- Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of 3-substituted oxindoles
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Quinidine derivative (QD)2PYR was found to catalyze the asymmetric direct amination of unprotected prochiral 3-oxindole with DIAD to construct quaternary stereocenters at the C3 position with excellent enantioselectivity.
- Qian, Zi-Qing,Zhou, Feng,Du, Tai-Ping,Wang, Bo-Lun,Ding, Miao,Zhao, Xiao-Li,Zhou, Jian
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- C-3 alkylation of oxindole with alcohols by Pt/CeO2 catalyst in additive-free conditions
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In a series of transition metal-loaded CeO2 catalysts and Pt-loaded catalysts on various supports, Pt-loaded CeO2 shows the highest activity for the selective C-3 alkylation of oxindole with octanol. The catalyst is effective for alkylation of oxindole and N-substituted oxindole with a series of substituted benzyl, linear, hetero-aryl alcohols under additive-free conditions and is recyclable. Our results demonstrate the first additive-free catalytic system for this reaction. Mechanistic studies show that this system is driven by the borrowing-hydrogen pathway. Structure-activity relationship studies show that co-presence of surface Pt0 species on Pt metal clusters and basic support is indispensable for this catalytic system. This journal is the Partner Organisations 2014.
- Chaudhari, Chandan,Siddiki, S. M. A. Hakim,Kon, Kenichi,Tomita, Atsuko,Tai, Yutaka,Shimizu, Ken-Ichi
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p. 1064 - 1069
(2014/04/03)
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- A Facile Method for the Synthesis of 3-Alkyloxindole
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Benzylamine in combination with acetic acid was identified as a powerful catalyst for the condensation of oxindole with aldehydes, acetone or cyclic ketones. A variety of 3-alkyloxindoles could be readily prepared in 10 mmol scale via the sequential benzylamine acetate catalyzed condensation of oxindoles with aldehydes (or ketones) and conjugate reduction by NaBH4.
- Du, Tai-Ping,Zhu, Gang-Guo,Zhou, Jian
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experimental part
p. 225 - 232
(2012/07/14)
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- Iridium catalysed C-3 alkylation of oxindole with alcohols under solvent free thermal or microwave conditions
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Ir-catalysed alkylation of oxindole and N-methyl oxindole with a range of substituted benzyl and heteroaryl alcohols under solvent free thermal or microwave conditions afforded the corresponding C-3-monoalkylated products in high to excellent yield.
- Grigg, Ronald,Whitney, Simon,Sridharan, Visuvanathar,Keep, Ann,Derrick, Andrew
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experimental part
p. 4375 - 4383
(2009/10/17)
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- (Phenylpiperazinyl-butyl)oxindoles as selective 5-HT7 receptor antagonists
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A series of potent 5-hydroxytryptamine7 (5-HT7) ligands has been synthesized that contain a 1,3-dihydro2H-indol-2-one (oxindole) skeleton. The binding of these compounds to the 5-HT7 and 5-HT 1A receptors was measured. Despite the structural similarity of these two serotonin receptor subtypes, several derivatives exhibited a high selectivity to the 5-HT7 receptor. According to the structure-activity relationship observations, compounds unsubstituted at the oxindole nitrogen atom and containing a tetramethylene spacer between the oxindole skeleton and the basic nitrogen atom are the most potent ligands. Concerning the basic group, besides the moieties of the 4-phenylpiperazine type, halophenyl-1,2,3,6-tetrahydropyridines also proved to be 5-HT7 receptor-ligands. Because of halogen substitution on the aromatic rings, good metabolic stability could be achieved. A representative of the family, 3-{4-[4-(4-chlorophenyl)-piperazin-1-yl]-butyl}-3-ethyl-6-fluoro-1, 3-dihydro-2H-indol-2-one (9e′) exhibited selective 5-HT7 antagonist activity (K: = 0.79 nM). The in vivo pharmacological potencies of these 5-HT7 receptor-ligands were estimated by the conflict drinking (Vogel) and the light-dark anxiolytic tests.
- Volk, Balázs,Barkóczy, József,Hegedus, Endre,Udvari, Szaboles,Gacsályi, István,Mezei, Tibor,Pallagi, Katalin,Kompagne, Hajnalka,Lévay, Gy?rgy,Egyed, András,Hársing Jr., Lásló G.,Spedding, Michael,Simig, Gyula
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p. 2522 - 2532
(2008/12/23)
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- Unexpected 7-methylation of oxindoles
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A unique, regioselective 7-methylation reaction has been discovered during the reductive 3-alkylation of isatin with i-BuOH at 230°C, in the presence of Raney nickel, under hydrogen atmosphere. Based on this observation, a synthetic method has been elaborated for the preparation of 3-alkyl-7-methyloxindoles.
- Volk, Balazs,Kapiller-Dezsofi, Rita,Simig, Gyula
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p. 539 - 547
(2007/10/03)
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- New One-Pot Synthesis of 3-Alkyl- and 3-(ω-Hydroxyalkyl)oxindoles from Isatins
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A new and efficient one-pot procedure has been developed for the synthesis of 3-alkyl- and 3-(ω-hydroxyalkyl)oxindoles from isatins by treatment with alcohols and diols in the presence of Raney nickel, under hydrogen atmosphere. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Volk, Balazs,Simig, Gyula
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p. 3991 - 3996
(2007/10/03)
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- Raney nickel-induced 3-alkylation of oxindole with alcohols and diols
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New reaction conditions are described, which turn Wenkert's synthesis of 3-alkyloxindoles (Raney nickel-induced alkylation of oxindole with alcohols) into a reproducible and highly efficient synthetic tool. The method is also extended to the preparation o
- Volk, Balázs,Mezei, Tibor,Simig, Gyula
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p. 595 - 597
(2007/10/03)
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