- Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones
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Lanthanide triflates were found to be effective catalysts for reactions of indoles with aldehydes or ketones in aqueous solution.
- Chen, Depu,Yu, Libing,Wang, Peng George
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Read Online
- Trinuclear Lanthanide Coordination Clusters: Single-Molecule-Magnet Behavior and Catalytic Activity in the Friedel-Crafts Alkylation Reaction
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A new multidentate ligand (H3L) was synthesized by the condensation reaction of 4-tert-butyl-2,6-diformylphenol and 2-amino-4-nitrophenol. The reaction of the ligand with hydrated lanthanide nitrate produced two isostructural trinuclear coordin
- Sarkar, Arijit,Gómez-García, Carlos J.,Benmansour, Samia,Nayek, Hari Pada
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Read Online
- Highly enantioselective Friedel-Crafts reaction of indoles with imines by a chiral phosphoric acid
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Highly enantioselective Friedel-Crafts reactions of indoles with imines catalyzed by a chiral phosphoric acid are developed, affording the 3-indolyl methanamine derivatives with up to >99% ee for a wide range of substrates. Copyright
- Kang, Qiang,Zhao, Zhuo-An,You, Shu-Li
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Read Online
- A mild and environmentally friendly scandium(III) trifluoromethanesulfonate-catalyzed synthesis of bis(3′-indolyl)alkanes and bis(3′-indolyl)-1-deoxyalditols
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Bis(3′-indolyl)alkanes and bis(3′-indolyl) derivatives containing a 1-deoxyalditol moiety were synthesized in the presence of 5 mol % of scandium(III) trifluoromethanesulfonate [Sc(OTf)3] in CH 3CN or EtOH-H2O mixture as a
- Sato, Shingo,Sato, Toshihiro
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Read Online
- Novel method for synthesis of unsymmetrical bis(indolyl)alkanes catalyzed by ceric ammonium nitrate (CAN) under ultrasonic irradiation
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The reaction of indole with (1H-indol-3-yl)(alkyl) methanol was catalyzed efficiently by ceric ammonium nitrate under ultrasonic irradiation to afford the unsymmetrical bis(indolyl)alkane in good to excellent yields.
- Zeng, Xiao-Fei,Ji, Shun-Jun,Wang, Shun-Yi
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Read Online
- N-H...π(indole) intermolecular interactions in 3,3′-benzylidenediindole
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In molecules of the title compound, C23H18N2, two indole systems and one phenyl ring are connected through a common C atom. The two indole substituents are mutually orthogonal. We have identified two N - H...π(indole) inte
- Krishna,Velmurugan,Babu,Perumal
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Read Online
- Solvent-free indoles addition to carbonyl compounds promoted by CeCl 3·7H2O-NaI-SiO2: An efficient method for the synthesis of streptindole
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Efficient electrophilic substitution reactions of indoles with various carbonyl compounds proceed easily in solvent-free conditions using CeCl 3·7H2O-NaI-SiO2. system promoter, to afford the corresponding bis(1H-indol-3-yl
- Bartoli, Giuseppe,Bosco, Marcella,Foglia, Gioia,Giuliani, Arianna,Marcantoni, Enrico,Sambri, Letizia
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Read Online
- Triarylmethyl Cation-Catalyzed Three-Component Coupling for the Synthesis of Unsymmetrical Bisindolylmethanes
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An efficient synthesis of unsymmetrical bisindolylmethanes has been accomplished using triarylmethyl cations to catalyze the reaction of N-arylimines with two different indoles. Optimization of the organocatalyst by tuning cation stability allows for excellent single addition selectivity when coupled with p-nitrophenyl imines. The optimal catalyst is commercially available, and the reaction minimizes waste and environmental impact by employing a one-to-one ratio of starting materials. The intermediates can be isolated or used in situ in a one-pot two-step reaction to generate unsymmetrical bisindolylmethanes in high yields. The reaction tolerates a broad range of imines with the highest yields observed for electron-poor and neutral imines. A wide range of indole nucleophiles are also successfully employed allowing for the creation of a large variety of unsymmetrical bisindolylmethanes.
