- Selective Synthesis of Bis(indolyl)methanes under Solvent Free Condition Using Glucopyranosylamine Derived cis-Dioxo Mo(VI) Complex as an Efficient Catalyst
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cis-Dioxomolybdenum(VI) complex of 4,6-O-ethylidene-β-d-glucopyranosylamine derived ligand has been used as an efficient catalyst in the selective synthesis of a series of bis(indolyl)methanes (BIMs) by condensing indole derivatives with carbonyl compounds. The adopted synthetic procedure is green in nature as solvent free reactions have been carried out using naturally occurring d-glucose derived ligands. Total 15 BIMs have been synthesised including four new ones, which have been characterized by mp, FTIR, NMR and mass spectroscopy. The catalyst has afforded good to excellent yield of BIMs in short reaction time and the former has been recycled five times without any significant loss in it's catalytic efficiency.
- Baig, Noorullah,Shelke, Ganesh M.,Kumar, Anil,Sah, Ajay K.
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- Bis(indolyl)methane derivatives as highly selective colourimetric and ratiometric fluorescent molecular chemosensors for Cu2+ cations
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New probes based on bis(indolyl)methane derivatives only sense Cu2+ among other heavy and transition metal (HTM) ions through two different channels: the colourless to orange or purple colour change, that is visible to the naked eye, and a rema
- Martínez, Rosario,Espinosa, Arturo,Tárraga, Alberto,Molina, Pedro
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- Mechanism of the solvent-free reactions between indole derivatives and 4-nitrobenzaldehyde studied by solid-state NMR and DFT calculations
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In an effort to determine the details of the solid-state reaction mechanism of the Friedel-Crafts hydroxyalkylation between indole derivatives (indole, 1A, and N-methylindole, 1B) and an aromatic aldehyde (4-nitrobenzaldehyde), a series of solid-state NMR experiments have been performed. The reaction proceeds through a melted phase. By means of the DE pulse sequence the hydroxylic intermediate species (1H-indol-3-yl)(4- nitrophenyl)methanol (3A) and (1-methyl-1H-indol-3-yl)(4-nitrophenyl) methanol (3B) in the melt could be observed and characterized, providing evidence for elucidating the reaction mechanism. To support the experimental results, DFT calculations have been carried out showing that the first step of the reaction involving indole and nitrobenzaldehyde to give the intermediate 3A is energetically favored by 24.7 kJ mol-1, whereas the final product 3,3′-((4-nitrophenyl)methylene)bis(3a,7a- dihydro-1H-indole) (5A) is 54.8 kJ mol-1 lower in energy than the reactants. The calculated and experimental chemical shifts are also in good agreement providing further support to the proposed mechanism. This journal is
- Chierotti, Michele R.,Gaglioti, Katia,Gobetto, Roberto,Barbero, Margherita,Nervi, Carlo
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- Highly enantioselective Friedel-Crafts reaction of indoles with N-sulfonyl aldimines catalyzed by heteroarylidene malonate-type bis(oxazoline) copper(II) complexes
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The enantioselective Friedel-Crafts addition of indoles to N-sulfonyl aldimines was studied using a heteroarylidene malonate-type bis(oxazoline) as a chiral ligand. High to excellent enantioselectivities (up to >99% ee) were achieved using the complex of copper(II)-L1b with a benzyl group. The effects of ligand structure, solvent, temperature and substrate on the reaction were also investigated.
- Liu, Lei,Zhao, Qiuying,Du, Fengpei,Chen, Hongliang,Qin, Zhaohai,Fu, Bin
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- GO-Fe3O4-Ti(IV) as an efficient magnetic catalyst for the synthesis of bis(indolyl)methanes and benzo[a]xanthen-11-one derivatives
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In this study, a new and efficient magnetic composite was synthesized based on graphene oxide (GO). Initially, GO was coated with magnetite, and then Ti(IV) was fixed on GO-Fe3O4 via a covalent graft. The magnet
- Amiri-Zirtol, Leila,Amrollahi, Mohammad Ali,Mirjalili, Bibi-Fatemeh
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- Application of Magnetically Recoverable Core–Shell Nanocomposite in the Synthesis of Bis(indolyl)methanes at Room Temperature
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Abstract: A sulfonated polyethylene glycol-supported nano-magnetite (Fe3O4@PEG-SO3H) has been prepared, characterized, and evaluated as a magnetically recoverable core–shell nanocomposite catalyst for the synthesis of bis(
- Karimi-Jaberi, Z.,Mardani, Y.,Soltanian Fard, M. J.
