- Supramolecular synthesis of 3-indolyl-3-hydroxy oxindoles under neutral conditions in water
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(Chemical Equation Presented) Various 3-indolyl-3-hydroxy oxindoles were prepared for the first time by supramolecular catalysis involving the reaction of β-CD:isatin complexes with indoles under neutral conditions in water. β-Cyclodextrin can be recovered and reused a number of times without loss of activity.
- Kumar, V. Pavan,Reddy, V. Prakash,Sridhar,Srinivas,Narender,Rao, K. Rama
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- Application of cellulose/chitosan grafted nano-magnetites as efficient and recyclable catalysts for selective synthesis of 3-indolylindolin-2-ones
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Cellulose grafted to nano-magnetites was found to be an efficient biopolymer composite for catalysis of Friedel-Crafts reaction between isatins and indoles, leading to selective synthesis of 3-hydroxy-3-indolylindolin-2- ones. The catalysis process is likely effected by a mass of hydroxyl groups arranged along the backbone of cellulose fibers coated on surface of the nano-sized magnetite support, where they get exposed to the adsorbed substrates. Synergistic push-pull effects, reminiscent of the soft catalysis of metal-less enzymes, via proton donating-accepting functions of the hydroxyl groups anchored on surface of the cellulose shell were invoked to explain the clean and selective bioorganocatalysis of 3-indolylindolin-2-one formation. In addition, more improvement in this selective catalytic performance was realized by employing the magnetite nano-particles coated with chitosan shell.
- Rad-Moghadam, Kurosh,Dehghan, Negin
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- Electro-organic synthesis of nanosized particles of 3-hydroxy-3-(1H-indol- 3-yl)indolin-2-one derivatives
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This article describes an electrochemical method for preparation of nanosized particles of 3-hy-droxyoxindoles. The method is based on the reaction of isatins with indoles in propanol employing an undivided cell in the presence of NaBr as an electrolyte. The product was characterized after purification using infrared (IR), 1H nuclear magnetic resonance (NMR), 13C NMR, mass spectrometry (MS), and scanning electron microscopy (SEM).
- Makarem,Fakhari,Mohammadi
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- Cu(I)-catalyzed one-pot reactions of isatins, indoles, and amines toward unsymmetrically substituted 2-carbonylarylureas
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A series of unsymmetrical arylureas was obtained by the one-pot method for reacting isatins with indoles incorporating primary amino moieties, a significant heterocyclic skeleton for diverse pharmaceutically active structures. The reaction proceeds through Cu(I)-catalyzed C2–C3 bond of the ring-opening isatins and then expands the substrates in the optimum conditions. Furthermore, selected compounds 4b and 4k exhibit moderate to good anti-schistosomicidal activities.
- Peng, Xiangjun,Xu, Xianyun,Chen, Shuangyang,Tian, Zeng,Liu, Liangxian,Liu, Qian
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- Triton b-assisted, efficient, and convenient synthesis of 3-indolyl-3-hydroxy oxindoles in aqueous medium
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An efficient and convenient synthesis of 3-indolyl-3-hydroxy oxindole is described by the reaction of isatin with indole in the presence of Triton B in an aqueous medium.
- Meshram,Kumar, D. Aravind,Goud, P. Ramesh,Reddy, B. Chennakesava
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- Preparation, characterization, and catalysis application of nano-rods zinc oxide in the synthesis of 3-indolyl-3-hydroxy oxindoles in water
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ZnO nano-rods is synthesized successfully by a new method employing Zn(OAc)2·2H2O, NH3 and polyethylene glycol (PEG, Mw = 2000). X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and BET surface area measurement were used to characterize the structure and morphology of the catalyst. Nano-rods ZnO has been found highly effective and recyclable catalyst for synthesis of 3-indolyl-3-hydroxy oxindole derivatives by Friedel-Crafts reaction of indole with isatins in excellent yields, in water.