- Bardelski, Kevin,Brindle, Cheyenne S.,Chen, Zhenghua,Guarino-Hotz, Melissa,Jones, Vanessa A.,Lucas, Kelly,Patterson, William J.
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p. 6737 - 6742
(2021/12/31)
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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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- Sulfonated Tetraphenylethylene-Based Hypercrosslinked Polymer as a Heterogeneous Catalyst for the Synthesis of Symmetrical Triarylmethanes via a Dual C-C Bond-Cleaving Path
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A sulfonic acid functionalized tetraphenylethylene-based hypercrosslinked polymer (THP-SO 3H) with a well-developed porous network and accessible sulfonic acid sites was synthesized and characterized by different analytical techniques. The cata
- Kalita, Gitumoni,Deka, Namrata,Paul, Dipankar,Thapa, Loknath,Dutta, Gitish K.,Chatterjee, Paresh Nath
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supporting information
p. 304 - 308
(2020/12/14)
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- Facile access to bis(indolyl)methanes by copper-catalysed alkylation of indoles using alcohols under air
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Bis(3-indolyl)methanes (BIM) are important and present in the structure of many alkaloid and bioactive compounds (anti-inflammatory, anticancer, antiobesity, antimicrobial, etc.). Herein, we have reported an air stable and convenient Cu(OAc)2 c
- Nguyen, Ngoc-Khanh,Tran, Duc Long,Hung, Tran Quang,Le, Tra My,Son, Nguyen Thi,Trinh, Quang Thang,Dang, Tuan Thanh,Langer, Peter
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supporting information
(2021/03/15)
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- Magnetically recyclable CuFe2O4 catalyst for efficient synthesis of bis(indolyl)methanes using indoles and alcohols under mild condition
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Bis(3-indolyl)methanes (BIM) are highly valuable and appear in the core structure of many natural products and pharmacologically active compounds (anticancer, anti-inflammatory, antiobesity, antimetastatic, antimicrobial, etc.). Herein, we have disclosed
- Bui, Hoang Yen,Dang, Tuan Thanh,Ha, Minh-Tuan,Hung, Tran Quang,Nguyen, Ngoc-Khanh,Nguyen, Van Tuyen,Tran, Bich Ngoc,Trinh, Quang Thang,Vu, Xuan Hoan
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- Phosphine-Free Manganese(II)-Catalyst Enables Acceptorless Dehydrogenative Coupling of Alcohols with Indoles
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Herein, an air-stable, molecularly defined NNN?Mn(II) pincer complex catalyzed acceptorless dehydrogenative coupling of alcohols with indoles is reported. A wide variety of symmetrical and unsymmetrical bis(indolyl)methane derivatives as well as some structurally important products such as Vibrindole A, Turbomycin B alkaloid, Antileukemic, and Anticancer agents were synthesized. Mechanistic studies illustrate the importance of the NH moiety in the complex and the crucial role of metal-ligand cooperation during catalysis. (Figure presented.).
- Yadav, Vinita,Balaraman, Ekambaram,Mhaske, Santosh B.
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supporting information
p. 4430 - 4439
(2021/08/03)
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- Synthesis of Bis(indolyl)methanes through an Alkylation Reaction of Indoles with Sodium Alkoxides
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We describe an alkylation reaction of indoles with sodium alkoxides for the synthesis of bis(indolyl)methanes. 1-Tetralone proved to be an efficient hydrogen acceptor, thus avoiding the use of precious transition metals such as Ru and Ir. This reaction features transitionmetal-free conditions, uses readily available starting materials, and can be conducted on a gram scale.
- Chen, Xue,Jin, Hongwei,Liu, Yunkui,Zhou, Bingwei
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- Application of alkaloid arundine and derivatives thereof in prevention and control of plant viruses and pathogenic bacteria
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The invention relates to an application of alkaloid arundine and derivatives thereof in control of plant virus pathogens. It is found that arundine and derivatives I-1 to I-25 thereof show good anti-plant virus pathogen activity for the first time, and can well inhibit 14 plant germs including tobacco mosaic virus (TMV), cucumber fusarium wilt, peanut brown spot, apple ring spot, wheat sheath blight, corn bipolaris maydis, watermelon anthracnose, fusarium moniliforme, tomato early blight, wheat gibberellic disease, rice blast, phytophthora capsici, sclerotium of rape, cucumber gray mold and rice sheath blight.