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p. 1740 - 1747
(2021/12/13)
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- Bis-indolylation of aldehydes and ketones using silica-supported FeCl3: Molecular docking studies of bisindoles by targeting SARS-CoV-2 main protease binding sites
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We report herein an operationally simple, efficient and versatile procedure for the synthesis of bis-indolylmethanes via the reaction of indoles with aldehydes or ketones in the presence of silica-supported ferric chloride under grindstone conditions. The prepared supported catalyst was characterized by SEM and EDX spectroscopy. The present protocol has several advantages such as shorter reaction time, high yield, avoidance of using harmful organic solvents during the reaction and tolerance of a wide range of functional groups. Molecular docking studies targeted toward the binding site of SARS-CoV-2 main protease (3CLpro or Mpro) enzymes were investigated with the synthesized bis-indoles. Our study revealed that some of the synthesized compounds have potentiality to inhibit the SARS-CoV-2 Mpro enzyme by interacting with key amino acid residues of the active sites via hydrophobic as well as hydrogen bonding interactions.
- Deb, Barnali,Debnath, Sudhan,Chakraborty, Ankita,Majumdar, Swapan
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p. 30827 - 30839
(2021/11/19)
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- The novel acid-base magnetic recyclable catalyst prepared through carbon disulfide trapping process: Applied for green, one-pot, and efficient synthesis of 2,3-dihydroquinazolin-4 (1H) -ones and bis(indolyl)methanes in large-scale
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Herein, a nano acid-base catalyst using magnetic core and carbamodithioic acid functional group have been synthesized and characterized. Its efficiency in the synthesis of dihydroquinazolinones and bis(indolyl)methanes derivatives was investigated. This novel metal-free catalyst exhibited significant catalytic activity in both reactions under green and mild reaction conditions (the yield obtained for the first reaction products: 82–98 % and for the second one: 61–97 %). The catalyst displayed good recyclability with no significant loss of catalytic activity after eight runs (the conversion of the eighth run was found as 83 %, the fresh catalyst conversion was 95 %). The introduced approach is attractive due to its applicability in the large-scale synthesis of important medicinal compounds.
- Mohammadi Metkazini, Fatemeh,Khorsandi, Zahra,Heydari, Akbar
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- Halogen bond-catalyzed friedel-crafts alkylation of indole with ketones and aldehydes for the synthesis of symmetrical 3,3’-diindolylmethanes using simple halogen donor catalyst
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The Friedel-Crafts alkylation of indole with ketones and aldehydes had been developed to prepare 3,3’-diindolylmethanes using iodine or NCS as catalysts. Two mild and efficient catalysis systems were provided for the activation of carbonyl compounds and i
- Chen, Xia,Zhou, Xiao-Yu
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p. 604 - 610
(2021/09/30)
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- Solvent-free multi-component synthesis of unsymmetrical bis(indolyl)alkanes with Lewis acid-surfactant-SiO2 as nanocatalyst
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Herein we report the multicomponent synthesis of the bis(indolyl)methane derivatives in a ball mill. The reaction was carried out under solvent-free conditions using only the Lewis acid-surfactant-SiO2 composite nanocatalyst (LASSC) prepared in situ. The unsymmetrical bis(indolyl) methane derivatives containing nitro or fluorine substitution with a yield of 72%–92% were obtained in a short reaction time. Within we verified that under the action of the combined catalyst of AlCl3·6H2O + SDS + SiO2, the method of preparing unsymmetrical bis(indolyl)methane by mechanical grinding without solvent has obvious advantages. Finally, we inspected that the catalysis system can be used eight times without a significant decrease in activity.
- Wu, Zhiqiang,Wang, Gang,Li, Zhenliang,Feng, Enke,Liang, Yanping,Zhan, Haijuan,Liu, Wanyi
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supporting information
p. 1206 - 1217
(2021/02/01)
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- The impact of metal coordination on the assembly of bis(indolyl)methane-naphthalene-diimide amphiphiles
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The self-assembly and coordination of amphiphiles comprised of naphthalenediimide (NDI) and bis(indolyl)methane (BIM) chromophores were investigated as a function of pH and metal. As observed by TEM, SEM and AFM imaging, the self-assembly of NDI-BIM 1 pro
- Bayindir, Sinan,Lee, Kwang Soo,Parquette, Jon R.,Saracoglu, Nurullah
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supporting information
p. 13685 - 13692
(2020/10/26)
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- Simple iodoalkyne-based organocatalysts for the activation of carbonyl compounds
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A novel approach for the formation of bisindolylmethane derivatives (BIMs) is described as a proof of concept to evaluate the catalytic capacity of iodoalkynes. The use of these derivatives is reported as an example of simple halogen bond-based organocatalyst. This kind of activation has not been used before for the synthesis of bisindolylmethane derivatives 3. Interestingly, the preparation of 3-(1H-indol-3-yl)-1-phenylbutan-1-one (8) has been also achieved for the first time with an iodoalkyne derivative. We prove the efficiency of this family of new catalysts by developing a simple and easy operational methodology, opening the door to the development of alternative catalysts in the area of halogen bond-based organocatalysts.
