770-40-1Relevant articles and documents
Reductive C?N Coupling of Nitroarenes: Heterogenization of MoO3 Catalyst by Confinement in Silica
Yang, Fu,Dong, Xuexue,Shen, Yang,Liu, Mengting,Zhou, Hu,Wang, Xuyu,Li, Lulu,Yuan, Aihua,Song, Heng
, p. 3413 - 3421 (2021/07/31)
The construction of C?N bonds with nitroaromatics and boronic acids using highly efficient and recyclable catalysts remains a challenge. In this study, nanoporous MoO3 confined in silica serves as an efficient heterogeneous catalyst for C?N cross-coupling of nitroaromatics with aryl or alkyl boronic acids to deliver N-arylamines and with desirable multiple reusability. Experimental results suggest that silica not only heterogenizes the Mo species in the confined mesoporous microenvironment but also significantly reduces the reaction induction period and regulates the chemical efficiency of the targeted product. The well-shaped MoO3@m?SiO2 catalyst exhibits improved catalytic performance both in yield and turnover number, in contrast with homogeneous Mo catalysts, commercial Pd/C, or MoO3 nanoparticles. This approach offers a new avenue for the heterogeneous catalytic synthesis of valuable bioactive molecules.
ACETAMIDO DERIVATIVES AS DNA POLYMERASE THETA INHIBITORS
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Paragraph 0176, (2020/08/22)
Disclosed herein are certain acetamido derivatives that are DNA Polymerase Theta (Polθ) inhibitors of Formula (I). Also, disclosed are pharmaceutical compositions comprising such compounds and methods of treating diseases treatable by inhibition of Polθ such as cancer, including homologous recombination (HR) deficient cancers.
Bifunctional Pincer Catalysts for Chemoselective Transfer Hydrogenation and Related Reactions
Cohen, Shirel,Bilyachenko, Alexey N.,Gelman, Dmitri
, p. 3203 - 3209 (2019/02/09)
A comparative study on the chemoselective transfer hydrogenation of nitroarenes to anilines and related processes using FA as the hydrogen source is described; these processes are catalyzed by a series of pincer catalysts equipped with different functional groups in the secondary coordination sphere. Some new (4 and 5) as well as previously reported (1–3) catalysts belonging to the family of bifunctional PC(sp3)P pincer complexes were employed in this study The reported compounds exhibited remarkably different catalytic activity behavior, depending on the nature of the functional groups. Transfer hydrogenation of nitrobenzene with FA as a hydrogen source was probed using iridium complexes 3 or 4 as a catalyst. Under the same conditions, the analogous palladium complex was found to be useful for the selective amidation of aniline with light carboxylic acids.
Hofmann N-alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO2 as a catalyst through Box–Behnken experimental design
Ghanimati, Mahdi,Abdoli Senejani, Masumeh,Isfahani, Tahereh Momeni,Bodaghifard, Mohammad Ali
, (2018/11/06)
An efficient method for the N-alkylation of poorly nucleophilic amines using ferric perchlorate immobilized on SiO2 as a catalyst is described. Fe(ClO4)3 was prepared from mixing iron(III) hydroxide and perchloric acid and adsorbed on silica gel. The catalyst was characterized using various techniques. The supported ferric perchlorate (Fe(ClO4)3/SiO2) revealed high efficiency and selectivity for N-alkylation of aromatic amines with alcohols to provide alkylated amines. Various secondary amines were synthesized from primary amines and alcohols in good to excellent yields, with water as the only by-product. The optimization of the reaction conditions was investigated using the response surface method, and involving the Box–Behnken design matrix. The conditions for optimal reaction yield and time were: amount of catalyst?=?0.34?mmol, temperature?=?60°C and molar ratio of amine to alcohol?=?1.2. The catalyst was recovered and reused for five cycles without a considerable decrease in catalytic activity. The stability of the recycled catalyst was investigated. The proposed method has numerous advantages including procedure simplicity, short reaction times, low cost, good to excellent yields, reusability of the catalyst and mild and environmentally benign conditions.
