- A New Radical Based Synthesis of Lactams and Indolones from Dithiocarbonates (Xanthates).
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N,N-disubstituted α-(xanthyl)-acetamides with an olefin on one of the substituents undergo cyclisation to a lactam by a radical chain reaction involving transfer of the xanthate group; anilides lead to the corresponding indolones.
- Axon, Jonathan,Boiteau, Laurent,Boivin, Jean,Forbes, Judith E.,Zard, Samir Z.
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Read Online
- Copper(I) reactions in N-heterocycle synthesis: Efficient preparation of substituted pyrrolidinones
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Reaction of halo-enamides with copper(I) chloride in boiling toluene has been shown to produce unsaturated pyrrolidinones in excellent yield (81-94%). Both di- and trichloroamide precursors can be used to form dienes via an initial 5-endo-trig radical cyc
- Davies, David T.,Kapur, Neha,Parsons, Andrew F.
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Read Online
- New cell cycle checkpoint pathways regulators with 2-Oxo-indoline scaffold as potential anticancer agents: Design, synthesis, biological activities and in silico studies
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3-Arylidene-2-oxo-indoline derivatives are at the heart of a wide range of clinically, medicinally and biologically important compounds among the 2-oxo-indolines. A number of 3-arylidene-2-oxo-indolines have been approved for clinical application. Accordi
- Abd El-wahab, Hend A.A.,Mansour, Hany S.,Ali, Ahmed M.,El-Awady, Raafat,Aboul-Fadl, Tarek
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- Heterogeneous palladium-catalysed intramolecular C(sp3)[sbnd]H α-arylation for the green synthesis of oxindoles
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Herein, we present our results on the development of a waste-minimized protocol for the synthesis of oxindoles using cyclopentyl methyl ether (CPME) as a safe and green reaction medium and palladium on carbon (Pd/C) as a reusable catalyst. This protocol is efficiently applied to a variety of substrates affording products with excellent yields, minimal metal contamination and minimum waste production. The catalyst was recovered and reused for four consecutive runs without any apparent loss of efficiency. Moreover, products were isolated by simple precipitation from heptane with no need for chromatographic separations, and both CPME and heptane were recovered. Waste-minimization is reflected by the low E-factor calculated for the presented protocol.
- Anastasiou, Ioannis,Chen, Shaomin,Ferlin, Francesco,Gu, Yanglong,Liu, Ping,Minio, Francesco,Salameh, Nihad,Santoro, Stefano,Vaccaro, Luigi
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- A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids
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A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.
- Huang, Tiao,Kong, Dulin,Li, Yue,Liu, Li,Wu, Mingshu
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p. 2321 - 2328
(2021/09/22)
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- 3-Carboxamide oxindoles as 1,3-C,N-bisnucleophiles for the highly diastereoselective synthesis of CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atom
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A simple and efficient strategy has been established for the synthesis of δ-lactam fused oxindoles via the Michael/N-hemiketalization cascade reaction of 3-carboxamide oxindoles and α,β-unsaturated trifluoromethyl ketones. A wide range of structurally novel CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atoms were obtained in moderate to good yields with excellent diastereoselectivities under mild conditions. This work represents the first example of a systematic study of 3-carboxamide oxindoles as 1,3-C,N bisnucleophiles.
- Zhao, Hongcai,Zhang, Zhengbing,Lu, Wenhua,Han, Pan,Wang, Wei,Jing, Linhai
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- Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide
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Oxidative rearrangement of indoles is an important transformation to yield 2-oxindoles and spirooxindoles, which are present in many pharmaceutical agents and bioactive natural products. Previous oxidation methods show either broad applicability or greenness but rarely achieve both. Reported is the discovery of Fenton chemistry-enabled green catalytic oxidative rearrangement of indoles, which has wide substrate scope (42 examples) and greenness (water as the only stoichiometric byproduct) at the same time. Detailed mechanistic studies revealed that the Fenton chemistry generated hydroxyl radicals that further oxidize bromide to reactive brominating species (RBS: bromine or hypobromous acid). Thisin situgenerated RBS is the real catalyst for the oxidative rearrangement. Importantly, the RBS is generated under neutral conditions, which addresses a long-lasting problem of many haloperoxidase mimics that require a strong acid for the oxidation of bromide with hydrogen peroxide. It is expected that this new catalytic Fenton-halide system will find wide applications in organic synthesis.