- Alegre-Requena, Juan V.,Herrera, Raquel P.,Sonsona, Isaac G.,Uriel, Santiago,Valero-Tena, Alberto
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p. 1594 - 1601
(2020/03/06)
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- Heterogeneous SO3H@Fe3O4 magnetic nanocatalyst as an efficient and reusable medium for the synthesis of 3,3′-(arylmethylene)-bis-(4-hydroxycoumarin), bis-(indolyl)-methane, and 1,8-dioxo-octahydroxanthene derivatives
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This work aimed to synthesize a new heterogeneous catalyst (SO3H@Fe3O4 magnetic nanoparticles) and the study of its catalytic behavior in synthesizing 3,3′-(arylmethylene)-bis-(4-hydroxycoumarin), bis-(indolyl)-methane, an
- Wu, Xiaobo,Peng, Wan-Xi
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p. 2129 - 2148
(2020/06/24)
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- Synthesis and Catalytic Application of Bimetallic and Trimetallic Magnetic Nanoalloys for the Preparation of Bis(indolyl)methanes
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Abstract: Some bimetallic and trimetallic magnetic nanoalloys based on cobalt, copper,and silver have been synthesized and used as and green catalysts for thepreparation of bis(indolyl)methanes through electrophilic substitution reactionof indole with car
- Boroujeni, K. P.,Farokhnia, A.,Kazemi, R.,Kheiri, F.,Kiani, K.,Shahrokh, M.
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p. 1823 - 1831
(2020/12/01)
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- Organocatalytic combinatorial synthesis of quinazoline, quinoxaline and bis(indolyl)methanes
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Aims and Objective: An efficient and practical procedure for the synthesis of heterocyclic compounds such as quinazolines, quinoxalines and bis(indolyl)methanes was developed using 3,5-bis(trifluoromethyl) phenyl ammonium hexafluorophosphate (BFPHP) as a novel organocatalyst. Materials and Methods: All of the obtained products are known compounds and identified by IR, 1HNMR, 13CNMR and melting points. Result: Various products were obtained in good to excellent yields under reaction conditions Conclusion: The BFPHP organocatalyst demonstrates a novel class of non-asymmetric organocatalysts, which has gained much attention in green chemistry.
- Badri, Rashid,Khaksar, Samad,Malamiri, Fatemeh,Tahanpesar, Elham
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- COMPOUNDS AND USES THEREOF
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A pharmaceutical composition is described herein, including an antimicrobial agent and a compound having Formula A, or Formula B. Methods of using the pharmaceutical compositions to treat microbial infection are also described.
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Paragraph 0223-0224
(2020/06/10)
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- Synthesis of bis(indolyl)methanes under dry grinding conditions, promoted by a Lewis acid-surfactant-SiO2-combined nanocatalyst
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An in situ developed Lewis acid-surfactant-SiO2-combined (LASSC) nanocatalyst was used, for the first time, as a green and effective promoting medium for the electrophilic activation of aldehydes under solvent-free and dry grinding conditions. The advantages of using the LASSC nanocatalyst include avoiding the generation of wastewater containing sodium dodecyl sulfate and the use of toxic reagents, excellent reusability of the catalyst, and obtaining a high yield of bis(indolyl)methanes.
- Wu, Zhiqiang,Wang, Gang,Yuan, Shuo,Wu, Dan,Liu, Wanyi,Ma, Baojun,Bi, Shuxian,Zhan, Haijuan,Chen, Xiaoyan
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supporting information
p. 3542 - 3546
(2019/07/10)
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- Bimetallic Metal Organic Frameworks as Magnetically Separable Heterogeneous Catalysts and Photocatalytic Dye Degradation
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A new bimetallic MOF (BMOF) has been synthesized using iron and zinc as inorganic metal nodes and 1,4-benzenedicarboxylic acid (BDC) as the organic linker molecule. BMOF was confirmed by single-crystal X-ray diffraction (SCXRD), X-ray photoelectron spectroscopy (XPS), transmission electron microscopy high-angle annular dark-field imaging (TEM-HAADF), field emission scanning electron microscopy energy-dispersive X-ray analysis (FESEM-EDX), vibrating sample magnetometry (VSM) and inductively coupled plasma mass spectrometry (ICP-MS) analysis. The synthesized BMOF shows excellent optical and magnetic properties. BMOF acts as a heterogeneous catalyst and shows high catalytic activity towards bis(indolyl)methane synthesis and photocatalytic degradation of methylene blue (MB) under visible-light illumination.
