cas 33985-68-1, 3,3'-((4-Methoxyphenyl)Methylene)bis(1H-indole)

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Well-Defined NNS-Mn Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Using Alcohols
Herein, we demonstrated Mn-catalyzed selective C-3 functionalization of indoles with alcohols. The developed catalyst can also furnish bis(indolyl)methanes from the same set of substrates under slightly modified reaction conditions. Mechanistic studies reveal that the C-3 functionalization of indoles is going via a borrowing hydrogen pathway. To highlight the practical utility, a diverse range of substrates including nine structurally important drug molecules are synthesized. Furthermore, we also introduced a one-pot cascade strategy for synthesizing C-3 functionalized indoles directly from 2-aminophenyl ethanol and alcohol.
Dutta, Bishal,Mondal, Avijit,Pal, Debjyoti,Sharma, Rahul,Srimani, Dipankar
supporting information
p. 3989 - 4000
(2022/03/27)

GO-Fe3O4-Ti(IV) as an efficient magnetic catalyst for the synthesis of bis(indolyl)methanes and benzo[a]xanthen-11-one derivatives
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
(2021/10/08)

Phosphine-Free Manganese(II)-Catalyst Enables Acceptorless Dehydrogenative Coupling of Alcohols with Indoles
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.
supporting information
p. 4430 - 4439
(2021/08/03)

Magnetically recyclable CuFe2O4 catalyst for efficient synthesis of bis(indolyl)methanes using indoles and alcohols under mild condition
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
(2020/11/30)

Chickpea leaf exudates: A green Br?nsted acid type biosurfactant for bis(indole)methane and bis(pyrazolyl)methane synthesis
A clean and highly efficient protocol for green synthesis of bis(indole)methanes and bis(pyrazolyl)methanes has been successfully achieved by using a naturally sourced bio-surfactant, chickpea leaf exudates (CLE), as a Br?nsted acid-type catalyst. The rea
Patil, Rupesh C.,Damate, Shashikant A.,Zambare, Dnyandev N.,Patil, Suresh S.
supporting information
p. 9152 - 9162
(2021/06/02)

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
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
p. 1517 - 1532
(2021/10/26)

Application of Magnetically Recoverable Core–Shell Nanocomposite in the Synthesis of Bis(indolyl)methanes at Room Temperature
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.
p. 1740 - 1747
(2021/12/13)

Bis-indolylation of aldehydes and ketones using silica-supported FeCl3: Molecular docking studies of bisindoles by targeting SARS-CoV-2 main protease binding sites
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
p. 30827 - 30839
(2021/11/19)

Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols
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
p. 2902 - 2910
(2020/06/03)

Metal-free oxidative coupling of arylmethylamines with indoles: A simple, environmentally benign approach for the synthesis of 3,3′-bis(indolyl)methanes
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.
p. 23254 - 23262
(2020/07/03)

COMPOUNDS AND USES THEREOF
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)

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
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
p. 2129 - 2148
(2020/06/24)

Synthesis and Catalytic Application of Bimetallic and Trimetallic Magnetic Nanoalloys for the Preparation of Bis(indolyl)methanes
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.
p. 1823 - 1831
(2020/12/01)

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
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
(2020/03/24)

A facile iron-catalyzed dual C-C bond cleavage: An approach towards triarylmethanes
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
supporting information
p. 10056 - 10065
(2019/07/03)

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
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.
supporting information
p. 4154 - 4159
(2019/11/14)

Iron-containing ionic liquid as an efficient and recyclable catalyst for the synthesis of C3-substituted indole derivatives
A facile and efficient protocol for the synthesis of C3-substituted indole derivatives has been developed under mild condition. The iron-containing ionic liquid, 1-(2-hydroxyethyl)-1,4-diazabicyclo[2.2.2] octanylium tetrachloroferrate ([Dabco-C2/sub
Gu, Ying-Chun,Hu, Ren-Ming,Li, Ming-Ming,Xu, Da-Zhen
(2019/01/19)

Phospho Sulfonic Acid: A Highly Efficient and Novel Catalyst for Formation of Bis(Indolyl)Alkanes from Aldehydes and Indole under Aqueous Conditions
Bis(indolyl)alkanes are a class of alkaloids that possess significant biological activities. Every year, the varieties of bis(indolyl)alkanes isolated from natural sources are increasing. Nevertheless, the deficiency of natural products from natural sourc
Faisal, Muhammad,Larik, Fayaz Ali,Salman, Muhammad,Saeed, Aamer
p. 522 - 535
(2019/09/04)