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Paragraph 0011; 0014-0015; 0025
(2021/07/01)
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- Preparation of G-CuO NPs and G-ZnO NPs with mallow leaves, investigation of their antibacterial behavior and synthesis of bis(indolyl)methane compounds under solvent-free microwave assisted dry milling conditions using G-CuO NPs as a catalyst
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In this study, biogenic copper and zinc oxide nanoparticles (G-ZnONPs and G-CuONPs) were synthesized by the green synthesis method using Malva parviflora L. (Millow) leaf extract and the obtained nanoparticles were characterized in detail with UV-Vis, FTIR, SEM, XRD. The antibacterial properties of the synthesized nanoparticles on gram-positive and gram-negative bacteria were investigated and it was found that the nanoparticles had high antimicrobial activity in the results of the experiments. With the obtained G-CuONPs, the synthesis of bis(indolyl)methanes with the "green" one-pot synthesis using microwave was achieved quickly and with high efficiency, and the thermal behavior of the obtained products was investigated.
- SULAK, Mine
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p. 1517 - 1532
(2021/10/26)
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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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- FeCl3·6H2O as a Mild Catalyst for Nucleophilic Substitution of Symmetrical Bis(indoyl)methanes
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In this paper, unsymmetrical bis(indolyl)methane (BIM) and 3-alkylindole derivatives are smoothly synthesized from symmetrical BIMs with a variety of nucleophiles including heteroaromatic/aromatic compounds, allylsilane and alkynylsilane. FeCl3·6H2O is found to be a mild and highly effective catalyst for this nucleophilic substitution reaction in which N-methyl-2-phenylindole behaves as a good leaving group in the Csp3-Csp2 bond cleavage reaction. The operational ease, nonexpensive and environmentally friendly catalyst, mild reaction conditions, broad functional group tolerance, and scalability of this reaction strategy are advantages of the present procedure.
- Chantana, Chayamon,Jaratjaroonphong, Jaray
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p. 2312 - 2327
(2021/02/09)
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- Metal–Organic Layers Hierarchically Integrate Three Synergistic Active Sites for Tandem Catalysis
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We report the design of a bifunctional metal–organic layer (MOL), Hf12-Ru-Co, composed of [Ru(DBB)(bpy)2]2+ [DBB-Ru, DBB=4,4′-di(4-benzoato)-2,2′-bipyridine; bpy=2,2′-bipyridine] connecting ligand as a photosensitizer and Co(dmgH)2(PPA)Cl (PPA-Co, dmgH=dimethylglyoxime; PPA=4-pyridinepropionic acid) on the Hf12 secondary building unit (SBU) as a hydrogen-transfer catalyst. Hf12-Ru-Co efficiently catalyzed acceptorless dehydrogenation of indolines and tetrahydroquinolines to afford indoles and quinolones. We extended this strategy to prepare Hf12-Ru-Co-OTf MOL with a [Ru(DBB)(bpy)2]2+ photosensitizer and Hf12 SBU capped with triflate as strong Lewis acids and PPA-Co as a hydrogen transfer catalyst. With three synergistic active sites, Hf12-Ru-Co-OTf competently catalyzed dehydrogenative tandem transformations of indolines with alkenes or aldehydes to afford 3-alkylindoles and bisindolylmethanes with turnover numbers of up to 500 and 460, respectively, illustrating the potential use of MOLs in constructing novel multifunctional heterogeneous catalysts.
