2521-92-8Relevant articles and documents
Ethyl cellulose derived porous iron@N-doped carbon material for N–H carbene insertion reaction
Lin, Yamei,Wang, Fei,Lu, Guo-Ping,Zhang, Xing
, (2021/09/08)
A newly developed, facile and sustainable strategy, in which zinc salt, melamine and ethyl cellulose are applied as pore-forming agent, nitrogen and carbon source respectively, has been disclosed for the synthesis of Fe/N-codoped carbon materials. This material exhibits excellent catalytic efficiency towards N–H carbene insertion reaction for the synthesis of unnatural amino acid derivatives. Fe/FeOx nanoparticles tranfer electrons to N-doped carbon owing to the Mott-Schottky Effect, which is beneficial to the formation of iron carbene intermediate. N-doping can offer more Lewis base sites, which promotes the proton transfer process. Fe/FeOx nanoparticles are coated with graphitic carbon, thereby avoiding the loss and deactivation of iron sites in this material. Therefore, this material can be reused at least four times without significant loss in activity.
Preparation method of N-aryl glycine ester derivative
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Paragraph 0047-0052, (2020/07/12)
The invention relates to a preparation method of an N-aryl glycine ester derivative. The invention aims to solve the problems of complex steps and environmental pollution in the existing method for synthesizing the N-aryl glycine ester derivative. The preparation method comprises the following steps: dissolving an aryl primary amine compound, ethyl diazoacetate, a reaction aid and a photocatalystin an organic solvent at room temperature, uniformly mixing, reacting under a blue LEDs lamp, carrying out reduced pressure distillation to remove the solvent, and separating and purifying to obtain the product. The problems of high energy consumption, high cost and environmental pollution caused by high temperature, biocatalyst or metal organic framework required by the synthesis of the existingN-aryl glycine ester derivative are solved. A route for synthesizing the N-arylglycine ester derivative, which is green, efficient, mild in condition, simple in method, convenient to operate and highin yield, is found, and the method is applied to the field of organic synthesis.
Access to α-Amino Acid Esters through Palladium-Catalyzed Oxidative Amination of Vinyl Ethers with Hydrogen Peroxide as the Oxidant and Oxygen Source
Ouyang, Lu,Li, Jianxiao,Zheng, Jia,Huang, Jiuzhong,Qi, Chaorong,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 15926 - 15930 (2017/11/23)
A novel and convenient palladium catalytic system for the synthesis of α-amino acid esters from simple starting materials is reported. Hydrogen peroxide not only acts as the green oxidant, but also as the oxygen source. This strategy for the conversion of amines and vinyl ethers into highly functionalized and structurally diverse α-amino acid esters is characterized by the simplicity of the experimental procedure, mild reaction conditions, high atom economy, scalability, and practicability.
Dual role of Cu2O nanocubes as templates and networking catalysts for hollow and microporous Fe-porphyrin networks
Kang, Daye,Ko, Ju Hong,Choi, Jaewon,Cho, Kyoungil,Lee, Sang Moon,Kim, Hae Jin,Ko, Yoon-Joo,Park, Kang Hyun,Son, Seung Uk
supporting information, p. 2598 - 2601 (2017/03/09)
Cu2O nanocubes were used for the synthesis of hollow and microporous Fe porphyrin networks (H-MFePN). In this synthesis, Cu2O nanocubes performed not only as networking catalysts but also as shape controlling templates. MFePN were formed on the surface of the Cu2O nanocubes through azide-alkyne cycloaddition of tetrakis(4-ethynylphenyl) Fe-porphyrin with 1,4-diazidobenzene. H-MFePN showed excellent catalytic activities in carbene insertion into N-H bonds, maintaining their activities during five recycle tests.
Stable radical cation salt initiated N-H insertion and related proton-transfer-delay three-component reaction
Huo, Congde,Xie, Haisheng,Yang, Caixia,Dong, Jie,Wang, Yajun
, p. 2179 - 2182 (2016/05/02)
The N-H insertion reaction forms the single addition product exclusively, and does not require slow addition of the diazo component. More importantly, we present the reaction of anilines with both diazoacetates and azodicarboxylates in the presence of catalytic amounts of triarylaminium salt giving the corresponding complex unsymmetrical aminals in high yields. This is the first example of stable radical cation salt promoted proton-transfer-delay three-component reaction.