- Hosseini-Sarvari, Mona,Tavakolian, Mina
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- Organocatalytic Asymmetric Synthesis of Spiro-Bridged and Spiro-Fused Heterocyclic Compounds Containing Chromane, Indole, and Oxindole Moieties
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Following the reactivity inversion strategy, two different two-step sequences were designed and successfully applied to the asymmetric synthesis of spiro-bridged and spiro-fused heterocyclic compounds, which combined chromane, indole, and oxindole, three
- You, Zhi-Hao,Chen, Ying-Han,Tang, Yu,Liu, Yan-Kai
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- An efficient Friedel-Crafts alkylation for the synthesis of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-diaryl oxindoles catalyzed by Dabco-based ionic liquids in water
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A convenient and rapid method for the syntheses of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-diaryl oxindoles has been developed by using Dabco-based ionic liquid catalysts. The two ionic liquid catalysts, [Dabco-H][BF4] and [Dabco-H][HSO4] were found to be highly efficient catalysts for controlled 3-indolylation of isatins in water. When [Dabco-H][BF4] was employed as the catalyst in water at 55 °C, the reaction between isatins and indoles stops at the step of addition of the two components and afforded 3-indolyl-3-hydroxy oxindoles. While increasing the reaction temperature to 90 °C, the catalyst [Dabco-H][HSO4] could drive the reaction further and afford symmetrical 3,3-diindolyl oxindoles. By using the two kinds of ionic liquids, a two-step protocol for the efficient synthesis of unsymmetrical 3,3-diaryl oxindoles has also been developed. The use of water as the reaction medium makes the process environmentally benign. The catalysts can be recycled five times without activity loss.
- Tong, Jun,Huang, Lu-Shan,Xu, Da-Zhen
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- An efficient synthesis of 3-indolyl-3-hydroxy oxindoles and 3,3-di(indolyl)indolin-2-ones catalyzed by sulfonated β-CD as a supramolecular catalyst in water
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Sulfonated-β-cyclodextrin (β-CD-SO3H) promoted efficient and fast electrophilic substitution reaction of indoles with various isatins reflux in water is reported affording various 3-indolyl-3-hydroxy oxindoles and 3,3-di(indolyl)indolin-2-ones in good to excellent yields in short reaction time.
- Tayade, Yogesh A.,Patil, Dipak R.,Wagh, Yogesh B.,Jangle, Asha D.,Dalal, Dipak S.
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- Lambert Salt-Initiated Development of Friedel–Crafts Reaction on Isatin to Access Distinct Derivatives of Oxindoles
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Herein, a mild metal-free and efficacious route for the synthesis of biologically important 3-aryl oxindole derivatives is described. Using Lambert salt-initiated hydroarylation of isatin, a diverse array of monoarylated products, symmetrical/unsymmetrical double-arylated products, and deoxygenated hydroarylated products could be synthesized from the single starting substrate in good to excellent yields. A preliminary mechanistic study revealed that the reaction proceeds via a monoarylated product followed by a nucleophilic attack by another electron-rich arene nucleophile under mild conditions. The potential of newly synthesized symmetric/unsymmetric 3,3-disubstituted oxindole, 3-substituted 3-hydroxy oxindoles, 3,3-di(indolyl)indolin-2-ones, and α-aryl oxindoles as valuable building blocks is further illustrated.
- Khan, Jabir,Tyagi, Aparna,Yadav, Naveen,Mahato, Rina,Hazra, Chinmoy K.
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p. 17833 - 17847
(2021/12/17)
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- Oxidative cyanation of 2-oxindoles: formal total synthesis of (±)-gliocladin C
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Efficient oxidative direct cyanations of 3-alkyl/aryl 2-oxindoles using Cyano-1,2-BenziodoXol-3(1H)-one (CBX) (2a) have been reported under 'transition metal-free' conditions to synthesize a wide variety of 3-cyano 3-alkyl/aryl 2-oxindoles sharing an all-carbon quaternary center under additive-free conditions. The application of this process is shown by the formal total synthesis of (±)-gliocladin C (11c) in a few steps.
