34219-51-7

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 7299-58-3 phenylpropiolyl chloride 
• 201230-82-2 carbon monoxide 
• 170956-92-0 N-methyl-2-(2-phenylethynyl)aniline 
• 1174751-04-2 diethyl (2-((2-bromophenyl)(methyl)amino)-2-oxoethyl)phosphonate 
• 100-52-7 benzaldehyde 
• 1174751-05-3 diethyl (2-((2-chlorophenyl)(methyl)amino)-2-oxoethyl)phosphonate 
• 34219-52-8 3-benzylidene-1-methyl-1,3-dihydroindol-2-one 
• 94298-51-8 N-methyl-N,3-diphenylprop-2-ynamide 
• 100-42-5 styrene 
• 121-69-7 N,N-dimethyl-aniline 
• 615-43-0 2-iodophenylamine 
• 3335-85-1 3-benzyl-1-methyl-1,3-dihydroindol-2-one 

Downstream Products

• 34219-52-8 3-benzylidene-1-methyl-1,3-dihydroindol-2-one 
• 4679-83-8 (E)-3-(diphenylmethylene)-1-methylindolin-2-one 
• 1416431-87-2 C₂₂H₁₅NO 
• 1259283-50-5 ethyl 1'-methyl-2'-oxo-5-phenylspiro[cyclopent[2]ene-1,3'-indoline]-2-carboxylate 
• 3335-85-1 3-benzyl-1-methyl-1,3-dihydroindol-2-one 

Relevant academic research and scientific papers

Synthesis of (E)-3-Alkylideneindolin-2-ones by an Iron-Catalyzed Aerobic Oxidative Condensation of Csp3–H Bonds of Oxindoles and Benzylamines

A novel synthetic route for the construction of (E)-3-alkylideneindolin-2-ones through iron-catalyzed aerobic oxidative condensation of oxindoles with benzylamines has been developed. This oxidative reaction involves a sequence of C–H activation, amine self-condensation, nucleophilic addition, and C–C double bond formation. The synthetic importance of this protocol has been demonstrated by preparing tyrosine kinase inhibitors, anticonvulsant and antitumor agents, and other valuable 3-alkylideneindolin-2-one derivatives. Key intermediates are isolated and a plausible mechanistic pathway for the reaction has been discussed.

Microwave-Assisted Domino Heck Cyclization and Phosphorylation: Synthesis of Phosphorus Containing Heterocycles

A domino [Pd]-catalyzed intramolecular Heck cyclization followed by intermolecular phosphorylation, for the construction of phosphorus containing heterocyclic compounds, is presented. Notably, the process is accelerated by microwave heating conditions and enabled the construction of C–C and C–P bonds in short reaction times.

Copper powder-catalyzed chelation-assisted cascade reaction of: O -chloroarylacetic acids with amines under solvent- and ligand-free conditions: Synthesis of oxindoles

An efficient method to construct oxindole scaffolds from o-chloroarylacetic acids/esters with amines has been explored. This cascade protocol involves the in situ generation of o-aminoarylacetic acid derivatives by the copper powder catalyzed and weak O-chelation assisted Ullmann amination of unactivated C-Cl bonds under air, and solvent-/ligand-free conditions followed by annulative N-acylation.

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.

Reductive coupling of isatins with ketones and aldehydes by low-valent titanium

The reductive coupling of isatins with ketones and aldehydes by Zn-TiCl4 in THF gave two- and four-electron reduced products, 3-hydoxy-3-(1-hydoxyalkyl)oxindoles and 3-alkylideneoxindoles, selectively by controlling the reaction conditions. Alt

Room-temperature palladium-catalyzed intramolecular oxidative aminocarbonylation of vinylic C(sp2)-H bonds with amines and CO

A new, mild route to access 3-methyleneindolin-2-ones is presented that proceeds through a room-temperature, palladium-catalyzed intramolecular oxidative aminocarbonylation of alkenes with amines and CO. This method represents a new aminocarbonylation str

Room-Temperature Palladium-Catalyzed Intramolecular Oxidative Aminocarbonylation of Vinylic C(sp2)-H Bonds with Amines and CO

A new, mild route to access 3-methyleneindolin-2-ones is presented that proceeds through a room-temperature, palladium-catalyzed intramolecular oxidative aminocarbonylation of alkenes with amines and CO. This method represents a new aminocarbonylation str

Palladium/copper-catalyzed oxidative C-H alkenylation/N-dealkylative carbonylation of tertiary anilines

C-H/C-N activation: The first palladium/copper-catalyzed aerobic oxidative C-H alkenylation/N-dealkylative carbonylation of tertiary anilines has been developed. Various functional groups were tolerated and acrylic ester could also be suitable substrates. This transformation provided efficient and straightforward synthesis of biologically active 3-methyleneindolin-2-one derivatives from cheap and simple substrates. Copyright

Oxindole synthesis by palladium-catalysed aromatic C-H alkenylation

A strategy involving palladium-catalysed aromatic C-H functionalisation/ intramolecular alkenylation provides a convenient and direct synthesis of 3-alkylideneoxindoles. In the presence of 5 mol% of PdCl2MeCN 2 and AgOCOCF3, a wide variety of N-cinnamoylanilines gave 3-alkylideneoxindoles in moderate to good yield. The Royal Society of Chemistry.

Tandem Horner-Wadsworth-Emmons/Heck procedures for the preparation of 3-alkenyl-oxindoles: The synthesis of Semaxanib and GW441756

A tandem sequence involving Horner-Wadsworth-Emmons (HWE) olefination followed by a palladium-catalysed intramolecular Heck reaction has been developed to provide rapid access to 3-alkenyl-oxindoles from α-halo-anilides. This one-pot microwave accelerated process proceeds with catalytic palladium(II) acetate or tetrakis(triphenylphosphine)palladium, and has been used to prepare a range of adducts derived from aromatic, heteroaromatic and aliphatic aldehydes. The procedures can be used to prepare N-unprotected oxindoles directly and the applicability of the process has been established by carrying out one-pot syntheses of Semaxanib, an angiogenesis signalling inhibitor, and GW441756, an aza-oxindole Trk A inhibitor.