- Zhao, Guodong,Liang, Lixin,Wang, Eryu,Lou, Shaoyan,Qi, Rui,Tong, Rongbiao
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supporting information
p. 2300 - 2307
(2021/04/12)
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- Green method for preparing oxindole derivative
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The invention relates to the technical field of green organic synthesis, and provides a green method for preparing oxindole derivatives, which comprises the following steps: taking indole compounds with different functional groups as raw materials, under the conditions of room temperature, opening and neutral, adopting MBrx (M is Fe,Fe,Ce and the like) as a catalyst with X equal to 2 or 3, and adopting hydrogen peroxide as a sole oxidant to generate active bromine (RBS) in situ, and catalytically synthesizing the oxindole derivative. According to the method disclosed by the invention, MBrx (such as FeBr2, CeBr3 and the like) is used as the catalyst, so that an expensive or complex catalyst is avoided, and the method is green, environment-friendly, safe, simple, efficient, mild in reaction condition and wide in substrate application range, has a relatively good application prospect and is expected to be widely applied to organic synthesis, fine chemical engineering and pharmaceutical industry.
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Paragraph 0033-0035
(2021/06/26)
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- Synthesis of Oxindole Derivatives via Intramolecular C–H Insertion of Diazoamides Using Ru(II)-Pheox Catalyst
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This work presented the efficient intramolecular aromatic C–H insertion of diazoacetamide. The 1a–1o diazo compounds (except for 1k) were converted into their corresponding oxindoles via an intramolecular C–H insertion reaction in the presence of a Ru catalyst. The Ru-Pheox catalyst was shown to be highly efficient in this transformation in terms of the regioselectivity, producing the desired products in excellent yield (99%). The efficiency of the Ru catalyst reached 580 (TON) and 156 min?1 (TOF).
- Phan Thi Thanh, Nga,Dang Thi Thu, Huong,Tone, Masaya,Inoue, Hayato,Iwasa, Seiji
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- Candida antarctica lipase-B-catalyzed kinetic resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles
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Candida antarctica (CAL-B) lipase-catalyzed resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles has been performed to obtain (R)-1,3-dialkyl-3-acetoxymethyl oxindoles with up to 99% ee and (S)-1,3-dialkyl-3-hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)-3-allyl-3-hydroxymethyl oxindole to (3S)-1′-benzyl-5-(iodomethyl)-4,5-dihydro-2H-spiro[furan-3,3′-indolin]-2′-one. The optically active 3-substituted-3-hydroxymethyl oxindoles and spiro-oxindoles are among the key synthons in the synthesis of potentially biologically active molecules.
- Kumar, Naveen,Kumar, Akshay,Sahoo, Subash Chandra,Chimni, Swapandeep Singh
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p. 1377 - 1394
(2020/11/23)
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- Acylation of oxindoles using methyl/phenyl estersviathe mixed Claisen condensation - an access to 3-alkylideneoxindoles
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Predominantly, aggressive acid chlorides and stoichiometric coupling reagents are employed in the acylating process for synthesizing carbonyl tethered heterocycles. Herein, we report simple acyl sources,viz. methyl and phenyl esters, which acylate oxindolesviathe mixed Claisen condensation. This straightforward protocol is mediated by LiHMDS and KOtBu and successfully applied to a wide range of substrates. It is a noteworthy transformation that skips the stepwise generation of enolates and acylation, and the reaction is performed at a moderate temperature with no side reactions. This protocol produces the first examples ofortho-substituents in an aryl ring flanked with electron-donating and electron-withdrawing substrates. Interestingly, robust organometallic ferrocenyl methyl ester cleaved under these conditions with ease. Furthermore, biologically important Tenidap's analog was synthesized by this protocol.
- Gandhi, Thirumanavelan,Nagaraja, C. M.,Panyam, Pradeep Kumar Reddy,Rajeshwaran, Purushothaman,Sreedharan, Ramdas,Yadav, Saurabh
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p. 3843 - 3847
(2020/06/03)
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- Preparation method of optically active 2-aryl spiro [cyclopentane-1, 3'-indole]-3-formaldehyde
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The invention discloses a preparation method of optically active 2-aryl spiro [cyclopentane-1, 3'-indole]-3-formaldehyde. The preparation method comprises the following steps: adding vinyl oxoindole spiro-cyclopropane and olefine aldehyde as raw materials into a solvent, respectively adding secondary amine, palladium salt, a ligand and an additive, stirring the mixture at room temperature, then removing the solvent, and purifying by virtue of a rapid column chromatography, so as to obtain the optically active 2-aryl spiro [cyclopentane-1, 3'-indole]-3-formaldehyde. The 2-aryl spiro [cyclopentane-1, 3'-indole]-3-formaldehyde prepared by the method has the characteristics of mild reaction conditions, simple process, controllable optical activity, high yield and the like.
