1174045-74-9

Upstream product

• 100-61-8 N-methylaniline 
• 2985-33-3 monoethyl methylmalonate 
• 59050-15-6 ethyl 3-(N-methyl-N-phenylamino)-3-oxopropionate 
• 74-88-4 methyl iodide 
• 1071-46-1 hydrogen ethyl malonate 

Downstream Products

• 67271-29-8 (±)-ethyl 1,3-dimethyl-2-oxoindoline-3-carboxylate 

Relevant academic research and scientific papers

Intramolecular Dehydrogenative Coupling Approach to 2-Oxindoles Using Fe(OAc)2/NaI/Na2S2O8

Oxindole units are common structures that are featuring in natural products and drugs. A novel method for synthesizing 2-oxindoles from 1,3-dicarbonyl compounds based on ferrous salt and iodide catalyst was described. Using Fe(OAc)2/NaI/Na2S2O8, various 2-alkyl-3-phenylamino-3-oxopropanoates, bearing fluoro, chloro, bromo, alkyl, alkoxy, trifluoromethyl, cyano etc. on the benzene ring were converted smoothly into 2-oxindoles.

Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C-H and sp3 C-H bonds

The synthesis of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudo benzylic position has been achieved via a 'transition-metal-free' intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon-carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of β-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for this reaction.

Substrate scope in the copper-mediated construction of bis-oxindoles via a double C-H/Ar-H coupling process

Abstract The synthesis of bis-oxindoles via the copper(II)-mediated double cyclisation of linear bis-anilides is described. Cu(OAc)2·H2O was identified as an efficient and inexpensive catalyst for this process. In contrast to previous methods, which rely on the synthesis of the central core from existing oxindole building blocks, this new approach focusses on concurrent formation of both oxindole rings from a simple linear precursor, allowing the formation of bis-oxindoles containing a diverse range of cyclic and acyclic linkers using a single synthetic method.

A Direct C-H/Ar-H Coupling Approach to Oxindoles, Thio-oxindoles, 3,4-Dihydro-1 H-quinolin-2-ones, and 1,2,3,4-Tetrahydroquinolines

A copper(II)-catalysed approach to oxindoles, thio-oxindoles, 3,4-dihydro-1H-quinolin-2-ones, and 1,2,3,4-tetrahydroquinolines via formal C-H, Ar-H coupling is described. In a new variant, copper(II) 2-ethylhexanoate has been identified as an inexpensive and efficient catalyst for this transformation, which utilises atmospheric oxygen as the re-oxidant. Copper(II) 2-ethylhexanoate: The synthesis of oxindoles, thio-oxindoles, 3,4-dihydro-1H-quinolin-2-ones, and 1,2,3,4-tetrahydroquinolines from linear precursors by direct C-H, Ar-H coupling by using a single copper catalyst is reported (see scheme; DIPEA=diisopropylethylamine, EWG=electron-withdrawing group). The cyclisations are simple to perform, run open to the air, are moisture insensitive, and use an inexpensive catalyst.

Copper-mediated construction of spirocyclic bis-oxindoles via a double C-H, Ar-H coupling process

A double C-H, Ar-H coupling process for the conversion of bis-anilides into spirocyclic bis-oxindoles, enabling the concomitant formation of two all-carbon quaternary centers at oxindole 3-positions in a diastereoselective manner, is described. The optimum cyclization conditions utilize stoichiometric Cu(OAc)2·H2O/KOtBu in DMF at 110 °C and have been applied to prepare a range of structurally diverse bis-spirooxindoles in fair to good yields (28-77%); the method has also been extended to prepare bis-oxindoles linked by a functionalized acyclic carbon chain.

DDQ-mediated direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious approach to the tetracyclic core of ergot alkaloids

An efficient route to 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position has been developed via a DDQ-mediated Intramolecular-Dehydrogenative-Coupling (IDC). The methodology involves a one-pot C-alkylation of β-N-arylamido esters (7) concomitant with dehydrogenative-coupling in the presence of stoichiometric amount of DDQ. A tentative mechanistic route has been proposed for the oxidative coupling. The methodology provides a two-step entry to the ergoline structure of ergot alkaloids.

Intramolecular dehydrogenative coupling of sp2 C-H and sp 3 C-H bonds: An expeditious route to 2-oxindoles

An intramolecular-dehydrogenative-coupling (IDC) using "transition- metal-free" oxidation conditions has been achieved to synthesize a variety of 2-oxindoles bearing an all-carbon quaternary stereogenic center at the benzylic position. The methodology involves a one-pot C-alkylation of β-N-arylamido esters (3, 6) with alkyl halides using potassium tert-butoxide concomitant with a dehydrogenative coupling. A radical-mediated pathway has been tentatively proposed for the oxidative process.