34219-45-9

Upstream product

• 1174751-04-2 diethyl (2-((2-bromophenyl)(methyl)amino)-2-oxoethyl)phosphonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 637-69-4 4-Methoxystyrene 
• 201230-82-2 carbon monoxide 
• 121-69-7 N,N-dimethyl-aniline 
• 61-70-1 N-methyl-2-indolinone 
• 779335-39-6 [(methyl-phenyl-carbamoyl)-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-methyl]-phosphonic acid diethyl ester 
• 27687-42-9 [(methyl-phenyl-carbamoyl)-methyl]-phosphonic acid diethyl ester 
• 152302-96-0 (1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-phosphonic acid diethyl ester 

Downstream Products

• 1039396-21-8 (E)-3-((4-methoxyphenyl)(phenyl)methylene)-1-methylindolin-2-one 
• 1416431-94-1 (Z)-3-((4-methoxyphenyl)(phenyl)methylene)-1-methylindolin-2-one 

Relevant academic research and scientific papers

Ultrasound-assisted, ZnBr2-catalyzed regio-and stereoselective synthesis of novel 3,3′-dispiropyrrolidine bisoxindole derivatives via 1,3-dipolar cycloaddition reaction of an azomethine ylide

Ultrasound irradiation in presence of 20% ZnBr2 effectively promotes regio-and stereo-selective cycloaddition reaction of azomethine ylide with a series of (E)-3-benzylideneindolin-2-ones to afford 3,3′-dispiropyrrolidine bisoxindole derivatives in excellent yields in methanol at room temperature. The factors affecting the cycloaddition reaction, for example solvent, catalyst, ultrasonic irradiation, are examined in detail to find the mildest conditions and highest reaction yields. The structure and stereochemistry of cycloadducts were determined by spectroscopic data and confirmed by X-ray crystallographic analysis.

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

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.

One-pot homolytic aromatic substitutions/HWE olefinations under microwave conditions for the formation of a small oxindole library

(Chemical Equation Presented) An efficient one-pot sequence comprising a homolytic aromatic substitution followed by an ionic Horner Wadsworth-Emmons olefination for the preparation of a small library of α,β-unsaturated oxindoles is presented. Microwave-induced heating is used to conduct these reactions. The homolytic aromatic substitution is mediated by the persistent radical effect.