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Paragraph 0138-0140; 0142-0143
(2020/10/05)
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- Enantioselective Synthesis of Multisubstituted Spirocyclopentane Oxindoles Enabled by Pd/Chiral Rh(III) Complex Synergistic Catalysis
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An asymmetric [3 + 2]-cycloaddition reaction of α,β-unsaturated 2-acyl imidazoles with spirovinylcyclopropanyl-2-oxindoles catalyzed synergistically by an achiral palladium(0) catalyst and a chiral-at-metal rhodium(III) complex has been developed. A series of biologically important 3-spirocyclopentane-2-oxindoles with four contiguous stereocenters were synthesized in high yields (up to 99%) with excellent stereoselectivities (up to 99% ee, 20:1 dr).
- Wan, Qian,Chen, Liang,Li, Shiwu,Kang, Qiang,Yuan, Yaofeng,Du, Yu
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supporting information
p. 9539 - 9544
(2020/12/21)
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- Palladium-catalysed ring-opening [3 + 2]-annulation of spirovinylcyclopropyl oxindole to diastereoselectively access spirooxindoles
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A novel palladium-catalysed ring-opening [3 + 2]-annulation of spirovinylcyclopropyl oxindole with α,β-unsaturated nitroalkenes is reported. A series of spirooxindole derivatives were synthesized in high yields and good to excellent diastereoselectivities. This developed protocol offers a new and efficient pathway for the assembly of spirooxindoles.
- Xiao, Jun-An,Cheng, Xiu-Liang,Li, Yu-Chun,He, Yi-Miao,Li, Jin-Lian,Liu, Zhi-Ping,Su, Wei,Xia, Peng-Ju,Yang, Hua
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supporting information
p. 103 - 107
(2019/01/22)
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- Construction of Bispirooxindole Heterocycles via Palladium-Catalyzed Ring-Opening Formal [3 + 2]-Cycloaddition of Spirovinylcyclopropyl Oxindole and 3-Oxindole Derivatives
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A palladium-catalyzed ring-opening oxo-formal [3 + 2]-cycloaddition reaction of novel donor-acceptor spirovinylcyclopropyl oxindole with 3-oxindole is described. The developed protocol provides facile access to oxo-bispirooxindole derivatives in good yields (up to 82% yield) with excellent diastereoselectivities (up to 20:1 dr).
- Xiao, Jun-An,Li, Yu-Chun,Luo, Zhi-Jin,Cheng, Xiu-Liang,Deng, Zhi-Xiong,Chen, Wen-Qiang,Su, Wei,Yang, Hua
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- Schmidt Reaction of ω-Azido Valeryl Chlorides Followed by Intermolecular Trapping of the Rearrangement Ions: Synthesis of Assoanine and Related Pyrrolophenanthridine Alkaloids
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The Schmidt reaction of ω-azido valeryl chlorides in the presence of an additional nucleophile was explored. The arenes, alcohols, and amines were demonstrated as the intermolecular trapping reagents for isocyanate ion and N-acyliminium ion from the Schmidt rearrangement, affording the corresponding products with moderate to excellent yields. Two 2-oxoindoles from the reaction were successfully converted into four natural alkaloids, namely, assoanine, anhydrolycorine, oxoassoanine, and anhydrolycorinone.
- DIng, Shao-Lei,Ji, Yang,Su, Yan,Li, Rui,Gu, Peiming
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p. 2012 - 2021
(2019/02/14)
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- Cyclization and oxidation of o-bromophenylacetamides for the synthesis of oxindoles and isoindigoes
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N-substituted oxindoles were obtained through a facile KOH/DMSO promoted intramolecular cyclization of o-bromophenylacetamides in good yields. Furthermore, isoindigo derivatives were readily synthesized through sequential intramolecular cyclization, oxida
- Liu, Liang,Song, Lei,Guo, Yujun,Min, Dewen,Shi, Tianchao,Zhang, Wu
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supporting information
p. 354 - 359
(2017/12/26)
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- The Power of Triplet and Singlet Oxygen in Synthesis: 2-Oxindoles, 3-Hydroxy-2-oxindoles, and Isatins from Furans
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A straightforward synthesis of substituted 2-oxindoles, 3-hydroxy-2-oxindoles, and isatins has been developed. Easily accessible furans were transformed into tetrahydropyranopyrrolones by a singlet oxygen initiated cascade reaction sequence. An acid-catal
- Triantafyllakis, Myron,Sfakianaki, Kalliopi,Kalaitzakis, Dimitris,Vassilikogiannakis, Georgios
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p. 3631 - 3634
(2018/06/26)
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- Palladium-catalyzed silaborative carbocyclizations of 1,6-diynes
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An addition/cyclization reaction of 1,6-diynes was developed for the synthesis of highly substituted 1,2-dialkylidenecycloalkanes. In this work, 1,6-diynes reacted with (dimethylphenylsilyl)pinacol-borane in the presence of a palladium catalyst to afford 1,2-dialkylidenecycloalkanes bearing silyl and boryl groups with a (Z,Z)-configuration in good to excellent yields. Moreover, the corresponding products could be easily converted into other synthetically useful compounds. This protocol provides an efficient and practical method of heteroelement-element linkage addition to the unsaturated 1,6-diynes.
