7501-91-9Relevant academic research and scientific papers
Selective Synthesis of Bis(indolyl)methanes under Solvent Free Condition Using Glucopyranosylamine Derived cis-Dioxo Mo(VI) Complex as an Efficient Catalyst
Baig, Noorullah,Shelke, Ganesh M.,Kumar, Anil,Sah, Ajay K.
, p. 333 - 337 (2016)
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.
Bis(indolyl)methane derivatives as highly selective colourimetric and ratiometric fluorescent molecular chemosensors for Cu2+ cations
Martínez, Rosario,Espinosa, Arturo,Tárraga, Alberto,Molina, Pedro
, p. 2184 - 2191 (2008)
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
Mechanism of the solvent-free reactions between indole derivatives and 4-nitrobenzaldehyde studied by solid-state NMR and DFT calculations
Chierotti, Michele R.,Gaglioti, Katia,Gobetto, Roberto,Barbero, Margherita,Nervi, Carlo
, p. 6732 - 6737,6 (2012)
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
Highly enantioselective Friedel-Crafts reaction of indoles with N-sulfonyl aldimines catalyzed by heteroarylidene malonate-type bis(oxazoline) copper(II) complexes
Liu, Lei,Zhao, Qiuying,Du, Fengpei,Chen, Hongliang,Qin, Zhaohai,Fu, Bin
, p. 1874 - 1878 (2011)
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.
Application of Magnetically Recoverable Core–Shell Nanocomposite in the Synthesis of Bis(indolyl)methanes at Room Temperature
Karimi-Jaberi, Z.,Mardani, Y.,Soltanian Fard, M. J.
, p. 1740 - 1747 (2021/12/13)
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(
Bis-indolylation of aldehydes and ketones using silica-supported FeCl3: Molecular docking studies of bisindoles by targeting SARS-CoV-2 main protease binding sites
Deb, Barnali,Debnath, Sudhan,Chakraborty, Ankita,Majumdar, Swapan
, p. 30827 - 30839 (2021/11/19)
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.
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
Mohammadi Metkazini, Fatemeh,Khorsandi, Zahra,Heydari, Akbar
, (2021/04/12)
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.
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
Chen, Xia,Zhou, Xiao-Yu
, p. 604 - 610 (2021/09/30)
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
GO-Fe3O4-Ti(IV) as an efficient magnetic catalyst for the synthesis of bis(indolyl)methanes and benzo[a]xanthen-11-one derivatives
Amiri-Zirtol, Leila,Amrollahi, Mohammad Ali,Mirjalili, Bibi-Fatemeh
, (2021/10/08)
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
Solvent-free multi-component synthesis of unsymmetrical bis(indolyl)alkanes with Lewis acid-surfactant-SiO2 as nanocatalyst
Wu, Zhiqiang,Wang, Gang,Li, Zhenliang,Feng, Enke,Liang, Yanping,Zhan, Haijuan,Liu, Wanyi
supporting information, p. 1206 - 1217 (2021/02/01)
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.