Synthesis of bis(indolyl)methanes under dry grinding conditions, promoted by a Lewis acid-surfactant-SiO2-combined nanocatalyst
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
supporting information
p. 3542 - 3546
(2019/07/10)

Halogen Bond-Catalyzed Friedel-Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes
The use of a halogen bond donor to catalyze Friedel-Crafts reactions of indoles with a range of aldehydes and ketones to directly produce bis(indolyl)methanes, including the natural products arsindoline A, arundine, trisindoline, and vibrindole A, is reported. The bidentate catalyst used in these reactions proved to be more effective than a monondentate analogue, a thiourea commonly used as an organocatalyst, and even a trityl cation that has been used previously in the synthesis of bis(indolyl)methanes.
Liu, Xuelei,Ma, Shuang,Toy, Patrick H.
supporting information
p. 9212 - 9216
(2019/11/14)

TEMPO/CuI synergetic catalyzed oxidative cross-coupling of indoles with benzylamines: Synthesis of bis(indolyl)phenylmethanes
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
supporting information
p. 1694 - 1700
(2018/06/15)

Synthesis and characterization of a Ni nanoparticle stabilized on Ionic liquid-functionalized magnetic Silica nanoparticles for tandem oxidative reaction of primary alcohols
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
(2018/08/06)

Method for preparing diindolyl methane derivative
The invention discloses a method for preparing a diindolyl methane derivative and belongs to the field of organic synthesis. The method comprises the following steps: by taking indole and aromatic aldehyde as reaction substrates, a sulfonic acid type ion
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Paragraph 0016; 0017

(2018/07/30)

A one-pot synthesis of 2,2′-disubstituted diindolylmethanes (DIMs) via a sequential Sonogashira coupling and cycloisomerization/C3-functionalization of 2-iodoanilines
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.
p. 6997 - 7007
(2017/09/01)

Base-promoted three-component cascade approach to unsymmetrical bis(indolyl)methanes
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.
supporting information
p. 1999 - 2003
(2017/04/27)

Exploration of Aberrant Behaviour of Grignard Reagents with Indole-3-carboxaldehyde: Application to the Synthesis of Turbomycin B and Vibrindole A Derivatives
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
supporting information
p. 117 - 121
(2016/12/26)

Catalytic properties of a cobalt metal-organic framework with a zwitterionic ligand synthesized: In situ
Herein we describe the high yield synthesis of a highly crystalline cobalt(ii) MOF with a novel zwitterionic ligand made up of 3,3′,4,4′-BPTC and 1,4-cyclohexanediamine, obtained in situ during the hydrothermal synthesis. The compound with the molecular f
Grigolo,De Campos,Manarin,Botteselle,Brand?o,Amaral,De Campos
p. 15698 - 15703
(2017/12/02)

Diindolylmethane Derivatives: Potent Agonists of the Immunostimulatory Orphan G Protein-Coupled Receptor GPR84
The Gi protein-coupled receptor GPR84, which is activated by (hydroxy)fatty acids, is highly expressed on immune cells. Recently, 3,3′-diindolylmethane was identified as a heterocyclic, nonlipid-like GPR84 agonist. We synthesized a broad range of diindolylmethane derivatives by condensation of indoles with formaldehyde in water under microwave irradiation. The products were evaluated at the human GPR84 in cAMP and β-arrestin assays. Structure-activity relationships (SARs) were steep. 3,3′-Diindolylmethanes bearing small lipophilic residues at the 5- and/or 7-position of the indole rings displayed the highest activity in cAMP assays, the most potent agonists being di(5-fluoro-1H-indole-3-yl)methane (38, PSB-15160, EC50 80.0 nM) and di(5,7-difluoro-1H-indole-3-yl)methane (57, PSB-16671, EC50 41.3 nM). In β-arrestin assays, SARs were different, indicating biased agonism. The new compounds were selective versus related fatty acid receptors and the arylhydrocarbon receptor. Selected compounds were further investigated and found to display an ago-allosteric mechanism of action and increased stability in comparison to the lead structure.
Pillaiyar, Thanigaimalai,K?se, Meryem,Sylvester, Katharina,Weighardt, Heike,Thimm, Dominik,Borges, Gleice,F?rster, Irmgard,Von Kügelgen, Ivar,Müller, Christa E.
p. 3636 - 3655
(2017/05/17)

Tris(hydroxymethyl)methane ammonium hydrogensulphate as a nano ionic liquid and its catalytic activity in the synthesis of bis(indolyl)methanes
In this study, tris(hydroxymethyl)methane ammonium hydrogensulphate [(THA)(HSO4)] was synthesized as the first nanoaliphatic ammonium-based ionic liquid via a simple chemical route in water. The [(THA)(HSO4)] ionic liquid was charact
Honarmand, Moones,Esmaeili, Elaheh
p. 741 - 749
(2016/12/30)

