100-66-3 methoxybenzene 
• 61-70-1 N-methyl-2-indolinone 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 3335-97-5 1-methyl-3-phenylindolin-2-one 
• 108-86-1 bromobenzene 
• 108-90-7 chlorobenzene 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 100-52-7 benzaldehyde 
• 71910-56-0 N-methyl-2-oxo-N,2-diphenylacetamide 
• 100-61-8 N-methylaniline 
• 4358-87-6 (RS)-methyl mandelate 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 86839-47-6 r-2-Ethoxy-t-3-hydroxy-2-(p-methoxyphenyl)-1-methyl-3-phenylindolin 

Relevant academic research and scientific papers

Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives

3-Aryloxindole derivatives were synthesized through a Friedel-Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc) 2. Wide varieties of diethyl phosphates derived from N -arylmandelamides were converted almost quantitatively into oxindoles. When N, N -dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.

Graphene-Oxide-Catalyzed Cross-Dehydrogenative Coupling of Oxindoles with Arenes and Thiophenols

Here, we explore the GO-catalyzed cross-dehydrogenative coupling of oxindoles with arenes and thiophenols for the rapid synthesis of 3-aryloxindoles and 3-sulfenylated oxindoles. Control experiments and small-molecule mimicking studies reveal that the acidic nature and quinone-type functionalities of GO are synergistically utilized for the coupling reaction. The reaction proceeds under simple and mild reaction conditions, exhibits good functional group tolerance, and can be easily scaled up to the gram level. (Figure presented.).

Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands

The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i -Pr-BI-DIME and Me 2 -BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd 2 (dba) 3 / i -Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me 2 -BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.

Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes

A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.

FeIII-Catalyzed Cross-Dehydrogenative Arylation (CDA) between Oxindoles and Arenes under an Air Atmosphere

An efficient FeIII-catalyzed cross-dehydrogenative arylation (CDA) of 3-substituted oxindoles with activated arenes under an air atmosphere was developed to provide 3,3′-disubstituted oxindoles in good yields.

Heterocyclic 8?-Systems, 16 - Elimination Reactions of 2-Alkoxy-3-hydroxyindolines

Thermolysis of 2-ethoxy-3-hydroxyindolines 1a - f affords oxindoles 3a - f as main products and the corresponding 3-indolinones 2a - f as by-products.The reaction course via indole 2,3-oxide intermediates is discussed.For this reason rearrangement reactio