2525-35-1

Usage

General Description

1-Methyl-3-ethyloxindole is a chemical compound with the formula C11H11NO. It is a type of oxindole, which is a heterocyclic compound that contains a six-membered ring with a nitrogen atom and a ketone group. 1-Methyl-3-ethyloxindole is used as a key intermediate in the synthesis of various pharmaceutical compounds and natural products due to its versatile reactivity and ability to undergo different types of chemical transformations. It is also known for its potential biological activities, including anti-inflammatory and anti-cancer properties, making it an interesting target for research and drug development. Additionally, 1-Methyl-3-ethyloxindole has been found in certain plants and is known to contribute to the characteristic odor of these natural products.

InChI:InChI=1/C11H13NO/c1-3-8-9-6-4-5-7-10(9)12(2)11(8)13/h4-8H,3H2,1-2H3

Upstream product

• 116496-46-9 2-bromo-N-methyl-N-phenylbutanamide 
• 122100-95-2 (2E)-N-(2-iodophenyl)-N-methylbut-2-enamide 
• 102804-48-8 (E)-But-2-enoic acid (2-bromo-phenyl)-methyl-amide 
• 201230-82-2 carbon monoxide 
• 41652-73-7 N-Methyl-o-(prop-2-enyl)aniline 
• 74-88-4 methyl iodide 
• 7446-70-0 aluminium trichloride 
• 603-76-9 1-methylindole 
• 97-94-9 triethyl borane 
• 102804-44-4 (E)-N-(2-bromophenyl)but-2-enamide 
• 615-36-1 2-bromoaniline 
• 615-43-0 2-iodophenylamine 
• 918334-77-7 (2E)-N-(2-iodophenyl)but-2-enamide 
• 71-23-8 propan-1-ol 

Downstream Products

• 121670-69-7 Toluene-4-sulfonic acid 2-(3-ethyl-1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-ethyl ester 

Relevant academic research and scientific papers

Deoxygenative α-alkylation and α-arylation of 1,2-dicarbonyls

Construction of C-C bonds at the α-carbon is a challenging but synthetically indispensable approach to α-branched carbonyl motifs that are widely represented among drugs, natural products, and synthetic intermediates. Here, we describe a simple approach to generation of boron enolates in the absence of strong bases that allows for introduction of both α-alkyl and α-aryl groups in a reaction of readily accessible 1,2-dicarbonyls and organoboranes. Obviation of unselective, strongly basic and nucleophilic reagents permits carrying out the reaction in the presence of electrophiles that intercept the intermediate boron enolates, resulting in two new α-C-C bonds in a tricomponent process. This journal is

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.

Visible light induced radical cyclization of o-iodophenylacrylamides: A concise synthesis of indolin-2-one

A [Ir(ppy)2(dtb-bpy)]PF6-catalyzed intramolecular radical cyclization of o-iodophenylacrylamides affording indolin-2-ones in moderate to excellent yields via 5-exo-trig radical cyclization under visible light is presented. This method provides new access to the synthesis of indolin-2-ones under mild reaction conditions. This journal is

Rhenium-catalyzed acceptorless dehydrogenative coupling via dual activation of alcohols and carbonyl compounds

The rhenium hetaphydride complex was found to be a versatile, homogeneous catalyst for dehydrogenative functionalization of alcohol. The dehydrogenative C-C coupling of alcohols and carbonyl compounds was carried out in the absence of base and hydrogen acceptors to afford a series of α,β-unsaturated carbonyl compounds. A possible dual activation pathway was proposed by mechanistic investigations.

A tandem radical cyclization approach to 3-(2-oxopyrrolidin-3-yl)indolin-2-ones, potential intermediates toward complex indole-heterocycles

A series of substituted 3-(2-oxopyrrolidin-3-yl)indolin-2-one derivatives have been synthesized by tris(trimethylsilyl)silane (TTMSS) induced tandem radical cyclization as key step.

A palladium-catalyzed tandem cyclization-cross-coupling reaction using indolylborate as a transfer agent

Investigation of the palladium-catalyzed tandem cyclization-cross-coupling reaction using indolylborate (2) as a transfer agent has been carried out. Furthermore, the cross-coupling reaction performed under carbon monoxide led to the generation of indolyl

Regioselective palladium(II)-catalyzed synthesis of five- or seven-membered ring lactones and five-, six- or seven-membered ring lactams by cyclocarbonylation methodology

2-Allylphenols react with carbon monoxide and hydrogen in the presence of catalytic quantities of a cationic palladium(II) complex [(PCy3)2Pd(H)(H2O)]+BF4- or palladium acetate and 1,4-bis(diphenylpho

Cobalt(II) Chloride-Grignard Reagent: an Alternative to Tin Hydride in Aryl Radical Cyclisations

Reaction of N-methyl,N-acryloyl-2-haloanilines with anhydrous cobalt(II) chloride and a Grignard reagent leads to formation of indol-2(3H)-ones via a reductive aryl radical cyclisation.

SYNTHESIS OF OXINDOLES BY RADICAL CYCLISATION

Oxindoles are readily synthesised by intramolecular addition of aryl radicals to the α-position of α,β-unsaturated N-alkylamides.

An Efficient Synthesis of Spiro via Radical Cyclisation

Treatment of the o-bromo-N-acryloylanilides (4) with tri-n-butylstannane leads to the formation of 3-substituted- and 3,3-disubstituted-2-oxindoles (5) in high yield.