79419-76-4

Upstream product

• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 100-39-0 benzyl bromide 
• 3335-85-1 3-benzyl-1-methyl-1,3-dihydroindol-2-one 
• 61-70-1 N-methyl-2-indolinone 
• 100-51-6 benzyl alcohol 
• 87100-28-5 pinacol benzylboronate 
• 1354971-54-2 (±)-3-acetyl-3-benzyl-1-methylindolin-2-one 
• 1410940-10-1 (±)-methyl 3-benzyl-1-methyl-2-oxoindoline-3-carboxylate 
• 84088-88-0 methyl 3-(N-methyl-N-phenylamino)-3-oxopropanoate 
• 102-92-1 Cinnamoyl chloride 
• 118670-85-2 (2E)-N-(2-iodophenyl)-3-phenylprop-2-enamide 
• 615-43-0 2-iodophenylamine 
• 122100-93-0 N-(2-iodophenyl)-N-methylcinnamamide 

Relevant academic research and scientific papers

Palladium-catalyzed allylation and deacylative allylation of 3-acetyl-2-oxindoles with allylic alcohols

The Pd-catalyzed allylation of 3-acetyl-2-oxindoles with allyl alcohol is performed using 3 mol% of Pd(dba)2, rac-BINAP and BINOL phosphoric acid as catalytic mixture. This procedure allows the in situ synthesis of 3-allyl-2-oxindole by adding

Nucleophilic addition of benzylboronates to activated ketones

A method has been developed for the addition of benzylboronic acid pinacol ester to activated ketones including trifluoromethyl ketones in good yields. The use of DABCO as an additive was found to enhance the rate and efficiency of this reaction. In react

Sustainable Alkylation of Unactivated Esters and Amides with Alcohols Enabled by Manganese Catalysis

The first example of manganese-catalyzed C-alkylation of the carboxylic acid derivatives is reported. The bench-stable homogeneous manganese complex enables the transformation of the renewable alcohol and carboxylic acid derivative feedstock to higher value esters and amides. The reaction operates via hydrogen autotransfer and ideally produces water as the only side product. Importantly, aliphatic-, benzylic-, and heterocyclic-containing alcohols can be used as alkylating reagents, eliminating the need for mutagenic alkyl halides.

Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids

We present an effective deacylative alkylation strategy for the construction of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position. A wide variety of products with quaternary centers could be accessed by employing simple Pd(0) catalysis under mild reaction conditions. Importantly, the same strategy works equally well for the dimeric 2-oxindole system, furnishing products with a vicinal quaternary center in favour of meso-isomer as the major product. Eventual application to the total syntheses of meso-chimonanthine and meso-folicanthine very well demonstrates the synthetic potential of this strategy.

Solvent-dependent Baylis-Hillman reactions for the synthesis of 3-benzyl-3-hydroxyoxindoles and benzo-δ-sultams

We have developed a solvent-dependent method for the preparation of novel benzo-δ-sultam and 3-benzyl-3-hydroxy-N-methyloxindole scaffolds. A variety of 3-(methoxy(phenyl)methyl)-1-methyl-1H-benzo-[c][1,2]thiazine 2,2-dioxides and 3-benzyl-3-hydroxy-1-methylindolin-2-ones were obtained in moderate to high yields via DBU-catalyzed Baylis-Hillman reaction of a number of (E)-N-(2-formylphenyl)-N-methyl-2-phenylethenesulfonamides in DMF and MeOH, respectively. The proof of the structures relies on analytical investigation and X-ray crystallography. Whereas reaction of (E)-N-(2-formylphenyl)-N-methyl-2- phenylethenesulfonamides in MeOH presumably proceeds through intramolecular Baylis-Hillman/dehydration, 3-hydroxy-N-methyloxindoles seem to have been generated via intramolecular Baylis-Hillman/1,3-H shift/oxidation/intramolecular cyclization tandem sequences in DMF.

An expedient synthesis of Oxindole dimers by direct oxidative dimerization of oxindoles

Oxindole dimers have been used as intermediates in the synthesis of various cyclotryptamine alkaloids. An efficient direct synthesis of oxindole dimers has been carried out from 3-substituted oxindoles via an oxidative dimerization using manganese(III) ac

Cp2ZrCl2-induced Reformatsky and Barbier reactions on isatins: An efficient synthesis of 3-substituted-3-hydroxyindolin-2-ones

A mild and rapid one-pot process for Reformatsky and Barbier reactions using a catalytic quantity of zirconocene dichloride (Cp2ZrCl 2) as a promoter and zinc as a terminal reductant at room temperature in dimethyl formamide was developed. The protocol has wide substrate suitability and afforded the desired 3-substituted-3-hydroxyindolin-2-ones from istains in good yields and short reaction time.

Copper(I) iodide-promoted hydroxylation onto the lithium or potassium enolate of lactones and lactams

After enolization of lactones (1a,b) and lactams (2a,b) with lithium or potassium hexamethyldisilazide in THF, each resultant enolate was treated with a solution prepared by mixing copper(I) iodide, pyridine, and tert-butyl hydroperoxide or N-methylmorpho

Cathodic reduction of N-(2-iodophenyl)-N-alkylcinnamides: A novel sequential electrochemical radical cyclisation and hydroxylation

In recent years, intramolecular aryl radical cyclisation has emerged as a useful route for the synthesis of benzannulated heterocycles and carbocycles. The aryl radicals are generated in situ from aryl halides (iodides or bromides) with tributylstannyl hydride-AIBN, SmI2, Co(I) or under photochemical conditions. The present work envisages the generation of aryl radicals by cathodic reduction of the carbon-iodine bond of N-(2-iodophenyl)-N-alkylcinnamides and their intramolecular cyclisation. The cathodic reduction of N-(2-iodophenyl)-N-alkyl-cinnamides under deaerated conditions in DMF gave 1-alkyl-3-benzylindolin-2-ones regioselectively and in the presence of oxygen yielded surprisingly 1-alkyl-3-hydroxy-3-benzylindolin-2-ones. Both these products were formed by a 5-exo-trig process in good yields. A mechanism for the formation of the products has been proposed through the use of cyclic voltammetry, coulometry and controlled-potential electrolysis as well as deuterium labelling.