- Tiwari, Ashish,Sagara, Prateep Singh,Varma, Vicky,Randhawa, Jaspreet Kaur
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p. 136 - 141
(2019/02/07)
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- Development of an imidazole salt catalytic system for the preparation of bis(indolyl) methanes and bis(naphthyl)methane
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Imidazolium salts are shown to catalyze the rapid room temperature reaction of indoles or naphthol with aldehydes to provide bis(indolyl)methanes or bis(naphthol)methane in excellent yields and the reaction proceeds optimally in dichloromethane with no base additives. The reaction exhibits a broad substrate tolerance and occurs through nucleophilic activation of the indoles and naphthols through a cation–π interaction.
- Wang, Xu,Aldrich, Courtney C.
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- A facile iron-catalyzed dual C-C bond cleavage: An approach towards triarylmethanes
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A facile iron-catalyzed dual C-C bond cleaving reaction involving 1,3-dicarbonyl units along with electron-rich and sterically bulky arenes as efficient carbon-based leaving groups has been developed. The scope of the dual C-C bond breaking reaction was s
- Paul, Dipankar,Khatua, Snehadrinarayan,Chatterjee, Paresh Nath
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supporting information
p. 10056 - 10065
(2019/07/03)
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- Synthesis, anti-methicillin-resistant S. aureus (MRSA) evaluation, quantitative structure-activity relationship and molecular modeling studies of some novel bis-indoles as prospective MRSA pyruvate kinase
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Background: MRSA is a gram positive pathogen resistant to methicillin and other betalactam antibiotics, including penicillin, oxacillin, and declooxacillin. Statistical data suggest that as many as 19,000 people per year die from MRSA in the USA. Methods:
- El Sayed, Inhibitors Mardia T.,Sabry, Nermien M.,Hamdy, Nehal A.,Voronkov, Andrey,Ogungbe, Ifedayo V.,Balakin, Konstantin,Abdel-Aziz, Mohamed S.
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p. 336 - 346
(2018/04/20)
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- Two novel binuclear sulfonic-functionalized ionic liquids: Influence of anion and carbon-spacer on catalytic efficiency for one-pot synthesis of bis(indolyl)methanes
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Two new binuclear sulfonic-functionalized ionic liquids with four-carbon spacer were synthesized and their structures were characterized by FTIR, MS, 1H and 13C NMR; then some physical properties and pH of the aqueous solution of new
- Khaligh, Nader Ghaffari,Mihankhah, Taraneh,Johan, Mohd Rafie,Ching, Juan Joon
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p. 260 - 273
(2018/03/22)
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- Self-assembled alkyl imidazolium based organosilica as efficient support for sulfonic acid catalyst in the synthesis of bis(indolyl)methanes
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A novel sulfonic acid-containing hybrid organic–inorganic material with ionic liquid framework (IL-OS-SO3H) is prepared, characterized and applied as efficient catalyst for the synthesis of bis(indolyl)methanes. The IL-OS-SO3H was pr
- Norouzi, Meysam,Elhamifar, Dawood,Mirbagheri, Reza
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p. 229 - 235
(2018/08/21)
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- Synthesis and characterization of a Ni nanoparticle stabilized on Ionic liquid-functionalized magnetic Silica nanoparticles for tandem oxidative reaction of primary alcohols
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In this research, preparation of the magnetic nanoparticle, coating by a silica shell using (3-aminopropyl) triethoxysilane and synthesis of a novel sulfonic acid-substituted imidazolium-based ionic liquid onto the surface of these particles via a multi-component reaction, is described. The functionalized nanoparticles was loaded by Ni nanoparticles and characterized by means of techniques such as XRD, FTIR, SEM, EDX, TEM, TGA and ICP-OES. The nanostructures have spherical shapes that ranged in size from 80 to 100?nm. The catalytic activity of these nanoparticles was tested in aerobic oxidation of primary alcohols that showed good performance in the wide range of primary alcohols in water at mild reaction conditions. As a second step of this work, the tandem oxidative synthesis of alkylacrylonitriles and bisindolylmethanes were investigated using primary alcohols under oxidation conditions. This catalyst system can be recovered using external magnet and reused for five consecutive cycles without significantly less of its activity.
- Hosseinzadeh-Khanmiri, Rahim,Kamel, Yaser,Keshvari, Zahra,Mobaraki, Ahmad,Shahverdizadeh, Gholam Hossein,Vessally, Esmail,Babazadeh, Mirzaagha
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- A one-pot synthesis of 2,2′-disubstituted diindolylmethanes (DIMs) via a sequential Sonogashira coupling and cycloisomerization/C3-functionalization of 2-iodoanilines
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A Pd(ii)-Ag(i) catalyzed highly efficient synthesis of diindolylmethane has been developed. This transformation consists of a one-pot sequential Sonogashira coupling (and desilylation) followed by cycloisomerization/C3-functionalization of 2-iodoanilines.