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
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
p. 764 - 776
(2017/07/25)

C-C bond cleavage: Metal-free-catalyzed reaction of Betti bases with various heterocycles under microwave irradiation
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.
supporting information
p. 1940 - 1946
(2016/11/25)

Micro-Cu4I4-MOF: Reversible iodine adsorption and catalytic properties for tandem reaction of Friedel-Crafts alkylation of indoles with acetals
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
supporting information
p. 12702 - 12705
(2016/11/02)

The presence of the amine salt preparation Diindole methane derivative method (by machine translation)
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; 0040; 0041; 0042; 0043

(2017/01/02)

Succinimidinium hydrogensulfate ([H-Suc]HSO4) as a new, green and efficient ionic liquid catalyst for the synthesis of tetrahydrobenzimidazo[2,1-b]quinazolin-1(2H)-one, 1-(benzothiazolylamino)phenylmethyl-2-naphthol, 1, 8-dioxo-octahydroxanthen
In this work, succinimidinium hydrogensulfate ([H-Suc]HSO4), a newly reported Br?nsted acidic ionic liquid, is used as an efficient and reusable catalyst in the synthesis of tetrahydrobenzimidazo[2,1-b]quinazolin-1(2H)-ones, 1-(benzothiazolylam
Goli-Jolodar, Omid,Shirini, Farhad
p. 1077 - 1092
(2016/05/02)

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
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
p. 321 - 327
(2015/05/20)

Iron-catalyzed oxidative coupling of benzylamines and indoles: Novel approach for synthesis of bis(indolyl)methanes
A novel route for synthesis of bis(indolyl)methanes has been developed by the oxidative coupling of benzylamines and indoles in the presence of iron(II) triflate as a catalyst and molecular oxygen as an oxidant. This method promises versatility, cost-effectiveness, and efficiency.
Gopalaiah, Kovuru,Chandrudu, Sankala Naga,Devi, Alka
p. 1766 - 1774
(2015/06/16)

A domino electro-oxidative synthesis of 3,3′-bis(indolyl)methane nanoparticles
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
p. 2021 - 2027
(2015/11/24)

Efficient, rapid, and solvent-free synthesis of substituted bis(indolyl)methanes using sulfated anatase titania as a solid acid catalyst
A rapid and solvent-free green synthesis of bis(indolyl)methanes using sulfated anatase titania (TiO2-SO42-) as solid acid catalyst under simple physical grinding has been developed. The advantage of this method is short reaction tim
Ravi,Krishnakumar,Swaminathan
p. 1380 - 1386
(2015/05/05)

Synthesis of bis(indolyl)methanes using ammonium niobium oxalate (ANO) as an efficient and recyclable catalyst
A green and efficient procedure was developed for the synthesis of bis(indolyl)methanes using ammonium niobium oxalate (ANO) NH4[NbO(C2O4)2(H2O)x]·nH2O as the catalyst and water
Mendes, Samuel R.,Thurow, Samuel,Penteado, Filipe,Da Silva, Mait S.,Gariani, Rogrio A.,Perin, Gelson,Lenardo, Eder J.
supporting information
p. 4334 - 4339
(2015/08/11)

BiCl3-loaded montmorillonite K10: A new solid acid catalyst for solvent-free synthesis of bis(indolyl)methanes
We report an efficient green process for synthesis of bis(indolyl)methane derivatives under solvent-free conditions by use of a new solid acid catalyst, BiCl3-loaded montmorillonite K10. The catalyst was characterized by SEM, BET surface area m
Ravi,Krishnakumar,Swaminathan
p. 5353 - 5364
(2015/07/08)

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
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
p. 133 - 139
(2015/05/05)

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
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
p. 133 - 139
(2015/05/04)

Convenient synthesis of bis(indolyl)alkanes by dithiocarbohydrazone Schiff base/Zn(ClO4)2·6H2O catalyzed Friedel-Crafts reaction of indoles with imines
A new, convenient and excellent yield procedure for the preparation of bis(indolyl)methanes (BIMs) by Friedel-Crafts reaction of indoles with imines in the presence of dithiocarbohydrazone Schiff base/Zn(ClO4) 2·6H2O as a
Hui, Yong-Hai,Chen, Yong-Cheng,Gong, Hai-Wei,Xie, Zheng-Feng
p. 163 - 165
(2014/02/14)