- Bisai, Alakesh,Das, Mrinal Kanti,De, Subhadip,Maity, Arindam,Naskar, Malay,Roy, Avishek
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supporting information
p. 1679 - 1684
(2020/03/05)
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- 3-Hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one as a versatile intermediate for retro-Henry and Friedel-Crafts alkylation reactions in aqueous medium
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The first example of a retro-Henry type reaction is reported using 3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-ones which are prepared via catalyst-free Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin. These compounds were used
- Nagaraju, Sakkani,Sathish, Kota,Paplal, Banoth,Satyanarayana, Neeli,Kashinath, Dhurke
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supporting information
p. 14045 - 14050
(2019/09/18)
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- 2D-2D Nanocomposite of MoS2-Graphitic Carbon Nitride as Multifunctional Catalyst for Sustainable Synthesis of C3-Functionalized Indoles
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A nanocomposite of two-dimensional MoS2 supported on graphitic C3N4 nanosheets has been prepared by a facile ultrasonication method followed by demonstrating its ability to catalyze the synthesis of several indole derivatives. The as-prepared nanocomposite catalyst was characterized in detail by using different microscopic and spectroscopic techniques to understand its structure and physicochemical properties. Subsequently, this nanocomposite catalyst was used as a heterogeneous multifunctional catalyst to synthesize several C3-functionalized indoles in the aqueous medium. The employed strategy also provided very good catalyst recyclability and versatility for the synthesis of various precursors of medicinally significant indoles, such as serotonin, melatonin, and various β-carboline alkaloids. In addition, a natural product derivate has been prepared on the gram-scale by using this methodology. Furthermore, high atom economy (100 %) and lower E-factor (0.042) makes this strategy a sustainable approach for the synthesis of C3-functionalized indoles.
- Bahuguna, Ashish,Kumar, Ashwani,Kumar, Suneel,Chhabra, Tripti,Krishnan, Venkata
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p. 3121 - 3132
(2018/07/29)
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- Thiourea-Catalyzed Enantioselective Malonate Addition onto 3-Sulfonyl-3′-indolyl-2-oxindoles: Formal Total Syntheses of (-)-Chimonanthine, (-)-Folicanthine, and (+)-Calycanthine
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A general approach to bispyrroloindolines via a key thiourea-catalyzed addition of malonates to 3-sulfonyl-3′-indolyl-2-oxindoles is reported. The enantioselelective process is found to be highly effective (up to 94% ee), where a C-C bond formation leads
- Babu, K. Naresh,Roy, Avishek,Singh, Manvendra,Bisai, Alakesh
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supporting information
p. 6327 - 6331
(2018/10/20)
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- Cu(ii)-: TBu-PHOX catalyzed enantioselective malonate addition onto 3-hydroxy 2-oxindoles: Application in the synthesis of dimeric pyrroloindoline alkaloids
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An efficient Cu(ii)-PHOX-catalyzed malonate addition onto 3-hydroxy 3-indolyl-2-oxindoles is envisioned to afford excellent enantioselectivities (up to >99% ee) in high chemical yields. Detailed characterization techniques including X-ray, NMR, CV and EPR experiments suggest that a Cu(ii)-complex is involved as an active species in this process. Applying this strategy, an advanced intermediate of cyclotryptamine alkaloids has been synthesized in few steps for a general approach to bis-cyclotryptamine alkaloids.