- Zhang, Qian,Liang, Qiu-Ju,Xu, Jian-Lin,Xu, Yun-He,Loh, Teck-Peng
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p. 2357 - 2360
(2018/03/13)
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- Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles
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Rationally designed fluorene-based mono- and bimetallic Pd-PEPPSI complexes were synthesized and demonstrated to be effective for the one-pot sequential α-arylation/alkylation of oxindoles. This streamlined approach offers efficient access to functionalized 3,3-disubstituted oxindoles in excellent yields (up to 89%) under mild reaction conditions.
- Reddy Panyam, Pradeep Kumar,Ugale, Bharat,Gandhi, Thirumanavelan
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p. 7622 - 7632
(2018/06/22)
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- Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates
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The previously unexplored Grignard addition to oxindoles provides a regiospecific approach to 2- and 2,3-disubstituted indole derivatives in high yields via a one-pot aromatization driven dehydration pathway. This method allows a convenient preparation of diallyl indoles that are used as ring-closing metathesis (RCM) precursors for the orthogonal synthesis of pyrido[1,2-a]indoles and carbazoles. The synthetic utility of this method is illustrated by the synthesis of a microtubulin inhibitor and naturally occurring carbazole alkaloids.
- Mandal, Tirtha,Chakraborti, Gargi,Karmakar, Shilpi,Dash, Jyotirmayee
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p. 4759 - 4763
(2018/08/24)
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- Reactivity of spiroanthraceneoxazolidines with cyclopropanes: An approach to the oxindole alkaloid scaffold
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The reaction of N-methylspiro[anthracene-oxazolidine] with spiro[cyclopropane-3,3′-indolin]-2-ones in the presence of MgI2 formed the corresponding spiro[pyrrolidine-3,3′-indolin]-2-ones in 42–65% yields. The use of N-benzylspiro[anthracene-oxazolidine] in this reaction led to the formation of a mixture of the corresponding N-methyl- and N-benzylpyrrolidines.
- Buev, Evgeny M.,Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Y.
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p. 3409 - 3412
(2018/08/20)
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- Cinchona-alkaloid-catalyzed enantioselective hydroxymethylation of 3-fluorooxindoles with paraformaldehyde
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Cinchona-alkaloid-catalyzed hydroxymethylation of 3-fluorooxindoles using paraformaldehyde as the C1 unit was achieved. A wide range of 3-fluorooxindoles was successfully reacted to give the corresponding 3-fluoro-3-hydroxymethyloxindoles with high efficiency and moderate to good enantioselectivity.
- Zhao, Jian-bo,Ren, Xinfeng,Zheng, Bu-quan,Ji, Jian,Qiu, Zi-bin,Li, Ya
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- Method for synthesizing indole-2-ketone compound
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The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a method for synthesizing an indole-2-ketone compound. Indole-2-ketone compound synthesis is difficultly industrialized due to the problems of poor yield, cost and environmental protection in the prior art, the method includes the steps: taking a compound X as a catalyst in a hydrous organic solvent; performing reaction on indole and water under the condition of oxidizing agents to obtain the indole-2-ketone compound. The compound X is preferably iodine, and the indole-2-ketone compound is applicable to the field of organic synthesis and medicine.
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Paragraph 0065; 0067
(2018/11/03)
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- Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation
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A practical conversion of indoles into the corresponding 2-oxindoles is achieved efficiently using a hypervalent iodine reagent. This oxidation is amenable to different substituted indoles, and allows the synthesis of a wide range of synthetically valuable substituted 2-oxindoles in up to 90 % yield. Furthermore, Ropinirole, a drug used to alleviate the symptoms of Parkinson's disease, was synthesized in three steps in an overall yield of 44 % using this method.