- Kayet, Anirban,Singh, Vinod K.
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p. 6997 - 7007
(2017/09/01)
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- BiVO4-NPs: an efficient nano-catalyst for the synthesis of biscoumarins, bis(indolyl)methanes and 3,4-dihydropyrimidin-2(1H)-ones (thiones) derivatives
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BiVO4-NPs can be used as an efficient and reusable nano-catalyst for the promotion of the synthesis of biscoumarins, bis(indolyl)methanes and 3,4-dihydropyrimidin-2(1H)-ones (thiones) derivatives. The structures of the products were characteriz
- Shirini, Farhad,Lati, Monireh Pourghasemi
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- Efficient synthesis of bis(indolyl)methanes, bispyrazoles and biscoumarins using 4-sulfophthalic acid
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4-Sulfophthalic acid (4-H3SPA) solution 50?wt% in H2O has been effectively catalyzed the synthesis of a series of biologically relevant bis(indolyl)methanes by the electrophilic substitution of indole derivatives on aldehyde compound
- Banari, Hoda,Kiyani, Hamzeh,Pourali, Alireza
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p. 1635 - 1649
(2017/02/15)
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- Green and efficient synthesis of aryl/alkylbis(indolyl)methanes using Expanded Perlite-PPA as a heterogeneous solid acid catalyst in aqueous media
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Expanded Perlite-Polyphosphoric acid (EP-PPA) as a novel, efficient, recyclable and eco-benign heterogeneous catalyst has been applied for the green and rapid synthesis of aryl/alkylbis(indolyl)methanes, in water, in good to excellent yields. The catalyst
- Esmaielpour, Marzieh,Akhlaghinia, Batool,Jahanshahi, Roya
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p. 313 - 328
(2017/03/23)
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- Caffeine-H3PO4: a novel acidic catalyst for various one-pot multicomponent reactions
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Caffeine-H3PO4 along with caffeine-HClO4 and caffeine-HNO3 have been prepared and applied for one-pot preparation of bis(indolyl) methanes, 4,4′-(arylmethylene) bis(1H-pyrazol-5-ols), 3,3′-(arylmethylene) bis(4-hydroxycoumarins), 2,4,5-trisubstituted imidazoles, 1‐amidoalkyl‐2‐naphthols, and polyhydroquinolines. The catalysts were characterized using Fourier-transform infrared (FTIR) spectroscopy, 1H and 13C nuclear magnetic resonance (NMR), powder X-ray diffraction (PXRD) analysis, thermogravimetric analysis (TGA), and liquid chromatography (LC)–mass spectroscopy (MS) techniques. The results indicated high product yield, short reaction time, facile separation of catalyst, and easy work-up procedure, suggesting that caffeine-H3PO4 can be considered to be an efficient acidic catalyst for organic transformations.
- Saghanezhad, Seyyed Jafar,Sayahi, Mohammad Hosein,Imanifar, Iman,Mombeni, Mostafa,Deris Hamood, Sajedeh
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p. 6521 - 6536
(2017/10/06)
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- NaY Zeolite Functionalized by Sulfamic Acid/Cu(OAc)2 as a Novel and Reusable Heterogeneous Hybrid Catalyst in Efficient Synthesis of Bis, Tris, and Tetrakis(indolyl)methanes, 3,4-Dihydropyrimidin-2(1H)-ones, and 2-Aryl-1H-benzothiazoles
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An efficient acid-catalyzed synthesis of some bis, tris, and tetrakis(indolyl)methanes, 3,4-dihydropyrimidin-2(1H)-ones, and 2-aryl-1H-benzothiazoles is reported using NaY zeolite functionalized by sulfamic acid/Cu(OAc)2 (NaY zeolite-NHSO3
- Kazemi, Samira,Mobinikhaledi, Akbar,Zendehdel, Mojgan
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p. 764 - 776
(2017/07/25)
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- Fe3O4@SiO2 supported aza-crown ether complex cation ionic liquids: preparation and applications in organic reactions
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A series of aza-crown ether ionic liquids supported on magnetic Fe3O4@SiO2 core-shell particles were designed, synthesized and characterized by elemental analysis, TEM, TG and FT-IR. These new aza-crown ether complex cation ionic liquids were utilized as heterogeneous acidic catalysts in Friedel-Crafts alkylation and Hantzsch reaction in good yields under convenient reaction conditions. Moreover, these magnetic particle supported IL catalysts could be readily recovered by an external magnet and reused five times without obvious loss of activity.
