113258-76-7Relevant academic research and scientific papers
Synthesis of spiro[pyrazolin-3,3′-oxindoles] and 3-arylcarbonylmethyl substituted ylideneoxindoles by 1,3-dipolar cycloadditions of 3-ylideneoxindoles and in-situ-generated α-diazoketones
Jiang, Shan,Guo, Hong-Mei,Yao, Sheng,Shi, De-Qing,Xiao, Wen-Jing
, p. 10433 - 10443 (2017)
An efficient 1,3-dipolar cycloaddition of 3-ylideneoxindoles with in-situ-generated α-diazoketones to potentially biological active spiro[pyrazolin-3,3′-oxindoles] 4 with excellent regioselectivity and diastereoselectivity and synthetically useful buildin
Synthesis of (E)-oxindolylidene acetate using tandem palladium-catalyzed Heck and alkoxycarbonylation reactions
Lin, Wei-Jen,Shia, Kak-Shan,Song, Jen-Shin,Wu, Ming-Hsien,Li, Wen-Tai
, p. 220 - 228 (2015)
Tandem reactions use consecutive reaction steps to efficiently synthesize compounds of high molecular complexity. This paper presents a tandem Pd-catalyzed Heck and alkoxycarbonylation reaction for the stereoselective synthesis of (E)-oxindolylidene acetates. The mechanism underlying the Pd-catalyzed tandem reaction involves the syn-carbopalladation of ynamides followed by alkoxycarbonylation with CO and alcohol. This method makes it possible to obtain the desired (E)-configuration of oxindolylidene acetates exclusively. We evaluated the scope of the reaction by applying optimal reaction conditions to the facile synthesis of a library of (E)-oxindolylidene acetates. The resulting (E)-oxindolylidene acetates exhibited potent anticancer activities against a variety of human cancer cell lines. The anticancer activities of some (E)-oxindolylidene acetates were even superior to those of known CDK inhibitors indirubin-3′-oxime and roscovitine.
When Ethyl Isocyanoacetate Meets Isatins: A 1,3-Dipolar/Inverse 1,3-Dipolar/Olefination Reaction for Access to 3-Ylideneoxindoles
Yuan, Wen-Kui,Cui, Tao,Liu, Wei,Wen, Li-Rong,Li, Ming
, p. 1513 - 1516 (2018)
A new CuI/1,10-phen-catalyzed reaction for the synthesis of 3-ylideneoxindoles from readily available isatins and ethyl isocyanoacetate, in which ethyl isocyanoacetate acts as a latent two-carbon donor like the Wittig reagent, is reported. A tandem procedure including 1,3-dipolar cycloaddition/inverse 1,3-dipolar ring opening/olefination allows the preparation of 3-ylideneoxindoles with broad functional group tolerance.
Lewis acid catalyzed unprecedented [3 + 2] cycloaddition yields 3,3′-pyrrolidinyldispirooxindoles containing four contiguous chiral stereocenters with two contiguous quaternary spirostereocenters
Suman, Koorathota,Srinu, Lanka,Thennarasu, Sathiah
, p. 3732 - 3735 (2014)
A Lewis acid catalyzed domino reaction cascades through azide-alkene cycloaddition, rearrangement, aziridine ring opening, and azomethine cycloaddition with a parent dipolarophile, resulting in 3,3′- pyrrolidinyldispirooxindoles containing four contiguous
An organocatalytic Michael-aldol cascade: Formal [3+2] annulation to construct enantioenriched spirocyclic oxindole derivatives
Duan, Shu-Wen,Li, Yang,Liu, Yi-Yin,Zou, You-Quan,Shi, De-Qing,Xiao, Wen-Jing
supporting information; experimental part, p. 5160 - 5162 (2012/06/16)
An efficient organocatalytic Michael-aldol cascade reaction for the asymmetric synthesis of spirocyclic oxindole derivatives fused with tetrahydrothiophenes has been developed through a formal [3+2] annulation strategy.
Synthesis of functionalized spiroaziridine-oxindoles from 3-ylideneoxindoles: an easy route to 3-(aminoalkyl)oxindoles
Ammetto,Gasperi,Lorerto, M. Antonietta,Migliorini,Palmarelli,Tardella, P. Antonio
scheme or table, p. 6189 - 6197 (2010/03/24)
Novel potentially bioactive spiroaziridine-oxindoles have been prepared by treatment of easily accessible 3-ylidene-oxindoles with N-{[(4-nitrophenyl) sulfonyl]oxy}carbamate (NsONHCO2Et) in the presence of CaO. These compounds gave new 3-(amino
A stereochemical investigation of the nucleophilic addition of methyl ethyl ketone to (E)-alkyloxindolylideneacetates
El-Samahy, Fatma A.
, p. 62 - 66 (2007/10/03)
The reaction of (E)-(2-oxo-1,2-dihydroindol-3-ylidene)acetic acid esters (1) with methyl ethyl ketone in the presence of morpholine as a catalyst gave 4-oxo-2-(2-oxo-2,3-dihydro-1H-indole-3-yl)hexanoic acid esters, a diastereomeric mixture of two isomers (2A and 2B). Using aluminium oxide as a catalyst for the above reaction led to the formation of 4-oxo-3-methyl-2-(2-oxo-2,3-dihydro-1H-indole-3-yl)-pentanoic acid esters as a mixture of three isomers 3A, 3B and 3C, which upon methylation with methyl iodide in acetone and in the presence of anhydrous potassium carbonate yield the corresponding methylated products. The structural assignments of the new compounds are based on their chemical and spectroscopic properties. The stereochemical structures of 5aA, 5bB and 5aC are identified by X-ray analysis.