- Jiang, Xinpeng,Zheng, Cong,Lei, Lijun,Lin, Kai,Yu, Chuanming
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p. 1437 - 1442
(2018/04/06)
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- Method for directly synthesizing substituted 2-indolone by substituted indole under neutral condition
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The invention relates to a method for directly synthesizing substituted 2-indolone by substituted indole under the neutral condition. The method comprises the following steps of sequentially adding organic solvents and water according to the proportion of 1:1-1:20 at the room temperature; then, adding high-iodine reagents; raising the temperature to 40 to 160 DEG C; then, adding indole; performingreaction for 1 to 8 hours to obtain the substituted 2-indolone compounds. The method has the main innovation point that under the neutral condition, substituted 2-indolone is directly synthesized through indole oxidization; the use of strong acid reagents is avoided. The method has the advantages that the raw materials are cheap and can be easily obtained; the operation is simple and convenient;the substrate universality is high; the reaction yield is high, and the like.
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Paragraph 0036-0037
(2018/07/06)
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- Copper powder-catalyzed chelation-assisted cascade reaction of: O -chloroarylacetic acids with amines under solvent- and ligand-free conditions: Synthesis of oxindoles
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An efficient method to construct oxindole scaffolds from o-chloroarylacetic acids/esters with amines has been explored. This cascade protocol involves the in situ generation of o-aminoarylacetic acid derivatives by the copper powder catalyzed and weak O-chelation assisted Ullmann amination of unactivated C-Cl bonds under air, and solvent-/ligand-free conditions followed by annulative N-acylation.
- Li, Jiang-Sheng,Chen, Guo-Qin,Yang, Qian,Li, Zhi-Wei,Liu, Ci-Zhi,Huang, Peng-Mian
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p. 45227 - 45231
(2017/10/13)
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- A 2 - indolone derivatives and its preparation method
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The invention relates to 2-indolone derivatives and a preparation method thereof. The structural formula is disclosed in the specification, wherein R1 is H, 4-Cl or 5-OCH3; and R2 is n-Bu, Cy, Bn, (4-OCH3)-Bn, i-Pr, n-C12H25, (4-Cl)-Bu, (4-Cl)-Bn or (4-OC
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Paragraph 0042; 0043; 0044; 0045; 0046
(2017/08/25)
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- Palladium-catalysed intramolecular carbenoid insertion of α-diazo-α-(methoxycarbonyl)acetanilides for oxindole synthesis
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A novel, selective palladium-catalysed carbenoid C(aryl)-H insertion of α-diazo-α-(methoxycarbonyl)acetanilides leading to oxindoles is described.
- Solé, Daniel,Pérez-Janer, Ferran,Fernández, Israel
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p. 3110 - 3113
(2017/03/17)
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- Autoxidation/Aldol Tandem Reaction of 2-Oxindoles with Ketones: A Green Approach for the Synthesis of 3-Hydroxy-2-Oxindoles
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In the presence of tetrabutylammonium fluoride and molecular sieves (MS) 4 ? in DMF, an efficient autoxidation reaction of 2-oxindoles with ketones under air at room temperature has been developed. This approach may provide a green, practical, and metal-free protocol for a wide range of biologically important 3-hydroxy-3-(2-oxo-alkyl)-2-oxindoles.
- Zhang, Qing-Bao,Jia, Wen-Liang,Ban, Yong-Liang,Zheng, Yong,Liu, Qiang,Wu, Li-Zhu
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p. 2595 - 2598
(2016/02/27)
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- Novel Methodology for the Efficient Synthesis of 3-Aryloxindoles: [1,2]-Phospha-Brook Rearrangement-Palladium-Catalyzed Cross-Coupling Sequence
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A novel methodology for the efficient synthesis of 3-aryloxindoles from isatin derivatives was developed. The methodology involves the formation of an oxindole having a phosphate moiety at the C-3 position via the [1,2]-phospha-Brook rearrangement under Bronsted base catalysis followed by palladium-catalyzed cross-coupling with aryl boron reagents. The one-pot synthesis of 3-aryloxindoles from isatin derivatives is also described.
- Kondoh, Azusa,Takei, Akira,Terada, Masahiro
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p. 1848 - 1853
(2016/07/16)
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- Pushing the boundaries of vinylogous reactivity: Catalytic enantioselective Mukaiyama aldol reactions of highly unsaturated 2-silyloxyindoles
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The first example of catalytic, enantioselective hypervinylogous Mukaiyama aldol reaction (HVMAR) involving multiply unsaturated 2-silyloxyindoles is reported. The reaction utilizes a chiral Lewis base-catalyzed Lewis acid-mediated technology to deliver homoallylic 3-polyenylidene 2-oxindoles with extraordinary levels of regio-, enantio-, and geometrical selectivity. This work highlights a subtle yet decisive influence of the indole N-substituents on the propagation of the vinylogous reactivity space of the donor substrates up to ten bonds away from the origin of the vinylogy effect. Analysis of the 13C NMR chemical shifts of the C-ω remote site within homologous silyloxyindole donors enabled rationalization of the results and easy qualitative prediction of the HVMAR reactivity/inertia toward a given aldehyde acceptor.