- Li, Dandan,Wang, Jinyuan,Chen, Fengjuan,Jing, Huanwang
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p. 4237 - 4242
(2017/02/05)
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- Benzenesulfonic Acid: A Versatile Catalyst for the Synthesis of Bis(indolyl)methanes as Antioxidants
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The reaction of indoles with carbonyl compounds in the presence of 5?mol% benzenesulfonic acid in acetonitrile was performed to synthesize bis(indolyl)methane derivatives adopting conventional and ultrasonication methodologies. The reaction proceeded in s
- Simha, Pulla Reddy,Mangali, Madhu Sekhar,Kuppireddy Gari, Divya,Venkatapuram, Padmavathi,Adivireddy, Padmaja
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p. 2717 - 2724
(2017/09/26)
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- Ionic Liquid [DABCO-H][HSO4] as a Highly Efficient and Recyclable Catalyst for Friedel-Crafts Alkylation in the Synthesis of Bis(naphthol)methane and Bis(indolyl)methane Derivatives
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A simple and highly efficient approach to the synthesis of bis(naphthol)methane (BNM) and bis(indolyl)methane (BIM) derivatives has been developed. In the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO)-based ionic liquid catalysts, which are environmental friendly, inexpensive, and recyclable, the reaction afforded the corresponding products in good to excellent yields within short times under solvent-free conditions. The catalysts can be easily recovered and reused several times without significant loss in activity.
- Tong, Jun,Yang, Cheng,Xu
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p. 3559 - 3566
(2016/10/17)
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- Copper supported on MWCNT-guanidine acetic acid@Fe3O4: Synthesis, characterization and application as a novel multi-task nanocatalyst for preparation of triazoles and bis(indolyl)methanes in water
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The synthesis of a new supported copper (Cu) nanocatalyst, with highly dispersed particles, based on magnetic guanidine acetic acid (GAA) functionalized multi-wall carbon nanotubes (MWCNT), Cu/MWCNT-GAA@Fe3O4, is reported. The synthe
- Shaabani, Ahmad,Afshari, Ronak,Hooshmand, Seyyed Emad,Tabatabaei, Azadeh Tavousi,Hajishaabanha, Fatemeh
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p. 18113 - 18125
(2016/03/01)
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- An efficient synthesis of bis(indolyl) methanes and N,N′-alkylidene bisamides by Silzic under solvent free conditions
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An operationally simple and green method for the synthesis of a wide range of bis(indolyl)methanes, and N,N′-alkylidene bisamides under mild conditions, with excellent yields using Silzic, has been developed. This improved method furnishes in good yields bis(indolyl)methanes derivatives starting from indole and aldehydes, or ketones, and N,N′-alkylidene bisamides derivatives starting from acetamide and aldehydes. The catalytic system was reused up to three times with the same efficiency.
- Soliman, Hanan A.,Mubarak, Ahmed Y.,Elmorsy, Saad S.
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p. 353 - 356
(2016/03/16)
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- Synthesis and characterization of Polyindole and its catalytic performance study as a heterogeneous catalyst
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The catalytic performance study of polyindole as a heterogeneous catalyst is reported for the synthesis of 3,3'-arylmethylene-bis-1H-Indole derivatives using various substituted aldehydes and indole under reflux reaction condition with good to excellent y
- Chhattise, Prakash,Handore, Kalpana,Horne, Amit,Mohite, Kakasaheb,Chaskar, Atul,Dallavalle, Sabrina,Chabukswar, Vasant
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p. 467 - 475
(2016/03/16)
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- Cu-isatin schiff base complex supported on magnetic nanoparticles as an efficient and recyclable catalyst for the synthesis of bis(indolyl)methanes and bis(pyrazolyl)methanes in aqueous media
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Cu-isatin Schiff base supported on γ-Fe2O3as a new catalyst was synthesized and characterized by different methods such as SEM, TEM, XRD, TGA, FT-IR, ICP, VSM and CHN analysis. It was used as a reusable heterogeneous catalyst for the
- Sobhani, Sara,Asadi, Solmaz,Salimi, Mehri,Zarifi, Farzaneh
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p. 154 - 164
(2016/09/09)
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- C-C bond cleavage: Metal-free-catalyzed reaction of Betti bases with various heterocycles under microwave irradiation
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The reaction of Betti bases with various heterocycles in the presence of p-toluenesulphonic acid (PTSA) under microwave irradiation gives bis(heterocycle)methanes through benzyl transfer. The reaction proceeds via the cleavage of C-N bond followed by C-C
- Deb, Mohit L.,Saikia, B.-Shriya,Borah, Kongkona,Baruah, Pranjal K.
