3478-78-2

Upstream product

• 59-48-3 2-oxoindole 
• 108-94-1 cyclohexanone 
• 108-93-0 cyclohexanol 
• 91-56-5 indole-2,3-dione 
• 19472-74-3 2-(2-bromophenyl)acetonitrile 
• 1393491-84-3 2-(2-bromophenyl)-2-cyclohexylideneacetonitrile 

Downstream Products

• 92250-13-0 3-cyclohexylindolin-2-one 

Relevant academic research and scientific papers

Potassium fluoride on alumina: Dry synthesis of 3-arylidene-1,3-dihydro- indol-2-one under microwave irradiation

Aldehydes (2) or ketones (4) were condensed with 1,3-dihydro-indol-2- one (1) in presence of potassium fluoride on alumina without solvent under focused microwave irradiation.

Enantioselective photochemical rearrangements of spirooxindole epoxides catalyzed by a chiral bifunctional xanthone

The title compounds were shown to undergo an enantioselective photochemical rearrangement to 3-acylindolin-2-ones (16-33% ee). A xanthone, which is tethered via an anellated oxazole to a chiral 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one scaffold, efficiently catalyzed this reaction at 366nm, presumably by triplet sensitization. The observed enantioselectivity can be explained by hydrogen bonding of the oxindole substrate and the putative 1,3-diradical intermediate to the lactam part of the catalyst. Although one substrate enantiomer is processed with minor preference over the other, it was shown that the reaction is not stereospecific. Rather, the main reason for the observed selectivity is the enantioselective migration step.

Direct regio-, diastereo-, and enantioselective vinylogous Michael addition of prochiral 3-alkylideneoxindoles to nitroolefins

3-Alkylidene-2-oxindoles represent a simple, yet enabling subfamily of indole alkaloids, and their ability to react as electron-poor acceptors has largely been investigated. In contrast, their utility as pronucleophilic synthons remains elusive. In this context, the present article describes the successful execution of the direct, organocatalytic asymmetric Michael addition of prochiral 3-alkylideneoxindoles to nitroolefins. A variety of γ-substituted alkylideneoxindoles carrying two stereocenters at both the γ- and δ-carbon sites was assembled with excellent stereoselectivity and without olefin isomerization or stereochemical ablation. Copyright

Asymmetric Synthesis of Spirooxindole δ-Lactones with Vicinal Tertiary and Quaternary Stereocenters via Regio-, Diastereo-, and Enantioselective Organocatalytic Vinylogous Aldol-cyclization Cascade Reaction

A highly region-, diastereo-, and enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of prochiral 3-akylidene oxindoles to isatins has been achieved by using bifuctional organocatalysts. A variety of enantioenriched spirooxindole δ-lactones with vicinal tertiary and quaternary stereocenters were generated in good to excellent yields with good to high diastereoselectivities and enantioselectivities. (Figure presented.).

Manganese-Catalyzed C(α)-Alkylation of Oxindoles with Secondary Alcohols via Borrowing Hydrogen

A general and efficient C(α)-alkylation of oxindoles with unactivated secondary alcohols as alkylating agents catalyzed by a newly developed NNN-Mn(II) complex is reported. Mechanistic studies illustrate that the importance of the NH moiety in the complex and M-L cooperation play very important roles during the catalytic transformation.

Visible light induced hydrodifluoromethylation of alkenes derived from oxindoles with (difluoromethyl)triphenylphosphonium bromide

A visible light induced hydrodifluoromethylation of alkenes derived from oxindoles with (difluoromethyl)triphenylphosphonium bromide was developed. This reaction delivers a series of previously unknown difluoromethylated oxindoles containing C–CF2H quaternary centers in moderate to excellent yields. The resulting CF2H-containing oxindoles are potentially useful in drug discovery.

Pd(0)-Catalyzed Chemoselective Deacylative Alkylations (DaA) of N-Acyl 2-Oxindoles: Total Syntheses of Pyrrolidino[2,3- b]indoline Alkaloids, (±)-Deoxyeseroline, and (±)-Esermethole

We report an efficient Pd(0)-catalyzed deacylative allylation of N-acyl 3-substituted 2-oxindoles via the coupling of in situ generated nucleophiles (3 and 4) with allyl electrophiles for the synthesis of a variety of 2-oxindoles with C3-quaternary centers. Gratifyingly, this alkylation process is found to be highly chemoselective in nature, where a C-C bond formation is completely predominant over a C-N bond formation. A variety of key intermediates were synthesized utilizing an aforementioned methodology.

An expedient synthesis of 3-alkylideneoxindoles by Ti(OiPr) 4/pyridine-mediated Knoevenagel condensation

3-Alkylideneoxindoles have been prepared in excellent yields from oxindole and carbonyl compounds via an in situ generated titanium enolate of oxindole. (Z)-3-Alkylideneoxindoles could be synthesized selectively as major products from unsymmetrical ketones.

Phosphine-catalyzed enantioselective γ-addition of 3-substituted oxindoles to 2,3-butadienoates and 2-butynoates: Use of prochiral nucleophiles

The first phosphine-catalyzed enantioselective γ-addition with prochiral nucleophiles and 2,3-butadienoates as the reaction partners has been developed. Both 3-alkyl- and 3-aryl-substituted oxindoles could be employed in this process, which is catalyzed by a chiral phosphine that is derived from an amino acid, thus affording oxindoles that bear an all-carbon quaternary center at the 3-position in high yields and excellent enantioselectivity. The synthetic value of these γ-addition products was demonstrated by the formal total synthesis of two natural products and by the preparation of biologically relevant molecules and structural scaffolds.

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