103608-21-5Relevant articles and documents
Regioselective Friedel-Crafts acylation of indoles catalysed by zinc oxide in an ionic liquid
Zhang, Li-Rong,Yi, Feng-Ping,Zou, Jian-Zhong,Zhang, Xuan,Wang, Zhen
, p. 600 - 602,3 (2012)
A facile method for the regioselective Friedel-Crafts acylation of indoles with acyl chlorides catalysed by zinc oxide in an ionic liquid medium has been developed. The corresponding 3-acylindoles were obtained in good to high yields under mild reaction conditions. Zinc oxide, which is easily available and requires no special handling procedures, is an efficient catalyst for acylation of indoles.
Preparation of magnetically recyclable MIL-53(Al)@SiO2@Fe3O4 catalysts and their catalytic performance for Friedel-Crafts acylation reaction
Jiang, Sai,Yan, Junlei,Habimana, Fabien,Ji, Shengfu
, p. 83 - 90 (2016)
Novel magnetically recyclable MIL-53(Al)@SiO2@Fe3O4 catalysts with different MIL-53(Al) contents were prepared by encapsulating magnetic SiO2@Fe3O4 nanoparticles into MIL-53(Al) through an in situ method. The structure of the catalysts was characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), Fourier transform infrared (FT-IR) spectroscopy, vibration sample magnetometer (VSM), and N2 adsorption/desorption techniques. Catalytic activity and recovery properties of the catalysts for Friedel-Crafts acylation reaction of 2-methylindole with benzoyl chloride were evaluated. The results showed that the magnetic MIL-53(Al)@SiO2@Fe3O4 catalysts have the larger surface areas, suitable superparamagnetism, and good catalytic activity for Friedel-Crafts acylation reaction. Over 38.8% MIL-53(Al)@SiO2@Fe3O4 catalyst under the reaction conditions of 25 °C for 8 h the conversion of 2-methylindole can reach ～98%, and the selectivity of 3-acetylindole and that of N-acetylindole can reach ～81% and ～18%, respectively. After the reaction, the catalyst can be easily separated from the reactant mixture by an external magnet. The recovered catalyst can be reused for five times, and the conversion of 2-methylindole can be kept over 90% and the selectivity of 3-acetylindole can be maintained at 80%.
Metal-organic framework MIL-53(Al): Synthesis, catalytic performance for the Friedel-Crafts acylation, and reaction mechanism
Yan, Junlei,Jiang, Sai,Ji, Shengfu,Shi, Da,Cheng, Hefei
, p. 1544 - 1552 (2015)
Metal-organic framework MIL-53(Al) was synthesized by a solvothermal method using aluminum nitrate as the aluminium source and 1,4-benzenedicarboxylic acid (H2BDC) as the organic ligand. The structure of samples was characterized by X-ray diffraction (XRD) and Fourier transform infrared spectroscopy (FT-IR). The catalytic activity and recyclability of MIL-53(Al) catalyst for the Friedel-Crafts acylation reaction of indole with benzoyl chloride were evaluated. The reaction conditions were optimized and a reaction mechanism was suggested. The results showed that the MIL-53(Al) catalyst exhibited good catalytic activity and recyclability for the Friedel-Crafts acylation reaction. When the molar ratio of indole and MIL-53(Al) catalyst was 1:0.06 (n 1:n catalyst), the molar ratio of indole and benzoyl chloride was 1:3, and the solvent was dichloromethane, the conversion of indole could reach 97.1% and the selectivity of 3-acylindole could reach 81.1% at 25 °C after 8 h. The catalyst can be reused without significant degradation in catalytic activity. After the catalyst was reused five times, the conversion of indole was 87.6% and the selectivity of 3-acylindole was 79.5%.
NbCl5 and AgClO4 promoted regio-selective acylation of indoles
Kamble, Narendra R.,Pawar, Hari R.,Kamble, Vinod T.
, p. 317 - 321 (2020/01/08)
In present study, an efficient and simple strategy towards chemo-selective and regio-selective acylation of indole using NbCl5 and AgClO4 catalyst are reported. This method utilizes the catalytic potentiality of NbCl5 and AgClO4 towards acylation of unprotected indoles in a synergistic manner. The combination of these catalytic system results into numerous advantages such as excellent yields of product, short reaction times and easier isolation of products.
A novel synthesis of N-hydroxy-3-aroylindoles and 3-aroylindoles
Ieronimo, Gabriella,Palmisano, Giovanni,Maspero, Angelo,Marzorati, Alessandro,Scapinello, Luca,Masciocchi, Norberto,Cravotto, Giancarlo,Barge, Alessandro,Simonetti, Marco,Ameta, Keshav Lalit,Nicholas, Kenneth M.,Penoni, Andrea
, p. 6853 - 6859 (2018/10/20)
A straightforward indole synthesis via annulation of C-nitrosoaromatics with conjugated terminal alkynones was realised achieving a simple, highly regioselective, atom- and step economical access to 3-aroylindoles in moderate to good yields. Further functionalizations of indole scaffolds were investigated and an easy way to JWH-018, a synthetic cannabinoid, was achieved.