One-pot conversion of aromatic compounds to the corresponding bis(indolyl)methanes by the Vilsmeier-Haack reaction
Various electron-rich aromatics could be smoothly converted into the corresponding bis(indolyl)methanes in good to moderate yields by treatment of electron-rich aromatics with POCl3 and DMF, followed by treatment with indole at room temperature. The present article is the first report on a novel metal-free one-pot method for the preparation of bis(indolyl)methanes from electron-rich aromatics.
Veisi, Hojat,Ataee, Meral,Darabi-Tabar, Pegah,Amiri, Effat,Faraji, Ali Reza
p. 305 - 309
(2014/04/17)

Cooperative catalysis of silica gel with physisorbed water in the synthesis of bis(indolyl)alkanes
Silica gel catalyzed synthesis of bis(indolyl)alkane from the reaction of aldehyde and indole has been carried out. The fact that the reaction rate is slow with dried silica gel than that with moist silica gel suggest possible co-operative catalysis by water and silica gel to affect the transformation with excellent yield upon grinding at room temperature. This method for the synthesis of bis(indolyl)alkane has been found to be much better than many silica supported acid catalysts, since it requires no heating and has a much shorter reaction-time.
Bihani, Manisha,Bora, Pranjal P.,Askari, Hassan,Bez, Ghanashyam
p. 877 - 883
(2014/08/05)

Boron trifluoride supported on nano-SiO2: An efficient and reusable heterogeneous catalyst for the synthesis of bis(indolyl)methanes and oxindole derivatives
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
p. 1061 - 1067
(2014/05/06)

In situ generation of Iron(iii) dodecyl sulfate as Lewis acid-surfactant catalyst for synthesis of bis-indolyl, tris-indolyl, Di(bis-indolyl), Tri(bis-indolyl), tetra(bis-indolyl)methanes and 3-alkylated indole compounds in water
Iron(iii) dodecyl sulfate as Lewis acid-surfactant catalyst was prepared in situ and effectively used in the synthesis of bis(indolyl)methanes and Michael reactions of indoles with α,β-unsaturated carbonyl compounds in water. Also, this method was used for the synthesis of 1,1,3-tri-indolyl compounds, producing good to excellent yield at room temperature.
Veisi, Hojat,Maleki, Behrooz,Eshbala, Fereshteh Hosseini,Veisi, Hamed,Masti, Ramin,Ashrafi, Samaneh Sedigh,Baghayeri, Mehdi
p. 30683 - 30688
(2014/08/05)

Synthesis of pharmacologically active bis(indolyl) and tris(indolyl) derivatives using chlorotrimethylsilane
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.
p. 442 - 446
(2014/05/06)

Aza-crown ether complex cation ionic liquids: Preparation and applications in organic reactions
Aza-crown ether complex cation ionic liquids (aCECILs) were devised, fabricated, and characterized by using NMR spectroscopy, MS, thermogravimetric differential thermal analysis (TG-DTA), elemental analysis and physical properties. These new and room-temperature ILs were utilized as catalysts in various organic reactions, such as the cycloaddition reaction of CO2 to epoxides, esterification of acetic acid and alcohols, the condensation reaction of aniline and propylene carbonate, and Friedel-Crafts alkylation of indole with aldehydes were investigated carefully. In these reactions, the ionic liquid exhibited cooperative catalytic activity between the anion and cation. In addition, the aza-[18-C-6HK][HSO4]2 was the best acidic catalyst in the reactions of esterification and Friedel-Crafts alkylation under mild reaction conditions. Jewel in the crown: Nine new and room-temperature aza-crown ether complex ionic liquids (aCECILs) composed of multiple cations and anions were fabricated through a convenient procedure (see scheme). Some of them were used as catalysts in various organic reactions, such as the cycloaddition reaction of CO2 to propylene oxide, esterification of acetic acid and alcohols, the condensation of aniline and propylene carbonate, and Friedel-Crafts alkylation of indole with aldehydes.
Song, Yingying,Cheng, Chen,Jing, Huanwang
p. 12894 - 12900
(2015/03/30)

Synthesis of polyacrylonitrile fiber-supported poly(ammonium methanesulfonate)s as active and recyclable heterogeneous br?nsted acid catalysts
A new polyacrylonitrile fiber-supported Br?nsted acid catalyst has been developed and verified to efficiently (high yield, 10 cycles) mediate Biginelli reactions in ethanol, Pechmann condensations in toluene, Friedel-Crafts alkylations of indoles in water and conversion of fructose in dimethyl sulfoxide (DMSO) and mixed-aqueous system.
Shi, Xian-Lei,Xing, Xiaoli,Lin, Huikun,Zhang, Wenqin
supporting information
p. 2349 - 2354
(2014/07/21)