- Quan, Yangjian,Lan, Guangxu,Shi, Wenjie,Xu, Ziwan,Fan, Yingjie,You, Eric,Jiang, Xiaomin,Wang, Cheng,Lin, Wenbin
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p. 3115 - 3120
(2020/12/09)
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- Green synthesis of bis-coumarin derivatives using Fe(SD)3 as a catalyst and investigation of their biological activities
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A convenient, practical, green, and environmentally friendly method was developed for the synthesis of biscoumarins and corresponding tetrakis products from the reaction of 4-hydroxycoumarin and various aldehydes. The bis-coumarins were synthesized in hig
- Mahmoodi, Nosrat O.,Jalalifard, Zeinab,Fathanbari, Ghanbari Pirbasti
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p. 172 - 182
(2019/07/03)
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- Metal-free oxidative coupling of arylmethylamines with indoles: A simple, environmentally benign approach for the synthesis of 3,3′-bis(indolyl)methanes
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The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant. The present reaction provides a novel route towards the synthesis of 3,3′-bis(indolyl)methanes in excellent yields of up to 95% via C-C and C-N bond formation. This attractive and environmentally friendly one-pot protocol is a simple procedure that features inexpensive acetic acid as the catalyst and molecular oxygen as the sole oxidant, and it supports a wide substrate scope with the good tolerance of functional groups.
- Kadu, Vikas D.,Chandrudu, Sankala Naga,Hublikar, Mahesh G.,Raut, Dattatraya G.,Bhosale, Raghunath B.
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p. 23254 - 23262
(2020/07/03)
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- Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols
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Herein, we presented Ru-SNS complex that serves as a useful catalyst for C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcohols catalysed by a Ru-complex via “borrowing hydrogen” strategy is reported. This protocol provides an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives. (Figure presented.).
- Biswas, Nandita,Sharma, Rahul,Srimani, Dipankar
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supporting information
p. 2902 - 2910
(2020/06/03)
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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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- Air-stable μ-oxo-bridged binuclear titanium(IV) salophen perfluorooctanesulfonate as a highly efficient and recyclable catalyst for the synthesis of bis(indolyl) methane derivatives
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An air-stable μ-oxo-bridged binuclear Lewis acid of titanium(IV) salophen perfluorooctanesulfonate [{Ti(salophen)H2O}2O][OSO2C8F17]2 (1) was successfully synthesized by the reaction of TiIV(salophen)Cl2 with AgOSO2C8F17 and characterized by different techniques such as IR, NMR and HRMS. TG-DSC analysis showed that this complex was thermally stable at 220 °C. Meanwhile, it exhibited good solubility in polar organic solvents and good ionic dissociation in CH3CN solution. Fluorescence spectra and Hammett indicator results indicated that the complex had relatively strong acidity. And it showed high catalytic efficiency for the synthesis of bis(indolyl) methane derivatives through Friedel-crafts reaction of aldehyde/ketone with indoles. Moreover, it can be reused five times with minimal changes in catalytic efficiency.
- Qiao, Jie,Gao, Shan,Wang, Lingxiao,Wei, Jiancong,Li, Ningbo,Xu, Xinhua
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supporting information
(2019/11/29)
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- 3-Amino-5-mercapto-1,2,4-triazole-functionalized Fe3O4 magnetic nanocomposite as a green and efficient catalyst for synthesis of bis(indolyl)methane derivatives
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A core–shell Fe3O4?silica magnetic nanocomposite functionalized with 3-amino-5-mercapto-1,2,4-triazole (Fe3O4/SiO2/PTS/AMTA) was prepared using Fe3O4 with silica layer, and its s
- Hajibabaei, Maryam,Senejani, Masumeh Abdoli,Shafiei, Fatemeh
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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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- CF3SO2Na-Mediated, UV-Light-Induced Friedel-Crafts Alkylation of Indoles with Ketones/Aldehydes and Bioactivities of Products
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A concise, one-step route to produce 3,3′-diindolylmethanes (DIMs) from simple indoles and ketones or aldehydes is reported. The key step is the ready formation of indole derivatives that involves the in situ conversion of CF3SO2Na r
- Yang, Tianbao,Lu, Huiai,Shu, Yixuan,Ou, Yifeng,Hong, Ling,Au, Chak-Tong,Qiu, Renhua
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supporting information
p. 827 - 831
(2020/02/04)
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- Dehydrogenation and α-functionalization of secondary amines by visible-light-mediated catalysis
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A visible-light-mediated process for dehydrogenation of amines has been described. The given protocol showed a broad substrate scope, mild reaction conditions and excellent results without the requirement of tedious purification. This process can be applied in one-pot functionalization of secondary amines with various nucleophiles through the cooperation of visible-light and Lewis acid catalysis, leading to the structurally varied essential components of biologically active molecules. In addition, Stern-Volmer studies and quenching experiments revealed the role of a catalyst and led to the proposed mechanism of this transformation.