- Curti, Claudio,Sartori, Andrea,Battistini, Lucia,Brindani, Nicoletta,Rassu, Gloria,Pelosi, Giorgio,Lodola, Alessio,Mor, Marco,Casiraghi, Giovanni,Zanardi, Franca
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p. 6433 - 6442
(2015/04/22)
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- Oxidative dimerization of 2-oxindoles promoted by KOtBu-I2: Total synthesis of (±)-folicanthine
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A transition-metal-free oxidative coupling of 2-oxindoles has been demonstrated in the presence of 1.2 equiv each of potassium tert-butoxide and iodine. The method yields a diverse range of structurally different homo- and heterodimerized 2-oxindoles bearing vicinal all-carbon quaternary centers of great synthetic importance. A radical-driven pathway has been tentatively proposed.
- Ghosh, Santanu,Chaudhuri, Saikat,Bisai, Alakesh
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p. 1373 - 1376
(2015/03/30)
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- An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)-H oxidation and intramolecular C-N bond formation of 2′-aminoacetophenones
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A novel molecular I2-catalyzed synthesis of isatins through C(sp3)-H oxidation and intramolecular C-N bond formation of 2′-aminoacetophenones with excellent yields up to 97% under transition metal, base, additive, peroxide and ligand free conditions is described. The present protocol is suitable for gram scale synthesis of isatins and retained its high yield. Further, the synthetic utility of this present reaction towards synthesis of bioactive 3-hydroxy-2-oxindoles and oxindoles is demonstrated. This journal is
- Rajeshkumar, Venkatachalam,Chandrasekar, Selvaraj,Sekar, Govindasamy
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p. 8512 - 8518
(2014/12/10)
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- Palladium-catalyzed carbonylative α-arylation of 2-oxindoles with (Hetero)aryl bromides: Efficient and complementary approach to 3-acyl-2-oxindoles
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An efficient Pd-catalyzed carbonylative α-arylation of 2-oxindoles with aryl and heteroaryl bromides for the one-step synthesis of 3-acyl-2-oxindoles has been developed. This reaction proceeds efficiently under mild conditions and is complementary to the
- Lian, Zhong,Friis, Stig D.,Skrydstrup, Troels
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supporting information
p. 9582 - 9586
(2014/11/08)
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- ISATIN DERIVATIVES, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USE THEREOF
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One aspect of the invention relates to novel isatin derivative compounds and the pharmaceutical composition thereof. Another aspect of the invention relates to methods of using the isatin derivative compounds disclosed herein and the pharmaceutical compos
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Paragraph 0138-0139
(2013/09/12)
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- Phosphane-free Pd0-catalyzed cycloamination and carbonylation with Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3: Preparation of benzocyclic amines and benzolactams
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Phosphane-free Pd0-catalyzed intramolecular aromatic amination was studied. o-Halophenethylamines and 3-(o-halophenyl)propylamines were found to be transformed into indolines and quinolines in a catalytic system based on Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3. Application of the method to substrates containing isoquinoline rings- the 1-(o-bromobenzyl)-3,4-dihydroisoquinolines 6, the 1-(o-bromobenzyl)-1,2,3,4-tetrahydroisoquinolines 7, and the 1-(o-bromophenethyl)isoquinolines 9- provided the indolo[2,1-a]isoquinoline and dibenzo[a,f]quinolizine ring systems 8 and 10. Extension of the method to β-carbolines (compounds 11, 12, and 17) produced the benz[f]indolo[2,3-a] indolizine-13-ones 15 and the benz[f]indolo[2,3-a]quinolizine 18. The benzo[f]pyrido[3,4-a]indolizine and indolo[f]pyrido[3,4-a]indolizin-12-one ring systems 27 and 31 were built in a similar manner. It was also found that under an atmosphere of CO the same catalytic system produced the corresponding benzolactams, the isoquino[2,1-a][2,7]naphthyridine 34 and the indolo[2,3-a]pyrido[g]quinolizin-8-one 36 [(±)-dihydronauclefine] in good yields. Copyright
- Harada, Rika,Nishida, Naoto,Uchiito, Shiho,Onozaki, Yu,Kurono, Nobuhito,Senboku, Hisanori,Masao, Tokuda,Ohkuma, Takeshi,Orito, Kazuhiko
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p. 366 - 379
(2012/02/04)
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- Catalytic enantioselective desymmetrisation as a tool for the synthesis of hodgkinsine and hodgkinsine B
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Two palladium-catalysed amination protocols are deployed in the desymmetrisation of the complex dimeric alkaloid meso-chimonanthine. The power of these transformations is showcased in an efficient formal and total synthesis of the natural products hodgkinsine and hodgkinsine B, respectively. Two palladium-catalysed amination protocols are deployed in the desymmetrisation of the complex dimeric alkaloid meso-chimonanthine. The power of these transformations is showcased in efficient formal and total synthesis of the natural products hodgkinsine and hodgkinsine B (see figure), respectively. Copyright
- Snell, Robert H.,Durbin, Matthew J.,Woodward, Robert L.,Willis, Michael C.
