19621-24-0Relevant academic research and scientific papers
Asymmetric Dieckmann Condensation towards Spirocyclic Oxindoles Catalyzed by Amino Acid-Derived Phosphonium Salts
Yu, Longhui,Liu, Jun,Wang, Hongyu,Xu, Lijun,Wu, Yufei,Zheng, Changwu,Zhao, Gang
supporting information, p. 302 - 306 (2021/11/18)
An asymmetric Dieckmann condensation towards spirocyclic oxindoles and aza-oxindoles catalyzed by amino acid-derived phosphonium salt has been developed, which expanded the applicability of asymmetric phosphonium salt catalysis in the production of 1,3-dicarbonyl compounds. This reaction is distinguished by its mild conditions (?20 °C), low catalyst loading (3–5 mol%), and broad substrate scope (25 examples). Control experiments revealed that both the catalyst‘s phosphonium skeleton and H-bonding site were required. Product transformations and a gram scale experiment were also carried out. (Figure presented.).
Regioselective synthesis of heteroaryl triflones by LDA (lithium diisopropylamide)-mediated anionic thia-Fries rearrangement
Xu, Xiu-Hua,Wang, Xin,Liu, Guo-Kai,Tokunaga, Etsuko,Shibata, Norio
supporting information; experimental part, p. 2544 - 2547 (2012/07/14)
Novel heteroaryl triflones including oxindole, pyrazolone, pyridine, and quinoline derivatives have been regioselectively synthesized by LDA-mediated thia-Fries rearrangement for the first time. These reactions are also the first examples of the application of anionic thia-Fries rearrangement in heteroaromatic compounds.
Orthogonal Pd- and Cu-based catalyst systems for C- and N-arylation of oxindoles
Altman, Ryan A.,Hyde, Alan M.,Huang, Xiaohua,Buchwald, Stephen L.
supporting information; scheme or table, p. 9613 - 9620 (2009/02/02)
In the cross-coupling reactions of unprotected oxindoles with aryl halides, Pd- and Cu-based catalyst systems displayed orthogonal chemoselectivity. A Pd-dialkylbiarylphosphine-based catalyst system chemoselectively arylated oxindole at the 3 position, while arylation occurred exclusively at the nitrogen using a Cu-diamine-based catalyst system. Computational examination of the relevant L1Pd(Ar)(oxindolate) and diamine-Cu(oxindolate) species was performed to gain mechanistic insight into the controlling features of the observed chemoselectivity.
A Novel Class of "GABAergic" Agents: 1-Aryl-3-(aminoalkylidene)oxindoles
Sarges, Reinhard,Howard, Harry R.,Koe, B. Kenneth,Weissman, Albert
, p. 437 - 444 (2007/10/02)
Antagonism of mercaptopropionic acid (MPA) induced convulsions, reflecting a GABAergic mechanism, was observed in a series of 1-aryl-3-(aminoalkylidene)oxindoles.Optimal MPA antagonism was associated with 3-halo, 3-alkyl, and/or 4-alkoxy substituents in the pendant aryl ring and with (dimethylamino)methylene, 1-(dimethylamino)ethylidene and N-methyl-2-pyrrolidinylidene side chains.The precise mechanism of action of these agents is unclear at this time; however, they are not GABA mimics and they do not affect GABA levels.Like other GABAergic agents, these compounds are potent enhancers of benzodiazepine binding and they antagonize cyclic GMP elevations induced by isoniazid.Compounds from this series may therefore have potential therapeutic utility as anticonvulsants or anxiolytics.
Heteroylidene indolone compounds
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, (2008/06/13)
Certain substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones are highly potent gabaergic agents, valuable in the treatment of individuals suffering from schizophrenia or reversing the side effects of a previously or concurrently administered neuroleptic agent; or in the treatment of epilepsy. A wider class of substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones, together with 1-phenyl-3-(2-pyrrolidinylidene)-2(1H,3H)-indolones, and homologs thereof, are valuable in the treatment of anxiety.