Nickel(II) complex covalently anchored on core shell structured SiO2@Fe3O4 nanoparticles: A robust and magnetically retrievable catalyst for direct one-pot reductive amination of ketones
Sharma, Rakesh Kumar,Dutta, Sriparna,Sharma, Shivani
, p. 2089 - 2101 (2016/03/19)
A robust and efficient core shell structured magnetically retrievable nickel nanocatalytic system was fabricated via the covalent immobilization of 2-acetyl furan on the surface of an amine functionalized silica coated magnetic nanosupport followed by its metallation with nickel acetate. The newly synthesized magnetic silica based organic-inorganic hybrid nanocatalyst (Ni-ACF@Am-SiO2@Fe3O4) was systematically affirmed using several physico-chemical characterization tools such as FT-IR, XRD, VSM, SEM, TEM, EDS, ED-XRF and AAS. Thereafter, the catalytic performance of this Ni-ACF@Am-SiO2@Fe3O4 nanocatalyst was investigated in the one-pot reductive amination of ketones using NaBH4 as the reductant under neat conditions. The developed core shell magnetic silica based nickel nanocatalyst successfully afforded a structurally diverse range of secondary amines with high turnover frequency (TOF) and excellent conversion percentage. Additionally, it was found that this catalyst could not only be retrieved from the reaction vessel within a fraction of seconds using an external magnet but also be recycled for multiple runs without any discernible loss in its activity that rendered this protocol superior to all the previously established methodologies for the one-pot synthesis of substituted amines. Besides, some of the other fascinating features of this methodology that made it a potential candidate for addressing various economic and environmental concerns were ambient reaction conditions, broad substrate scope, simple workup procedure, shorter reaction time and cost effectiveness.
Alkylation of Amines with Alcohols and Amines by a Single Catalyst under Mild Conditions
Zou, Qingzhu,Wang, Chao,Smith, Jen,Xue, Dong,Xiao, Jianliang
supporting information, p. 9656 - 9661 (2015/06/30)
An efficient catalytic system for the alkylation of amines with either alcohols or amines under mild conditions has been developed, using cyclometallated iridium complexes as catalysts. The method has broad substrate scope, allowing for the synthesis of a diverse range of secondary and tertiary amines with good to excellent yields. By controlling the ratio of substrates, both mono- and bis-alkylated amines can be obtained with high selectivity. In particular, methanol can be used as the alkylating reagent, affording N-methylated products selectively. A strong solvent effect is observed for the reaction.
Chemoselective hydrogenation of functionalized nitroarenes and imines by using carbon nanofiber-supported iridium nanoparticles
Motoyama, Yukihiro,Taguchi, Masahiro,Desmira, Nelfa,Yoon, Seong-Ho,Mochida, Isao,Nagashima, Hideo
, p. 71 - 74 (2014/01/06)
The reaction of three types of carbon nanofibers (CNFs; platelet: CNF-P, tubular: CNF-T, herringbone: CNF-H) with Ir4(CO)12 in mesitylene at 165 °C provided the corresponding CNF-supported iridium nanoparticles, Ir/CNFs (Ir content=2.3-2.6 wt. %). Transmission electron microscopy (TEM) studies of these Ir/CNF samples revealed that size-controlled Ir nanoparticles (average particle size of 1.1-1.5 nm) existed on the CNFs. Among the three Ir/CNF samples, Ir/CNF-T showed an excellent catalytic activity and chemoselectivity towards hydrogenation of functionalized nitroarenes and imines; the corresponding aniline derivatives were obtained with high turnover numbers at ambient temperature under 10 atm of H2, and the catalyst is reusable. Ir/CNF-T was also effective for the reductive N-alkylation of anilines with carbonyl compounds.
Synthesis, reactivities, and catalytic properties of iodo-bridged polymeric iridium complexes with flexible carbon chain-bridged bis(tetramethylcyclopentadienyl) ligands
Tan, Xing,Li, Bin,Xu, Shansheng,Song, Haibin,Wang, Baiquan
, p. 3253 - 3261 (2013/07/19)
Dinuclear iridium complexes [(C5Me4)(CH 2)n(C5Me4)][Ir(COD)]2 (2a: n = 2; 2b: n = 3; 2c: n = 4) are obtained from the reactions of the corresponding dilithium salts Li2/sub
Tertiary alcohols by tandem β-carbolithiation and N→C aryl migration in enol carbamates
Fournier, Anne M.,Clayden, Jonathan
supporting information; experimental part, p. 142 - 145 (2012/02/14)
Enol carbamates (O-vinylcarbamates) derived from aromatic or α,β-unsaturated compounds and bearing an N-aryl substituent undergo carbolithiation by nucleophilic attack at the (nominally nucleophilic) β position of the enol double bond. The resulting carbamate-stabilized allylic, propargylic, or benzylic organolithium rearranges with N→C migration of the N-aryl substituent, creating a quaternary carbon α to O. The products may be readily hydrolyzed to yield multiply branched tertiary alcohols in a one-pot tandem reaction, effectively a polarity-reversed nucleophilic β-alkylation-electrophilic α-arylation of an enol equivalent.
Selective copper-promoted cross-coupling of aromatic amines with alkyl boronic acids
Larrosa, Marta,Guerrero, César,Rodríguez, Ramón,Cruces, Jacobo
supporting information; experimental part, p. 2101 - 2105 (2010/10/03)
A simple copper-promoted N-monoalkylation of anilines that utilizes alkyl boronic acids as the alkylating partner is presented. The reaction is carried out in refluxing dioxane, and it allows a number of structurally and electronically diverse anilines to be functionalized in a single step. A broad study was carried out to demonstrate the utility of this new methodology for the preparation of phenethylanilines.