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supporting information
p. 16754 - 16764
(2013/03/28)
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- Platinum-catalyzed oxoarylations of ynamides with nitrones
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A new platinum-catalyzed oxoarylation of ynamides with nitrones is reported. Cascade sequences for the synthesis of indolin-2-ones via NaBH 3CN reduction in situ of the initially formed oxoarylation products are also developed.
- Bhunia, Sabyasachi,Chang, Chin-Jung,Liu, Rai-Shung
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supporting information
p. 5522 - 5525,4
(2020/10/15)
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- Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: Reaction development and applications
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We report a full account of our work towards the development of Mo-catalyzed asymmetric allylic alkylation reactions with 3-alkyloxindoles as nucleophiles. The reaction is complementary to the Pd-catalyzed reaction with regard to the scope of oxindole nucleophiles. A number of 3-alkyloxindoles were alkylated successfully under mild conditions to give products with excellent yields and good-to-excellent enantioselectivities. Applications of this method to the preparation of indoline alkaloids such as (-)-physostigmine, ent-(-)-debromoflustramine B, and the indolinoquinoline rings of communesin B are reported.
- Trost, Barry M.,Zhang, Yong
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p. 2916 - 2922
(2011/05/02)
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- KINASE INHIBITORS AND METHOD OF TREATING CANCER WITH SAME
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The invention is directed to a compound represented by the following structural formula pharmaceutically acceptable salts thereof: (I). Compounds represented by this structural formula are kinase inhibitors and are therefore disclosed herein for the treatment of cancer. Definitions for the variables in the structural formula are provided herein.
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- Ultrasound promoted clay catalyzed efficient and one pot synthesis of substituted oxindoles
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A simple facile, one-pot synthesis of oxindoles in reasonable purity is reported via intramolecular Friedal-Craft cyclization. Clay KSF is an inexpensive, efficient and mild catalyst for the synthesis of substituted oxindoles by the reaction of chloroacetyl chloride and various anilines under the influence of ultrasonic irradiation under solvent-free conditions. The remarkable advantages of this method are the simple experimental procedures, short reaction times, high yields of products, suitability for a wide variety of substituents, and the green aspects through the avoidance of toxic catalyst and solvents.
- Dandia,Bhati,Jain,Sharma
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experimental part
p. 1143 - 1147
(2012/03/10)
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- Ruthenium-catalyzed alkylation of oxindole with alcohols
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(Chemical Equation Presented) An atom-economical and solvent-free catalytic procedure for the mono-3-alkylation of oxindole with alcohols is described. The reaction is mediated by the in situ generated catalyst from RuCl 3·xH2O and P
- Jensen, Thomas,Madsen, Robert
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supporting information; experimental part
p. 3990 - 3992
(2009/12/25)
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- A versatile synthesis of unsymmetrical 3,3′-bioxindoles: Stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins
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(Chemical Equation Presented) A new synthesis of 3,3′-bioxindoles is reported that is well suited for the preparation of unsymmetrical structures. In the key step, 3-hydroxy-3,3′-bioxindoles are constructed by Mukaiyama aldol reaction of 2-siloxyindoles w
- Ellis, J. Michael,Overman, Larry E.,Tanner, Huw R.,Wang, Jocelyn
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supporting information; experimental part
p. 9151 - 9154
(2009/04/04)
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- Palladium-catalyzed α-arylation of oxindoles
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(Chemical Equation Presented) A catalyst generated from Pd(dba)2 and the bulky electron-rich phosphine ligand 2-(dicyclohexylphosphino)- 2′,4′, 6′-tri- i-propyl-1-1′-biphenyl is effective for the α-arylation of oxindoles. Generation of the pota
- Durbin, Matthew J.,Willis, Michael C.
