91805-61-7Relevant articles and documents
MnO2?Fe3O4 Magnetic Nanoparticles as Efficient and Recyclable Heterogeneous Catalyst for Benzylic sp3 C?H Oxidation
Pandey, Akanksha M.,Agalave, Sandip G.,Vinod, Chathakudath P.,Gnanaprakasam, Boopathy
, p. 3414 - 3423 (2019)
Herein, we report a highly chemoselective and efficient heterogeneous MnO2?Fe3O4 MNP catalyst for the oxidation of benzylic sp3 C?H group of ethers using TBHP as a green oxidant to afford ester derivatives in high yield under batch/continuous flow module. This catalyst was also effective for the benzylic sp3 C?H group of methylene derivatives to furnish the ketone in high yield which can be easily integrated into continuous flow condition for scale up. The catalyst is fully characterized by spectroscopic techniques and it was found that 0.424 % MnO2?Fe3O4 catalyzes the reaction; the magnetic nanoparticles of this catalyst could be easily recovered from the reaction mixture. The recovered catalyst was recycled for twelve cycles without any loss of the catalytic activity. The advantages of MnO2?Fe3O4 MNP are its catalytic activity, easy preparation, recovery, and recyclability, gram scale synthesis with a TOF of up to 14.93 h?1 and low metal leaching during the reaction.
Copper-mediated simple and direct aerobic oxidative esterification of arylacetonitriles with alcohols/phenols
Dong, Jianyu,Chen, Xiuling,Ji, Fangyan,Liu, Lixin,Su, Lebin,Mo, Min,Tang, Jian-Sheng,Zhou, Yongbo
, (2020/10/20)
A simple and direct aerobic oxidative esterification reaction of arylacetonitriles with alcohols/phenols is achieved in the presence of a copper salt and molecular oxygen, which produces a broad range of aryl carboxylic acid esters in good to high yields. Copper salt plays multiple roles in the transformation, which allows the oxygenation of C-H bond, cleavage of inert C-C bond, and formation of C-O bond in one pot without the assistance of any of the acids, bases, ligands, and so on. The reaction provides a simple, direct, and efficient protocol towards functionalized esters, especially aryl benzoates, from readily available starting materials.
Synthesis, characterization, docking study and antimicrobial activity of 2-(4-benzoylphenoxy)-1-[2-(1-methyl-1H-indol-3-yl)methyl)-1H-benzo[d]imidazol-1-yl] ethanone derivatives
Prashanth,Ranganatha, V. Lakshmi,Ramu, Ramith,Mandal, Subhankar P.,Mallikarjunaswamy,Khanum, Shaukath Ara
, p. 2741 - 2756 (2021/03/29)
The occurrence of drug-resistant bacterial infections impulses the development of new antibacterial agents that own a mechanism of action different from traditional antibiotics. From the earlier days, benzophenone, indole and benzimidazole moieties alone
Tropolonate salts as acyl-transfer catalysts under thermal and photochemical conditions: Reaction scope and mechanistic insights
Mai, Binh Khanh,Koenigs, Rene M.,Nguyen, Thanh Vinh,Lyons, Demelza J.M.,Empel, Claire,Pace, Domenic P.,Dinh, An H.
, p. 12596 - 12606 (2020/11/18)
Acyl-transfer catalysis is a frequently used tool to promote the formation of carboxylic acid derivatives, which are important synthetic precursors and target compounds in organic synthesis. However, there have been only a few structural motifs known to efficiently catalyze the acyl-transfer reaction. Herein, we introduce a different acyl-transfer catalytic paradigm based on the tropolone framework. We show that tropolonate salts, due to their strong nucleophilicity and photochemical activity, can promote the coupling reaction between alcohols and carboxylic acid anhydrides or chlorides to give products under thermal or blue light photochemical conditions. Kinetic studies and density functional theory calculations suggest interesting mechanistic insights for reactions promoted by this acyl-transfer catalytic system.
Enol Ester Intermediate Induced Metal-Free Oxidative Coupling of Carboxylic Acids and Arylboronic Acids
Xu, Xianjun,Feng, Huangdi,Li, Huiqiong,Huang, Liliang
, p. 3921 - 3928 (2019/06/24)
A facile, efficient and environmentally friendly methodology for the preparation of phenolic esters is realized via metal-free coupling of carboxylic acids and arylboronic acids. This sequential one pot reaction, employing methyl propiolate as an activating reagent, proceeds through the formation of enol ester intermediate, followed by a nucleophilic attack on the C-O bond under the oxidation of hydrogen peroxide. These studies display that enol esters, despite previously being overlooked as synthetic intermediates, would be the valuable building blocks for developing carbon–carbon and carbon–heteroatom bond-forming reactions.
Ph3P-I2 mediated aryl esterification with a mechanistic insight
Phakhodee, Wong,Duangkamol, Chuthamat,Pattarawarapan, Mookda
supporting information, p. 2087 - 2089 (2016/04/26)
In order to better understand the reaction mechanism and to obtain optimal conditions, the Ph3P-I2/Et3N mediated aryl esterification reaction was thoroughly investigated. Using a specific reagent addition sequence, the reaction proceeds remarkably well especially with acidic substrates. 31P NMR studies revealed that the formation of an aryloxyphosphonium salt is crucial in governing the reaction path toward the formation of phenolic esters.
Copper pincer complexes as advantageous catalysts for the heteroannulation of ortho-halophenols and alkynes
Moure, Maria Jesus,Sanmartin, Raul,Dominguez, Esther
, p. 2070 - 2080 (2014/07/07)
A new, non-symmetrical copper(II) pincer complex catalyzes much more efficiently the formation of benzofuran by the reaction between ortho-iodophenols and alkynes. The lowest catalyst loadings are realized for this reaction, and bromo- and chlorophenols are heteroannulated for the first time. Strong evidence for hydrophenoxylation and intramolecular halogen atom-transfer steps catalyzed by this remarkably active, recyclable homogeneous catalyst is provided.
Synthesis and evaluation of novel benzophenone-thiazole derivatives as potent VEGF-A inhibitors
Prashanth,Thirusangu, Prabhu,Vijay Avin,Lakshmi Ranganatha,Prabhakar,Khanum, Shaukath Ara
, p. 274 - 283 (2015/02/19)
A series of 2-(4-benzoyl-phenoxy)-N-(4-phenyl-thiazol-2-yl)-Acetamides (10a-n) were synthesized by multistep reaction sequence and all the compounds were well characterized for structural elucidation. The in vitro cytotoxicity of compounds 10a-n was evaluated against EAC and DLA cell lines using trypan blue dye exclusion method. Further MTT assay and LDH release assay, followed by in vivo studies on murine model were also evaluated. The compound 10h with a methyl and fluoro groups at benzophenone moiety and methoxy group at phenyl ring was in a leading position to exhibit the promising antiproliferative effect through translational VEGF-A inhibition.
17O NMR study of ortho and alkyl substituent effects in substituted phenyl and alkyl esters of benzoic acids
Nummert, Vilve,Maeemets, Vahur,Piirsalu, Mare,Vahur, Signe,Koppel, Ilmar A.
experimental part, p. 1737 - 1763 (2012/04/17)
17O NMR spectra for 44 ortho-, meta- and para-substituted phenyl and alkyl benzoates (C6H5CO2C 6H4-X, C6H5CO2R) at natural abundance in acetonitrile were re
