13672-24-7Relevant academic research and scientific papers
Divergent Synthesis of Oxindolylidene Acetates and Spirooxindolopyrrolidones from Arynes
Pandya, Virat G.,Mhaske, Santosh B.
, p. 1483 - 1486 (2018)
A novel process for the preparation of various (E)-oxindolylidene acetates using arynes and carbamoylpropiolates has been developed. The utility of this protocol is also further extended to the one-pot synthesis of complex spirooxindolopyrrolidones. This method provides a milder and transition-metal-free access to both of the target scaffolds in moderate to good yields.
A Morita–Baylis–Hillman Pathway to Wittig Products: One-Pot Transformation of Nitroalkylideneoxindoles to Oxindolylidene-Carboxylates
Satham, Lakshminarayana,Sankara, Chenikkayala Siva,Namboothiri, Irishi N. N.
supporting information, p. 6903 - 6908 (2020/09/21)
An unusual Morita–Baylis–Hillman (MBH) type reactivity of isatin-derived nitroalkenes with activated carbonyl compounds has been demonstrated for the first time. The unexpected 3-alkylideneoxindole esters were formed in moderate to excellent yields with complete stereoselectivity (only E-isomer). The proposed mechanism based on control experiments involves a hybrid MBH–Wittig pathway.
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
supporting information, p. 1513 - 1516 (2018/03/23)
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.
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 (2018/05/31)
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
Construction of 1-pyrroline skeletons by Lewis acid-mediated conjugate addition of vinyl azides
Zhu, Xu,Chiba, Shunsuke
supporting information, p. 2473 - 2476 (2016/02/18)
Lewis acid-mediated conjugate addition of vinyl azides to electron-deficient alkenes led to the efficient construction of 1-pyrroline skeletons. The reactions of vinyl azides with 3-alkylidene-2-oxoindolines afford 3′,4′-dihydrospiro[indoline-3,2′-pyrrol]-2-ones in a diastereoselective fashion, whereas those with dimethyl 2-alkylidenemalonates provide 4,5-dihydro-3H-pyrroles.
An efficient one pot regioselective synthesis of a 3,3′-spiro-phosphonylpyrazole-oxindole framework via base mediated [1,3]-dipolar cycloaddition reaction of the Bestmann - Ohira reagent with methyleneindolinones
Shelke, Anil M.,Suryavanshi, Gurunath
, p. 8669 - 8675 (2015/08/24)
A one pot, highly regioselective synthesis of racemic 3,3′-spiro-phosphonylpyrazole-oxindole by 1,3-dipolar cycloaddition of an in situ generated anion of dialkyl 1-diazomethylphosphonate from the Bestmann-Ohira reagent (BOR) & methyleneindolinones has be
Photochemical aryl radical cyclizations to give (E)-3-ylideneoxindoles
Gurry, Michael,Allart-Simon, Ingrid,McArdle, Patrick,Grard, Stphane,Sapi, Janos,Aldabbagh, Fawaz
, p. 15891 - 15899 (2015/01/08)
(E)-3-Ylideneoxindoles are prepared in methanol in reasonable to good yields, as adducts of photochemical 5-exo-trig of aryl radicals, in contrast to previously reported analogous radical cyclizations initiated by tris(trimethylsilyl)silane and azo-initia
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
supporting information, p. 3732 - 3735 (2014/08/05)
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
Quinine as an organocatalytic dual activator for the diastereoselective synthesis of spiro-epoxyoxindoles
Chouhan, Mangilal,Pal, Anang,Sharma, Ratnesh,Nair, Vipin A.
, p. 7119 - 7123 (2013/12/04)
A highly efficient organocatalytic approach has been developed for the diastereoselective epoxidation of (E)-3-ylidene-indolin-2-one derivatives using readily available natural product quinine and urea-hydrogen peroxide (UHP) in DCM at 10 C to afford trans spiro-epoxyoxindoles which were further utilized to obtain β-hydroxy-α-amino esters by water mediated regioselective ring opening from the less hindered end with aniline derivatives, under sonication.
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.
