- Divergent Synthesis of Oxindolylidene Acetates and Spirooxindolopyrrolidones from Arynes
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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.
- Pandya, Virat G.,Mhaske, Santosh B.
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- A Morita–Baylis–Hillman Pathway to Wittig Products: One-Pot Transformation of Nitroalkylideneoxindoles to Oxindolylidene-Carboxylates
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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.
- Satham, Lakshminarayana,Sankara, Chenikkayala Siva,Namboothiri, Irishi N. N.
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supporting information
p. 6903 - 6908
(2020/09/21)
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- When Ethyl Isocyanoacetate Meets Isatins: A 1,3-Dipolar/Inverse 1,3-Dipolar/Olefination Reaction for Access to 3-Ylideneoxindoles
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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.
- Yuan, Wen-Kui,Cui, Tao,Liu, Wei,Wen, Li-Rong,Li, Ming
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supporting information
p. 1513 - 1516
(2018/03/23)
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- 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
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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
- Jiang, Shan,Guo, Hong-Mei,Yao, Sheng,Shi, De-Qing,Xiao, Wen-Jing
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p. 10433 - 10443
(2018/05/31)
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- Construction of 1-pyrroline skeletons by Lewis acid-mediated conjugate addition of vinyl azides
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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.
- Zhu, Xu,Chiba, Shunsuke
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supporting information
p. 2473 - 2476
(2016/02/18)
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- 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
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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
- Shelke, Anil M.,Suryavanshi, Gurunath
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p. 8669 - 8675
(2015/08/24)
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- Photochemical aryl radical cyclizations to give (E)-3-ylideneoxindoles
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(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
- Gurry, Michael,Allart-Simon, Ingrid,McArdle, Patrick,Grard, Stphane,Sapi, Janos,Aldabbagh, Fawaz
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p. 15891 - 15899
(2015/01/08)
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- Lewis acid catalyzed unprecedented [3 + 2] cycloaddition yields 3,3′-pyrrolidinyldispirooxindoles containing four contiguous chiral stereocenters with two contiguous quaternary spirostereocenters
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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
- Suman, Koorathota,Srinu, Lanka,Thennarasu, Sathiah
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supporting information
p. 3732 - 3735
(2014/08/05)
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- Quinine as an organocatalytic dual activator for the diastereoselective synthesis of spiro-epoxyoxindoles
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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.
- Chouhan, Mangilal,Pal, Anang,Sharma, Ratnesh,Nair, Vipin A.
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p. 7119 - 7123
(2013/12/04)
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- An organocatalytic Michael-aldol cascade: Formal [3+2] annulation to construct enantioenriched spirocyclic oxindole derivatives
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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.
- Duan, Shu-Wen,Li, Yang,Liu, Yi-Yin,Zou, You-Quan,Shi, De-Qing,Xiao, Wen-Jing
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supporting information; experimental part
p. 5160 - 5162
(2012/06/16)
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- Noncovalent organocatalysis: A powerful tool for the nucleophilic epoxidation of α-ylideneoxindoles
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A novel asymmetric nucleophilic epoxidation for α-ylideneoxindole esters has been successfully devised, resulting in enantioenriched spiro compounds with two new contiguous stereocenters. The employed (S)-α,α-diphenylprolinol functions as a bifunctional c
- Palumbo, Chiara,Mazzeo, Giuseppe,Mazziotta, Andrea,Gambacorta, Augusto,Loreto, M. Antonietta,Migliorini, Antonella,Superchi, Stefano,Tofani, Daniela,Gasperi, Tecla
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supporting information; experimental part
p. 6248 - 6251
(2012/01/15)
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- Chemoselective reduction of isatin-derived electron-deficient alkenes using alkylphosphanes as reduction reagents
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Under mild reaction conditions, the C=C double bond inisatin-derived electron-deficient alkenes has been exclusively reduced in the presence of alkylphosphanes and water to afford the corresponding reduction products in good to excellent yields. A plausib
- Cao, Shu-Hua,Zhang, Xiu-Chun,Wei, Yin,Shi, Min
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p. 2668 - 2672
(2011/06/25)
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- INDOLINONE COMPOUND
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[Problems] A compound, which is useful as an active ingredient for a pharmaceutical composition, for example a pharmaceutical composition for treating constipation-type irritable bowel syndrome, atonic constipation and/or functional gastrointestinal disorder, is provided. [Means for Solution] The present inventors have extensively studied compounds having TRPA1 channel activation activity, and confirmed that an indolinone compound has a TRPA1 channel activation activity, and thus completed the present invention. The indolinone compound of the present invention has a TRPA1 channel activation activity and can be used as an active ingredient of a pharmaceutical composition for preventing and/or treating constipation-type irritable bowel syndrome, atonic constipation and/or functional gastrointestinal disorder or the like.
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Page/Page column 25
(2010/12/30)
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