- Bujok, Robert,Morawska, Paulina,Pawlowski, Robert,Stanek, Filip,Stodulski, Maciej
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p. 2103 - 2112
(2020/03/27)
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- Self-supported nickel nanoparticles on germanophosphate glasses: Synthesis and applications in catalysis
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The development of supported catalysts based on simple procedures without waste products and time-consuming steps is highly desirable. In this paper, self-supported nickel-based nanoparticles were obtained at the surface of the germanophosphate glasses by
- Lenz, Guilherme Felipe,Schneider, Rodrigo,Rossi De Aguiar, Kelen M. F.,Bini, Rafael A.,Chaker, Juliano Alexandre,Hammer, Peter,Botteselle, Giancarlo V.,Felix, Jorlandio F.,Schneider, Ricardo
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p. 17157 - 17164
(2019/06/24)
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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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- Gold(III)-Catalyzed Decarboxylative C3-Benzylation of Indole-3-carboxylic Acids with Benzylic Alcohols in Water
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A strategy for the gold(III)-catalyzed decarboxylative coupling reaction of indole-3-carboxylic acids with benzylic alcohols has been developed. This cascade reaction is devised as a straightforward and efficient synthetic route for 3-benzylindoles in moderate to excellent yields (50-93%). A Hammett study of the protodecarboxylation gives a negative ρ value, suggesting that there is a buildup of positive charge on the indole ring in the transition state. Furthermore, comparison of initial rates in H2O and in D2O reveals an observed kinetic solvent isotope effect (KSIE = 2.7). This simple protocol, which affords the desired products with CO2 and water as the coproducts, can be achieved under mild conditions without the need for base or other additives in water.
- Hikawa, Hidemasa,Kotaki, Fumiya,Kikkawa, Shoko,Azumaya, Isao
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p. 1972 - 1979
(2019/05/16)
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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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- Oxidative Coupling of Benzylamines with Indoles in Aqueous Medium to Realize Bis-(Indolyl)Methanes Using a Water-Soluble Cobalt Catalyst and Air as the Oxidant
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Oxidative coupling of benzylamines with indoles to bis-(indolyl)methanes (BIMs) was achieved using an inexpensive water-soluble cobalt complex, Co(bpb). The catalyst was found to be quite effective when air was used as the oxidant and water as solvent under mild reaction conditions. Aromatic amines were successfully converted to the corresponding BIMs with yields up to 85 %. We have successfully carried out a 1 gram scale reaction, and few pharmaceutically relevant compounds were also synthesised by this method in good yields. Control experiments have also been carried out to understand the possible reaction mechanism.
- Saini, Parul,Kumari, Pratishtha,Hazra, Susanta,Elias, Anil J.
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supporting information
p. 4154 - 4159
(2019/11/14)
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- Thiamine hydrochloride as a recyclable organocatalyst for the synthesis of bis(indolyl)methanes, tris(indolyl)methanes, 3,3-di(indol-3-yl)indolin-2-ones and biscoumarins
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Thiamine hydrochloride was identified as an eco-friendly organocatalyst for the synthesis of a broad range of bis(indolyl)methanes in good to excellent yields. Green chemistry matrix calculations showed high atom economy and a small E-factor for the reaction. Moreover, the simple and easy operational protocol using a small amount of thiamine hydrochloride (1 mol%) makes this procedure an alternative approach for this transformation industrially. This protocol was also extended to the synthesis of naturally occurring alkaloids such as tris(indolyl)methane, arundine, vibrindole A, 3,3-di(indol-3-yl)indolin-2-ones and biscoumarin derivatives.