- Babu, K. Naresh,Kinthada, Lakshmana K.,Pratim Das, Partha,Bisai, Alakesh
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supporting information
p. 7963 - 7966
(2018/07/25)
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- The first synthesis of cis-N,N′-dialkylisoindigo derivatives from 3-indolyl-2-oxindoles with DDQ
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cis-N,N′-Dialkylisoindigo derivatives were synthesized for the first time by the reaction of 3-indolyl-2-oxindoles with DDQ in aqueous 1,4-dioxane. cis-Isoindigo derivatives were completely isomerized to the corresponding trans-isomers by heating the solu
- Seo, Da Young,Roh, Hwa Jung,Jo, Hwi Yul,Cho, Sung,Kim, Jae Nyoung
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supporting information
p. 1005 - 1009
(2018/02/23)
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- Experimental and theoretical investigations of regioselective functionalization of 3-hydroxy bisindoles with thiols
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An instant and efficient p-TSA·H2O-catalyzed sulfenylation reaction of 3-hydroxy bisindole derivatives is reported. This highly regioselective approach afforded C-3 functionalized products in excellent yield, and this methodology was found to b
- Sharma, Nitika,Peddinti, Rama Krishna
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supporting information
p. 9259 - 9268
(2019/01/03)
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- FeCl3-Catalyzed Allylation Reactions onto 3-Hydroxy-2-oxindoles: Formal Total Syntheses of Bis-cyclotryptamine Alkaloids, (±)-Chimonanthine, and (±)-Folicanthine
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An FeCl3-catalyzed efficient strategy for the allylation reactions of 3-hydroxy-2-oxindoles with allyltrimethylsilane has been developed. The reaction affords a variety of 2-oxindoles having quaternary center at the pseudobenzylic position in an operationally simple and inexpensive procedure. Control experiments using enantioenriched 3-hydroxy-2-oxindole show that the reaction proceeds through in situ generated 2H-indol-2-one (8). The methodology presents an efficient and concise access to the pyrroloindoline alkaloids (±)-deoxyeseroline (1a), (±)-esermethole (1b), (±)-physostigmine (1c), (±)-phenserine (1d), and (±)-physovenine (1e). Eventually, we extrapolated the scope of this methodology to the formal total syntheses of dimeric cyclotyrptamine alkaloids (±)-chimonanthine (3a), (±)-folicanthine (3c), and (±)-calycanthine (4).
- Kinthada, Lakshmana K.,Medisetty, Sai Raghavendra,Parida, Amarchand,Babu, K. Naresh,Bisai, Alakesh
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p. 8548 - 8567
(2017/08/23)
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- Indole carbazole compounds and its preparation method and application
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The invention discloses an indole carbazole compound which is characterized by having a structure as shown in a formula I, a formula II, a formula III or a formula IV described in the specification. The indole carbazole has anti-TMV (tobacco mosaic virus) activity.
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Paragraph 0065; 0067
(2018/02/04)
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- Friedel-Crafts alkylation of indoles in deep eutectic solvent
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The application of Deep Eutectic Solvent (DES) as a solvent and a working catalyst for Friedel-Crafts alkylation of indoles with isatin as well as homocyclic carbonyl compounds has been developed. The salient features of the present protocol are practical simplicity, excellent yields, product selectivity and reusability of reaction media.
- Kumar, Atul,Shukla, Ratnakar Dutt,Yadav, Dhiraj,Gupta, Lalit Prakash
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p. 52062 - 52065
(2015/06/25)
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- Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5′ linkage via Friedel-Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindoles
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Simple and convenient Lewis acid-catalyzed Friedel-Crafts alkylations of 2-oxindoles as electron rich aromatics with 3-hydroxy-2-oxindoles as electron deficient partners have been developed. The reaction afforded a variety of dimeric 2-oxindoles with a C-
- Babu, K. Naresh,Kinthada, Lakshmana K.,Ghosh, Santanu,Bisai, Alakesh
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p. 10641 - 10655
(2015/11/17)
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- Catalytic Enantioselective Decarboxylative Allylations of a Mixture of Allyl Carbonates and Allyl Esters: Total Synthesis of (-)- and (+)-Folicanthine
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A highly enantioselective decarboxylative allylation of a mixture of enol carbonates and allyl esters has been achieved. The strategic viability of this methodology has been demonstrated through the total synthesis of cyclotryptamine alkaloids (-)- and (+)-folicanthine (1 a) and the formal total synthesis of (-)-chimonanthine (1 b), (+)-calycanthine (1 c), and (-)-ditryptophenaline (1 d).