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supporting information; experimental part
p. 1413 - 1415
(2009/04/12)
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- Synthesis of 1-substituted 3-pyridinylmethylidenylindolin-2-ones and 1-substituted 3-quinolinylmethylidenylindolin-2-ones as the enhancers of ATRA-induced differentiation in HL-60 cells
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As part of our continuing search for potential differentiation agents, 1-benzyl-3-(4-pyridinylmethylidenyl)indolin-2-one (14) was selected as lead compound, and its new pyridinyl and quinolinyl analogs were synthesized and evaluated for differentiation-in
- Hung, Chi-Ying,Hsu, Mei-Hua,Huang, Li-Jiau,Hwang, Chrong-Shiong,Lee, On,Wu, Chen-Yi,Chen, Chih-Hung,Kuo, Sheng-Chu
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p. 4222 - 4232
(2008/12/20)
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- Synthesis of the dibenzopyrrocoline alkaloid skeleton: indolo[2,1-a]isoquinolines and related analogues
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The indolo[2,1-a]isoquinoline and pyrrolo[2,1-a]isoquinoline nuclei have been synthesized from N-benzylindole or ethyl 1H-indol-1-ylacetate and N-benzylpyrrole precursors, respectively. Firstly, at C-2 of either the indole or pyrrole nucleus, aromatic rin
- L?tter, Angelique N.C.,Pathak, Rakhi,Sello, Thato S.,Fernandes, Manuel A.,van?Otterlo, Willem A.L.,de Koning, Charles B.
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p. 2263 - 2274
(2007/10/03)
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- Synthesis of novel phenylnaphthyl phosphines and their applications to Pd-catalyzed intramolecular amidation
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Novel phenylnaphthyl phosphines were prepared and applied to the Pd-catalyzed intramolecular amidation. Both ligands gave good to excellent yields in the synthesis of five-, six-, and seven-membered rings from halo-amides and carbamates. Georg Thieme Verl
- Kitamura, Yuki,Hashimoto, Ayano,Yoshikawa, Seiji,Odaira, Jun-Ichi,Furuta, Takumi,Kan, Toshiyuki,Tanaka, Kiyoshi
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p. 115 - 117
(2007/10/03)
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- Total synthesis of (-)-spirotryprostatin B: Synthesis and related studies
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The total synthesis of spirotryprostatin B, a cytostatic spiro[pyrrolidine-3,3′-oxindole] alkaloid, is described. The key step of the synthetic approach consists of the application of the Mgl 2-mediated ring-expansion reaction of a spiro[cyclopropane-1, 3′-oxindole] with an aldimine, leading to rapid assembly of the spirotryprostatin core. The route documents the installation of the prenyl side chain by Julia-Kocienski olefination of a key aldehyde precursor, a transformation that ultimately allows for facile synthesis of analogues and facilitates structure-activity relationships studies.
- Marti, Christiane,Carreira, Erick M.
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p. 11505 - 11515
(2007/10/03)
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- Microwave-assisted sequential amide bond formation and intramolecular amidation: A rapid entry to functionalized oxindoles
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(Chemical Equation Presented) A general method has been developed for the synthesis of N-substituted oxindoles. The two-step process involves initial microwave-assisted amide bond formation between 2-halo-arylacetic acids and various alkylamines and anilines, followed by a palladium-catalyzed intramolecular amidation under aqueous conditions. In the case of alkylamines, the procedure can be carried out as a one-pot process without isolation of the intermediate amide.
- Poondra, Rajamohan R.,Turner, Nicholas J.
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p. 863 - 866
(2007/10/03)
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- Synthesis of substituted oxindoles from α-chloroacetanilides via palladium-catalyzed C - H functionalization
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A novel method for the synthesis of oxindoles is described. In the presence of catalytic palladium acetate and 2-(di-tert-butylphosphino)biphenyl, α-chloroacetanilides are converted to oxindoles in good to excellent yields with high functional group compatibility using triethylamine as a stoichiometric base. The cyclization is highly regioselective, obviating the need for prefunctionalized arenes. Plausible mechanistic pathways for the reaction are discussed. Copyright
- Hennessy, Edward J.,Buchwald, Stephen L.
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p. 12084 - 12085
(2007/10/03)
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- A short and efficient synthesis of N-substituted indol-2-ones (oxindoles)
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A short and high yielding process has been developed for the synthesis of N-(4-piperidinyl)-indol-2-ones. This strategy also constitutes a general route to N-substituted indol-2-ones.
- Forbes, Ian T
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p. 6943 - 6945
(2007/10/03)
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