- Mathavan, Sivagami,Kannan, Keerthana,Yamajala, Rajesh B. R. D.
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supporting information
p. 9620 - 9626
(2019/11/20)
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- L-Proline catalyzed domino Michael addition of N-substituted anilines
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Here we report L-proline catalyzed 3-component reaction of indoles, aldehydes and N-substituted anilines in water as solvent at room temperature for the synthesis of 3-(α,α-diarylmethyl)indoles. The reaction is in fact a Michael addition of N-substituted
- Deb, Mohit L.,Deka, Bhaskar,Rahman, Iftakur,Baruah, Pranjal K.
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supporting information
p. 4430 - 4433
(2018/11/23)
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- One-pot sequential multi-component reaction: Synthesis of 3-substituted indoles
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Here, we have developed a 3-component one-pot sequential approach to 3-substituted indoles. The main advantages of this process are step economy, reduced waste, and operational simplicity. The method involves in situ generation of 3-indolylalcohols from t
- Borpatra, Paran J.,Deka, Bhaskar,Rajbongshi, Basanta K.,Deb, Mohit L.,Baruah, Pranjal K.
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supporting information
p. 2074 - 2082
(2018/07/15)
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- TEMPO/CuI synergetic catalyzed oxidative cross-coupling of indoles with benzylamines: Synthesis of bis(indolyl)phenylmethanes
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TEMPO/CuI was found to be an effective catalyst for the cross-coupling of indoles with benzylic amines affording the corresponding bis(indolyl)phenylmethanes under air atmosphere at room temperature in good to excellent yields. The efficiency, easy workup, simplicity, and chemoselectivity of this protocol provide a green and low-cost procedure for the synthesis of these compounds.
- Liao, Meixiang,Zhang, Xiaoyun,Yue, Pengfei
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supporting information
p. 1694 - 1700
(2018/06/15)
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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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- 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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- Palladium-catalyzed carbonylative bis(indolyl)methanes synthesis with TFBen as the CO source
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An efficient and convenient palladium-catalyzed carbonylative procedure for the synthesis of bis(indolyl)methanes has been established for the first time. With TFBen (benzene-1,3,5-triyl triformate) as the solid CO source, aryl iodides and indoles were tr
- Qi, Xinxin,Ai, Han-Jun,Zhang, Ning,Peng, Jin-Bao,Ying, Jun,Wu, Xiao-Feng
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- K2S2O8 -Activated Friedel-Crafts Type Alkylation of Indoles with α-Amido Sulfones
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A K 2 S 2 O 8 -activated regioselective alkylation of α-amido sulfones at the C-3 position of indoles is reported. The protocol developed herein provides an alternative new strategy to the previous approach by using Lewis acid, clay, and resin as catalyst for this Friedel-Crafts type alkylation of indoles with α-amido sulfones. The formed product bears a versatile transformable sulfone group and an amino group. The reaction condition is tolerant to a wide range of substrates, including a series of indoles with electron-withdrawing and electron-donating groups at different positions. Moreover, a variety of α-substituted phenylamido sulfones and some α-aliphatic amido sulfones also give the desired products in modest yield. Furthermore, a preliminary mechanism study was performed and the plausible reaction mechanism is discussed.
- Wu, Xiaoyan,Xue, Lu,Luo, Shilong,Jia, Shiqi,Ao, Jun,Qin, Wenling
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p. 5017 - 5024
(2017/10/06)
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- Divergent dehydrogenative coupling of indolines with alcohols
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The dehydrogenative coupling of indolines with alcohols catalyzed by an iridium complex has been achieved to afford both N- and C3-alkylated indoles selectively, by simply changing the addition time of a base additive. The iridacycle catalyst plays multiple roles in these reactions, which dehydrogenates both amines and alcohols and catalyzes the coupling reactions. Mechanistic studies reveal that a borrowing hydrogen-dehydrogenation process and a dehydrogenationborrowing hydrogen process are involved in N-alkylation and C3-alkylation reactions, respectively. The C3-alkylation reaction involves the direct coupling of two sp3 carbon centers.