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supporting information
p. 1940 - 1946
(2016/11/25)
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- Micro-Cu4I4-MOF: Reversible iodine adsorption and catalytic properties for tandem reaction of Friedel-Crafts alkylation of indoles with acetals
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We report a convenient approach, the first of its kind, to construct a microscale non-metal@MOF composite catalytic host-guest system for an organic tandem reaction. The reported porous Cu4I4-MOF is able to reversibly adsorb molecula
- Zhu, Neng-Xiu,Zhao, Chao-Wei,Wang, Jian-Cheng,Li, Yan-An,Dong, Yu-Bin
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supporting information
p. 12702 - 12705
(2016/11/02)
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- The presence of the amine salt preparation Diindole methane derivative method (by machine translation)
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The invention discloses a method for preparing a bis (indolyl) methane derivative in the presence of an amine salt. According to the method, by taking the amine salt as a catalyst, indole or an indole derivative is reacted with aldehyde to obtain the bis
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Paragraph 0010; 0011; 0012; 0013; 0048; 0049; 0050; 0051
(2017/01/02)
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- Oleic acid: A benign Br?nsted acidic catalyst for densely substituted indole derivative synthesis
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Oleic acid was identified to catalyse bis(indolyl)methane and densely functionalized 4H-chromene, spirooxindole and spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivative synthesis in good to excellent yields. The synergy between Br?nsted acidity and surfa
- Ganesan, Asaithampi,Kothandapani, Jagatheeswaran,Nanubolu, Jagadeesh Babu,Ganesan, Subramaniapillai Selva
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p. 28597 - 28600
(2015/04/14)
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- Development of Br?nsted-lewis acidic solid catalytic system of 3-methyl-1-sulfonic acid imidazolium transition metal chlorides for the preparation of bis(indolyl)methanes
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Three new heterogeneous catalysts of 3-methyl-1-sulfonic acid imidazolium transition metal chlorides [Msim][X] (where X=[FeCl4]-, [ZnCl3]-,[CuCl2]-) were synthesized containing both Lewis and Br?nsted acidic sites. These s
- Gogoi, Pinky,Dutta, Arup Kumar,Sarma, Parishmita,Borah, Ruli
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p. 133 - 139
(2015/05/05)
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- Triethylbenzylammonium chloride as a useful and efficient catalyst for the alkylation of indole/substituted indoles in water: A comparative study between conventional and microwave irradiation
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A green and facile method for the alkylation of indole/substituted indole in water using a phase Transfer catalyst (Triethylbenzylammonium Chloride, TEBA) to synthesise bis-indolyl methanes (BIMs) and Michael addition of indole to α,β-unsaturated carbonyl compounds is reported. The substitution of indoles occurred exclusively at the 3-position and products of N-alkylation has not been observed. However, for 3-substituted indoles, reactions were found to occur at the 2-position. A comparative study between conventional heating and microwave irradiation has also been reported. A comparative study between conventional heating and microwave irradiation for the alkylation of indole/substituted indole in water using a phase transfer catalyst (Triethylbenzylammonium Chloride, TEBA) to synthesise bis-indolyl methanes (BIMs) and Michael addition of indole to α, β-unsaturated carbonyl compounds is reported.
- Tumtina, Shokip,Kathing, Chingrishon,Phucho, Ivulho Tovishe,Nongrum, Ridaphun,Myrboh, Bekington,Nongkhlaw, Rishanlang
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p. 321 - 327
(2015/05/20)
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- Development of Br?nsted-Lewis acidic solid catalytic system of 3-methyl-1-sulfonic acid imidazolium transition metal chlorides for the preparation of bis(indolyl)methanes
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Three new heterogeneous catalysts of 3-methyl-1-sulfonic acid imidazolium transition metal chlorides [Msim][X] (where X = [FeCl4]-, [ZnCl3]-, [CuCl2]-) were synthesized containing both Lewi
- Gogoi, Pinky,Dutta, Arup Kumar,Sarma, Parishmita,Borah, Ruli
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p. 133 - 139
(2015/05/04)
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- Fe+3-Montmorillonite K10, as effective, eco-friendly, and reusable catalyst for the synthesis of bis(1H-indol-3-yl)methanes under grinding condition
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Bis(indoyl)methanes have been synthesized via electrophilic reaction of indole and aldehydes in excellent yields under mild reaction conditions in the presence of Fe+3-montmorillonite K10 as catalyst. The catalyst can be recovered and recycled in subsequent reactions without any apparent loss of activity.