A series of robust metal-porphyrinic frameworks based on rare earth clusters and their application in N-H carbene insertion
Xu, Lei,Zhai, Meng-Ke,Wang, Fei,Sun, Lin,Du, Hong-Bin
, p. 17108 - 17112 (2016/11/13)
We herein report a series of microporous metal-porphyrinic frameworks (MPFs), denoted as NUPF-2M, based on rare earth (RE) clusters. NUPF-2M represent the first examples of RE cluster-based MPFs, possessing a rarely seen shp-a topology and exhibiting high thermal and thermal stabilities. After a post-metallization process with FeCl3, NUPF-2M is catalytically active as an efficient heterogeneous catalyst for intermolecular N-H carbene insertion.
1-Methylimidazolium tetrafluoroborate [Hmim][BF4]: An efficient acidic ionic liquid catalyst for insertion of α-diazo compounds into the N-H bonds of amines
Akbari, Jafar,Ebrahimi, Ali,Heydari, Akbar
, p. 5417 - 5419 (2014/12/11)
The reusable acidic ionic liquid, 1-methylimidazolium tetrafluoroborate [Hmim][BF4], was found to be an effective catalyst for the insertion of α-diazoacetate into the N-H bonds of amines. The corresponding products were obtained in good yields and short reaction times via a simple procedure. The catalyst could be recycled and reused without any noticeable decrease in its activity.
Direct amide formation from N-arylglycine ethyl esters and carboxylic acids catalysed by phenylboronic acid
Huang, Wenhua,Sha, Wen-Bin
, p. 460 - 463 (2013/09/12)
The phenylboronic acid-catalysed reaction of an N-arylglycine ethyl ester with various carboxylic acids, including N-acyl-N-phenylglycines, directly affords an amide or a dipeptide in 13-73% yields.
Transition metal complexes of novel ethyl pyruvate hydrazones as potential antitumor agents: Synthesis and physicochemical properties, DNA interactions and antiproliferative activity
Pathan, Aishakhanam H.,Gudasi, Kalagouda B.
, p. 1504 - 1516 (2013/05/08)
A new series of ethyl pyruvate hydrazones and their later first row transition metal(II) complexes have been synthesized and characterized by means of elemental analyses, vibrational, electronic, 1H and 13C NMR, electron paramagnetic resonance, and mass spectroscopic techniques along with thermal and magnetic studies. All complexes were found to be monomeric in nature and have octahedral geometry. The prepared compounds were evaluated for antiproliferative activity against the two human cancer cell lines (HeLa and HepG2). The Cu(II) complexes were found to have potential activity against the cell lines used than the ligand and other complexes. In addition, the DNA-binding/cleaving capacity of the compounds were analyzed by absorption spectroscopy, viscosity measurement, thermal denaturation studies and gel electrophoresis methods.
Iridium porphyrin catalyzed N-H insertion reactions: Scope and mechanism
Anding, Bernie J.,Woo, L. Keith
, p. 2599 - 2607 (2013/06/26)
Ir(TTP)CH3 catalyzed N-H insertion reactions between ethyl diazoacetate (EDA) or methyl phenyldiazoacetate (MPDA) and a variety of aryl, aliphatic, primary, and secondary amines to generate substituted glycine esters with modest to high yields. Aniline substrates generally gave yields above 80%, with up to 105 catalyst turnovers, and without slow addition of the diazo reagent. Good yields were also achieved with aliphatic amines, though higher catalyst loadings and slow addition of the amine were necessary in some cases. Primary amines reacted with EDA to generate both single- and double-insertion products, either of which could be produced selectively in high yield with the proper choice of stoichiometric ratios and reaction temperature. Notably, mixed trisubstituted amines, RN(CH2CO2Et) (CHPhCO2Me), were generated from the insertion of 1 equiv of EDA and 1 equiv of MPDA into primary amines. The N-H insertion mechanism was examined using substrate competition studies, trapping experiments, and multiple spectroscopic techniques. Substrate competition studies using pairs of amines with EDA or MPDA revealed Hammett correlations with respective slopes of ρ = 0.15 and ρ+ = -0.56 as well as kinetic isotope ratios of k H/kD = 1.0 ± 0.2 and 2.7 ± 0.2. Competitive amine binding to the iridium center was demonstrated by kinetics and equilibrium binding studies. Equilibrium binding constants ranged from 102 to 105. Monitoring the reaction by absorption spectroscopy revealed a transient metalloporphyrin complex. The lifetime of this species was dependent on the nature of the amine substrate, which suggests that the catalytic cycle proceeds through a metal-ylide intermediate.