- Jiang, Xue,Tang, Weijun,Xue, Dong,Xiao, Jianliang,Wang, Chao
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p. 1831 - 1835
(2017/08/01)
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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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- Base-promoted three-component cascade approach to unsymmetrical bis(indolyl)methanes
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Here we report a base-catalyzed reaction of two different indoles with aldehydes under heating to produce unsymmetrical bis(indolyl)methanes (BIMs), in which one of the indole ring must be N-substituted. Mixture of EtOH-H2O is used as solvent. The reaction did not give symmetrical BIMs of N-substituted indoles or N–H indoles. However, traces of latter were formed in few cases, especially when electron-rich aldehydes were used. Diversely substituted indoles and aldehydes were used for the reaction. The reaction proceeds via 3-indolylalcohol, which we confirmed through isolation. The method also gives good yield on multigram scale reaction.
- Deb, Mohit L.,Deka, Bhaskar,Saikia, Prakash J.,Baruah, Pranjal K.
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supporting information
p. 1999 - 2003
(2017/04/27)
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- Pyridylmethylamine–Palladium Catalytic Systems: A Selective Alternative in the C?H Arylation of Indole
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A highly efficient pyridylmethylamine-Pd alternative catalytic system for the C?H arylation of indole was explored. Variously substituted aryl groups were regio- and chemoselectively installed at the indole nucleus by using barium hydroxide as the base. The method was found to be efficient even in the presence of hindered coupling partners and Pd-reactive bonds.
- Perato, Serge,Large, Benjamin,Lu, Qiao,Gaucher, Anne,Prim, Damien
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p. 389 - 392
(2017/02/15)
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- Exploration of Aberrant Behaviour of Grignard Reagents with Indole-3-carboxaldehyde: Application to the Synthesis of Turbomycin B and Vibrindole A Derivatives
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An aberrant reaction of Grignard reagents with N-alkylated indole-3-carboxaldehyde has been observed. Contrary to the usual formation of an alcohol, it afforded an unusual bis(indolyl)methane product. A systematic study on this new mode of reactivity and its application to a synthesis of the potent antibiotic turbomycin B and vibrindole A derivatives is reported.
- Bahuguna,Sharma,Sagara,Ravikumar
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supporting information
p. 117 - 121
(2016/12/26)
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- Iron-Catalyzed Direct C3-Benzylation of Indoles with Benzyl Alcohols through Borrowing Hydrogen
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We present the coupling of primary and secondary benzyl alcohols with indoles to form 3-benzylated indoles and H2O that is catalyzed, for the first time, by a complex of earth-abundant iron. This transformation accommodates a variety of substrates and is distinguished by its operational simplicity, sustainability, high functional-group tolerance, and amenability to gram-scale synthesis. On the basis of the preliminary experimental observations, we propose that the reaction proceeds through a borrowing hydrogen process.
- Di Gregorio, Giovanni,Mari, Michele,Bartoccini, Francesca,Piersanti, Giovanni
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p. 8769 - 8775
(2017/08/23)
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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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- 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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- 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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- Gold-catalyzed oxidative couplings of two indoles with one aryldiazo cyanide under oxidant-free conditions
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Gold-catalyzed oxidative couplings of two indoles and one α-cyano gold carbene to form bis(indolyl)methane derivatives are described. Two different indoles are compatible with these reactions to provide reasonable yields. A plausible mechanism is postulated to rationalize the experimental data including product distributions, D2O labeling, and the significant effects of gold catalysts and cyano groups.