- Ghosh, Santanu,Chaudhuri, Saikat,Bisai, Alakesh
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supporting information
p. 17479 - 17484
(2016/01/25)
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- "on water" expedient synthesis of 3-indolyl-3-hydroxy oxindole derivatives and their anticancer activity in vitro
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A series of 3-indolyl-3-hydroxy oxindole derivatives (n = 41) were synthesized by the green aminocatalytic method with excellent yields under mild reaction conditions. All the newly synthesized derivatives were subjected to evaluate their cytotoxic proper
- Sai Prathima, Parvathaneni,Rajesh, Pamanji,Venkateswara Rao, Janapala,Sai Kailash, Uppalapati,Sridhar, Balasubramanian,Mohan Rao, Mandapati
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supporting information
p. 155 - 159
(2014/07/22)
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- Kaolin/KOH is an efficient heterogeneous catalyst for the synthesis of 3-hydroxy-3-indolyl oxindoles
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3-Hydroxy-3-indolyl oxindoles were synthesized from isatins and indoles in good to excellent yields by using heterogeneous catalyst kaolin preloaded with KOH. Taylor & Francis Group, LLC.
- Srihari,Murthy, M. Marthanda
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experimental part
p. 2684 - 2692
(2011/08/05)
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- Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones under controlled catalysis of ionic liquids
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Three ionic liquids, [BMIM][BF4] doped with 60 mol % of LiCl ([BMIM][BF4]-LiCl), N,N,N,N-tetramethylguanidinium trifluoroacetate (TMGT), and N,N,N,N-tetramethylguanidinium triflate (TMGTf) were found useful as catalyst solvents for controlled 3-indolylation of isatins. Our investigation revealed that the reaction between isatin and indoles in [BMIM][BF4]-LiCl or TMGTf media stops at the step of addition of the two components providing 3-indolyl-3-hydroxyindolin-2-ones while the ionic liquid TMGT runs the reaction further through accompanying Friedel-Crafts substitution to afford symmetrical 3,3-di(indol-3-yl)indolin-2-ones. To take advantage of the difference between the effects of these ionic liquids on?the reaction progress, we planned a two-step protocol for the efficient synthesis of unsymmetrical 3,3-di(indol-3-yl)indolin-2-ones.
- Rad-Moghadam, Kurosh,Sharifi-Kiasaraie, Masoumeh,Taheri-Amlashi, Homayun
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body text
p. 2316 - 2321
(2010/06/12)
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- TREATMENT OF PROTEIN FOLDING DISORDERS
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In certain embodiments, the invention is directed to a method for treating a protein folding disorder such as Alzheimer's disease, dementia, Parkinson's disease, Huntington's disease and prion-based spongiform encephalopathy. The method comprises the administration to a subject of a compound of the formula (I) wherein A and B are independently a mono- or bicyclic aromatic group or heteroaromatic cyclic group. In preferred embodiments, the compounds are bis-indole compounds.
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Page/Page column 65
(2010/11/25)
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- Rebeccamycin analogues from indolo[2,3-c]carbazole
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Glycosylated indolocarbazoles related to the antibiotic rebeccamycin represent an important series of antitumor drugs. In the course of structure-activity relationship studies, we report the synthesis of two new derivatives containing an indolo[2,3-c]carb
- Voldoire, Aline,Sancelme, Martine,Prudhomme, Michelle,Colson, Pierre,Houssier, Claude,Bailly, Christian,Leonce, Stephane,Lambel, Stephanie
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p. 357 - 365
(2007/10/03)
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- Synthesis and resolution of 2,2'-bis-diphenylphosphino [3,3']biindolyl; a new atropisomeric ligand for transition metal catalysis
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A synthesis of the title ligand is described in which the key step is the dilithiation of 1,1'-bis(dimethylaminomethyl)-3,3'-biindolyl and electrophilic trapping with ClPPh2. Concomitant N-deprotection and resolution with bis[(R)-dimethyl(1-(1-naphthyl) ethylaminato-C2,N)palladium chloride] led to selective recovery of the S-enantiomer. The N-dimethylaminomethyl-substituted biindolyl, but not the parent compound, showed strongly second-order behaviour for 13C NMR peaks in the region of the phosphorus atom due to a desymmetrising 13C-induced isotope shift of the 31P resonance.
- Berens,Brown,Long,Selke
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p. 285 - 292
(2007/10/03)
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