- Fekri,Nikpassand,Kohansal
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p. 2861 - 2866
(2016/02/18)
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- SiO2-Diphenic acid: An efficient and recyclable heterogeneous catalyst for one-pot synthesis of bis-(indolyl)methane derivatives in liquid phase
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An eco-friendly and expedient procedure for one-pot synthesis of bis-(indolyl)methane derivatives via electrophilic substitution reaction at C-3 position of indole with various aldehydes has been developed by using silica-diphenic acid as a novel heteroge
- Vaid,Gupta,Chambyal,Gupta
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p. 987 - 997
(2015/09/07)
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- A domino electro-oxidative synthesis of 3,3′-bis(indolyl)methane nanoparticles
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An effective route for electro-oxidative synthesis of 3,3′-bis(indolyl)methane nanoparticles has been described via a domino multi-component reaction between various alcohols and indole derivatives in an undivided cell under constant potential conditions in CH3CN at room temperature. The mechanistic aspect of this electro-oxidative condensation has also been studied by UV-Vis spectra and cyclic voltammograms. The nanostructure of the products has been confirmed by scanning electron microscopy. Graphical abstract: [Figure not available: see fulltext.]
- Nikoofar, Kobra,Ghanbari, Khadijeh
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p. 2021 - 2027
(2015/11/24)
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- New magnetic nanocomposites of ZrO2-Al2O 3-Fe3O4 as green solid acid catalysts in organic reactions
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A series of magnetic solid acid nano-catalysts were designed and prepared through a facile co-precipitate approach. The original nanocomposites ZrO 2-Al2O3-Fe3O4 were characterized by means of ICP-AES
- Wang, Anqi,Liu, Xiang,Su, Zhongxing,Jing, Huanwang
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- Synthesis of pharmacologically active bis(indolyl) and tris(indolyl) derivatives using chlorotrimethylsilane
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Chlorotrimethylsilane is found to be a comparatively fast and efficient catalyst for carrying out electrophilic substitution reactions of indoles with various aldehydes/ketones/triethylorthoformate, yielding excellent amount of bis(indolyl)methanes/tris(indolyl)methanes. The merits of this protocol are avoidance of any external energy source, minimal reaction time, simple and easy procedure and high yield under solvent free room temperature condition. The versatility of this method has been tested with various aldehydes/ketones and received satisfactory results. A simple, fast, efficient, cheap and versatile method for the synthesis of bis(indolyl)methanes and tris(indolyl)methanes under solvent free room temperature condition using chlorotrimethylsilane as a catalyst has been developed. Thus, we have demonstrated the utility of TMSCl not only as a protecting group but also as catalyst in electrophilic substitution reactions. Copyright
- Singh, Nongthombam G.,Kathing, Chingrishon,Rani, Jims W. S.,Nongkhlaw, Rishan L.
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p. 442 - 446
(2014/05/06)
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- Boron trifluoride supported on nano-SiO2: An efficient and reusable heterogeneous catalyst for the synthesis of bis(indolyl)methanes and oxindole derivatives
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Boron trifluoride supported on nano-SiO2 was used as an efficient and heterogeneous catalyst for the electrophilic substitution reaction of indole with various aromatic aldehydes and isatins in methanol to afford the corresponding bis(indolyl)m
- Saffar-Teluri, Ali
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p. 1061 - 1067
(2014/05/06)
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- An underrated cheap Lewis acid: Molecular bromine as a robust catalyst for bis(indolyl)methanes synthesis
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A discovery that inexpensive elemental bromine can act as a potent Lewis acid catalyst is disclosed. Under the catalysis of only 2 mol% of Br 2, indoles reacted rapidly with carbonyl compounds to give bis(indolyl)methanes with extremely high efficiency and wide substrate scope. Moreover, a Br2-catalyzed aqueous-phase reaction is also presented to further demonstrate the power of this novel catalyst.
- Liang, Deqiang,Huang, Wenzhong,Yuan, Lin,Ma, Yinhai,Ma, Jingmei,Ning, Deman
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- Tetramethyl guanidinium chlorosulfonate as a highly efficient and recyclable organocatalyst for the preparation of bis(indolyl)methane derivatives
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The synthesis and characterization of a novel superbase ionic liquid, tetramethylguanidinium chlorosulfonate, are described. The guanidine ionic liquid (GIL) was characterized by FT-IR and NMR spectroscopies, and wide-angle X-ray scattering techniques, as
- Kalla, Reddi Mohan Naidu,John, Johnson V.,Park, Huiju,Kim, Il
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- Tetramethyl guanidinium chlorosulfonate as a highly efficient and recyclable organocatalyst for the preparation of bis(indolyl)methane derivatives
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The synthesis and characterization of a novel superbase ionic liquid, tetramethylguanidinium chlorosulfonate, are described. The guanidine ionic liquid (GIL) was characterized by FT-IR and NMR spectroscopies, and wide-angle X-ray scattering techniques, as
- Kalla, Reddi Mohan Naidu,John, Johnson V.,Park, Huiju,Kim, Il
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supporting information
p. 55 - 59
(2014/12/10)
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