- Singh, Rahulkumar Rajmani,Liu, Rai-Shung
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p. 4593 - 4596
(2017/04/28)
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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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- Catalyst-free synthesis of 3-(1-arylsulfonylalkyl)indoles via three-component reaction of indoles, carbonyls, and arenesulfinic acids
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A catalyst-free three-component reaction of indoles, carbonyls, and arenesulfinic acids performed at room temperature provides direct access to biologically important 3-(1-arylsulfonylalkyl)indoles. This process features mild conditions, low cost, broad s
- Huang, Wenzhong,Yang, Juan,Li, Xiangguang,Yuan, Lin,Ma, Yinhai,Zhou, Qinglong,Liang, Deqiang
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p. 772 - 777
(2016/05/09)
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- Br?nsted-Acid-Mediated Divergent Reactions of Betti Bases with Indoles: An Approach to Chromeno[2,3-b]indoles through Intramolecular Dehydrogenative C2-Alkoxylation of Indole
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Divergent reactions of various 1-(aminoalkyl)naphthols and 2-(aminoalkyl)phenols (commonly known as Betti bases) with indoles under Br?nsted acid catalysis is reported. With the reaction strategies, one can efficiently synthesize important indole derivatives such as 3-(α,α-diarylmethyl)indoles and chromeno[2,3-b]indoles. Furthermore, we disclose here a new C–C bond-cleavage reaction, in which naphthol and phenol behave as leaving groups to produce diarylmethanes. Inexpensive reagents such as p-toluenesulfonic acid monohydrate and molecular iodine are used to catalyze the reactions. No metal catalyst is required. The starting material of the reactions, Betti bases, are easily prepared from a three-component reaction of naphthol/phenol, aldehydes, and secondary amines. The mechanisms for the reactions are established through some control experiments. Quinone methide is the key intermediate for all the reactions reported herein.
- Deb, Mohit L.,Pegu, Choitanya Dev,Deka, Bhaskar,Dutta, Prantu,Kotmale, Amol S.,Baruah, Pranjal K.
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p. 3441 - 3448
(2016/07/23)
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- ‘Naked-eye’ colorimetric/fluorimetric detection of F? ions by biologically active 3-((1H-indol-3-yl)methyl)-4-hydroxy-2H-chromen-2-one derivatives
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An improved synthetic protocol has been developed for the construction of highly functionalized heterologous alkyl and benzyl indolyl-coumarin derivatives through a rapid, catalyst-free and solvent-free one-pot three-component reaction of indole, aldehyde
- Shaily,Kumar, Ajay,Kumar, Sumit,Ahmed, Naseem
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p. 108105 - 108112
(2016/11/28)
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- Tunable titanocene lewis acid catalysts for selective friedel-crafts reaction of indoles and N-sulfonylaldimines
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A newc strategy to control the selective Friedel-Crafts reaction of indoles and imines under mild conditions was developed. Phenol derivatives were established as efficient ligands to finely tune the activity of titanocene dichloride. Cp2TiCl2 and phenol catalyzed the mono-Friedel-Crafts reaction of indoles and N-sulfonyl aldimines with good yields (91 %), whereas o-aminophenol significantly enhanced the activity of the titanocene catalyst and promoted the synthesis of bisindole with excellent yields (98 %). The new organometallic Lewis acid catalysts are air-tolerant, can be used with low catalyst loading (3 mmol-%) and are compatible with -NO2, -F, -Cl, -Br, and -OMe (30 examples with yields from good to excellent). The titanocene catalysts were fully characterized by NMR and HRMS analysis. The results suggest that Cp2TiCl(OC6H5) (I) and Cp2TiCl(OC6H4NH3+Cl-) (II) were catalytic species for the mono- and double-Friedel-Crafts reactions, respectively. Distinguished from single functional acid catalysts I, catalyst II showed a catalytic cooperative effect of two acid components, which led to a fine tuning of the reactivity as well as to the selectivity of the desired reaction pathways. A Ti-catalyzed, highly selective Friedel-Crafts reaction of indoles and imines has been developed. Cp2TiCl2 and phenol, with a single Lewis acid site, catalyzed the mono-Friedel-Crafts reaction of indoles and N-sulfonylaldimines, whereas o-aminophenol enhanced the acidity of titancene catalyst, enabling both Lewis and Bronsted acid sites to promote the synthesis of bisindole.
- Xiu, Wang,Zhenhua, Wang,Zhang, Guofang,Zhang, Weiqiang,Wu, Ya,Gao, Ziwei
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supporting information
p. 502 - 507
(2016/02/18)
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