111500-91-5Relevant academic research and scientific papers
Rhodium-catalyzed addition of arylboronic acids to isatins: An entry to diversity in 3-aryl-3-hydroxyoxindoles
Toullec, Patrick Y.,Jagt, Richard B. C.,De Vries, Johannes G.,Feringa, Ben L.,Minnaard, Adriaan J.
, p. 2715 - 2718 (2006)
A general method for the catalytic 1,2-addition of aryl and alkenyl boronic acids to isatins is described using a rhodium(I)/triphenylphosphite catalyst. The application of this transformation allows the synthesis of a variety of 3-aryl-3-hydroxyoxindole
Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones
Vayer, Marie,Pastor, Miryam,Kofink, Christiane,Maulide, Nuno
supporting information, p. 27 - 32 (2022/01/15)
We report an unexpected rearrangement of 3-hydroxyoxindoles into benzoxazinones using electrochemistry. Our reaction employs mild and environmentally friendly conditions, and the benzoxazinone products are obtained in moderate to excellent yields. Mechanistic experiments suggest that a peroxide intermediate is likely involved.
Synthetic Studies toward 1,2,3,3a,4,8b-Hexahydropyrrolo[3,2-b]indole Core. Unusual Fragmentation with 1,2-Aryl Shift
Aksenov, Alexander V.,Aksenov, Dmitrii A.,Aksenov, Nicolai A.,Aksenova, Anna A.,Aleksandrova, Elena V.,Nobi, Mezvah A.,Rubin, Michael
, p. 1434 - 1444 (2022/01/27)
Base-assisted transformations of 2-(3-oxoindolin-2-yl)acetonitriles were investigated. Unexpectedly, attempted reactions of substrates possessing nonprotected nitrogen atoms were accompanied by unusual extrusions of 2-arylacetonitriles, followed by a 1,2-aryl shift to afford 3-hydroxyindolin-2-ones. On the other hand, the reactions for N-alkyl derivatives of oxoindolines took the expected route by only providing 1,2,3,3a,4,8b-hexahydropyrrolo[3,2-b]indoles.
Electrochemical Umpolung C-H Functionalization of Oxindoles
Maulide, Nuno,Pastor, Miryam,Vayer, Marie,Weinstabl, Harald
supporting information, (2022/01/12)
Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C-H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, environmentally benign conditions. Importantly, it enables the functionalization of these scaffolds through C-O, and by extension to C-C or even C-N bond formation.
Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles
Fujii, Kazuki,Mandai, Hiroki,Mitsudo, Koichi,Shiomoto, Ryuhei,Suga, Seiji
supporting information, p. 1169 - 1174 (2021/01/13)
We developed an efficient acylative kinetic resolution of 3-hydroxy-3-substituted 2-oxindoles by a chiral DMAP derivative having a 1,1′-binaphthyl with two tert-alcohols units. A wide range of 3-hydroxy-3-substituted oxindoles having various functional groups were efficiently resolved (14 examples, up to s = 60) in the presence of 1 mol % of catalyst within 3-9 h. Multigram-scale reactions (10 g) also proceeded with a high s-factor (s = 43) within 5 h.
Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles
Driver, Tom G.,Sung, Siyoung,Wink, Donald J.,Zadrozny, Joseph M.,Zhao, Yingwei,Zhu, Haoran
, p. 19207 - 19213 (2021/08/09)
tert-Butoxide unlocks new reactivity patterns embedded in nitroarenes. Exposure of nitrostilbenes to sodium tert-butoxide was found to produce N-hydroxyindoles at room temperature without an additive. Changing the counterion to potassium changed the reaction outcome to yield solely oxindoles through an unprecedented dioxygen-transfer reaction followed by a 1,2-phenyl migration. Mechanistic experiments established that these reactions proceed via radical intermediates and suggest that counterion coordination controls whether an oxindole or N-hydroxyindole product is formed.
One-pot synthesis of 3-hydroxy-2-oxindoles: Via acyloin rearrangements of 2-hydroxy-indolin-3-ones generated in situ from 2-alkynyl arylazides
Zhou, Zhiqiang,Xu, Yao,Zhu, Boyu,Li, Ping,Hu, Guiwen,Yang, Fan,Xu, Shijie,Zhang, Xiaoxiang
supporting information, p. 20303 - 20307 (2020/12/21)
A novel one-pot method to prepare 3-hydroxy-2-oxindoles via acyloin rearrangements of 2-hydroxy-indolin-3-ones generated in situ from 2-alkynyl arylazides has been described. The reaction was accomplished to afford a variety of 3-hydroxy-2-oxindole derivatives in moderate to good yields under mild conditions. This journal is
Asymmetric organocatalytic α-amination of 2-oxindoles with bis(2,2,2-trichloroethyl)azo-dicarboxylate
Bondanza, Mattia,Pescitelli, Gennaro,Mandoli, Alessandro
supporting information, p. 2590 - 2594 (2018/05/29)
An enantioselective electrophilic amination of 3-substituted-2-oxindoles is reported, using bis(2,2,2-trichloroethyl)azo-dicarboxylate and commercially available Cinchona alkaloid organocatalysts. The best results were obtained in the reaction of 3-aryl s
Organocatalytic stereoselective conjugate addition of 3-substituted oxindoles with in situ generated ortho-quinone methides
Liang, Weihong,Yin, Wenhao,Wang, Tingzhong,Qiu, Fayang G.,Zhao, Junling
supporting information, p. 1742 - 1747 (2018/04/02)
A novel method for the stereoselective conjugate addition of 3-substituted oxindoles to in situ generated o-QMs was described. This process was catalyzed efficiently by a cinchonidine-derived squaramide catalyst in oil-water phase, furnishing the corresponding 3,3-disubsituted oxindole derivatives in moderate to high yields (up to 98%) with high stereoselectivities (up to 95% ee, 15.4:1 dr). The utility of this reaction was also investigated by the gram-scale synthesis and derivatization of one of the products.
Pd(0)-Catalyzed Chemoselective Deacylative Alkylations (DaA) of N-Acyl 2-Oxindoles: Total Syntheses of Pyrrolidino[2,3- b]indoline Alkaloids, (±)-Deoxyeseroline, and (±)-Esermethole
Kumar, Nivesh,Gavit, Vipin R.,Maity, Arindam,Bisai, Alakesh
, p. 10709 - 10735 (2018/09/29)
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.
