- Facile one-pot multicomponent synthesis of highly functionalized tetrahydropyridines using thiamine hydrochloride as an organocatalyst
-
Thiamine hydrochloride (VitB1) has been found to be an efficient catalyst for the multicomponent synthesis of highly functionalized tetrahydropyridines from the reaction of β-ketoester, aromatic aldehydes and anilines. VitB1 is easily available, cheap, and eco benign.
- Singh, Sandeep,Gupta, Annah,Kapoor, Kamal K.
-
supporting information
p. 1056 - 1063
(2020/03/04)
-
- 5-Hydroxyindole-based EZH2 inhibitors assembled via TCCA-catalyzed condensation and Nenitzescu reactions
-
5-Hydroxyindole derivatives have various demonstrated biological activities. Herein, we used 5-hydroxyindole as a synthetic starting point for structural alterations in a combinatorial process to synthesize 22 different compounds with EZH2 inhibitor pharmacophores. A series of 5-hydroxyindole-derived compounds were screened inhibitory activities against K562 cells. According to molecular modeling and in vitro biological activity assays, the preliminary structure-activity relationship was summarized. Compound L–04 improved both the H3K27Me3 reduction and antiproliferation parameters (IC50 = 52.6 μM). These findings revealed that compound L–04 is worthy of consideration as a lead compound to design more potent EZH2 inhibitors. During the preparation of compounds, we discovered that trichloroisocyanuric acid (TCCA) is a novel catalyst which demonstrates condensation-promoting effects. To gain insight into the reaction, in situ React IR technology was used to confirm the reactivity. Different amines were condensed in high yields with β-diketones or β-ketoesters in the presence of TCCA to afford the corresponding products in a short time (10~20 min), which displayed some advantages and provided an alternative condensation strategy.
- Chen, Guoliang,Du, Fangyu,Sun, Wenjiao,Wang, Lihui,Wu, Chunfu,Yang, Cheng,Zhou, Qifan
-
-
- Multicomponent reaction for the synthesis of highly functionalized piperidine scaffolds catalyzed by TMSI
-
An efficient method for the synthesis of highly functionalized piperidines via one-pot domino reaction of β-ketoesters, aromatic aldehydes, and aromatic amines was reported. This multicomponent coupling was catalyzed by TMSI in methanol at room temperature, giving desired substituted pyridines in moderate to good yields.
- Wu, Lisha,Yan, Shiqiang,Wang, Wensheng,Li, Yinta
-
p. 4311 - 4322
(2020/07/13)
-
- Base-Catalyzed Tandem Cyclization: Diastereoselective Access to the 3,4-Dihydroisoquinolin-2(1 H)-one Core
-
A novel, one-pot reaction for the synthesis of 3,4-dihydroisoquinolin-2(1 H)-one derivatives is developed via a base-mediated three-component reaction of ninhydrin, aniline and acetylenic esters. This diastereoselective reaction takes place in methanol at 70A °C under transition-metal-free conditions, and direct construction of the C-N and C-C bonds is readily achieved via tandem cyclization. These cyclic frameworks are resourceful small molecular keys to many natural products.
- Shirsat, Prashishkumar K.,Khomane, Navnath B.,Meshram, Sneha H.,Sridhar, Balasubramanian,Meshram, Harshadas M.,Kumbhare, Ravindra M.
-
supporting information
p. 1473 - 1481
(2019/03/13)
-
- A simple route towards the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles from primary amines and 1,3-dicarbonyl compounds under metal-free conditions
-
An acetic acid-promoted approach that enables the synthesis of 1,4,5-trisubstituted 1,2,3-triazole derivatives has been achieved. This transformation employs readily available primary amines, 1,3-dicarbonyls and tosyl azide as the starting materials via a
- Guo, Ningxin,Liu, Xiufen,Xu, Hongyan,Zhou, Xi,Zhao, Huaiqing
-
supporting information
p. 6148 - 6152
(2019/07/03)
-
- Lipophilic Indole-Catalyzed Intermolecular Bromoesterification of Olefins in Nonpolar Media
-
An environmentally benign and highly versatile catalytic protocol has been successfully applied in the intermolecular bromoesterification between various olefins and carboxylic acids. The use of a highly lipophilic indole catalyst and 1,3-dibromo-5,5-dime
- Shi, Yao,Wong, Jonathan,Ke, Zhihai,Yeung, Ying-Yeung
-
p. 4017 - 4024
(2019/03/26)
-
- Synthesis of 3 H -Pyrrolo[2,3- c ]quinoline by Sequential i 2 -Promoted Cyclization/Staudinger/Aza-Wittig/Dehydroaromatization Reaction
-
A facile synthetic approach to access of 3 H -pyrrolo[2,3- c ]quinoline derivatives has been achieved by a sequential I 2 -promoted cyclization/Staudinger/aza-Wittig/dehydroaromatization reaction. The targeted products were received in moderate
- Zou, Fakai,Pei, Fei,Wang, Liping,Ren, Zhilin,Cheng, Xiaohong,Sun, Yang,Wu, Jing,He, Ping
-
p. 717 - 720
(2019/03/26)
-
- Quinolones modulate ghrelin receptor signaling: Potential for a novel small molecule scaffold in the treatment of cachexia
-
Cachexia is a metabolic wasting disorder characterized by progressive weight loss, muscle atrophy, fatigue, weakness, and appetite loss. Cachexia is associated with almost all major chronic illnesses including cancer, heart failure, obstructive pulmonary disease, and kidney disease and significantly impedes treatment outcome and therapy tolerance, reducing physical function and increasing mortality. Current cachexia treatments are limited and new pharmacological strategies are needed. Agonists for the growth hormone secretagogue (GHS-R1a), or ghrelin receptor, prospectively regulate the central regulation of appetite and growth hormone secretion, and therefore have tremendous potential as cachexia therapeutics. Non-peptide GHS-R1a agonists are of particular interest, especially given the high gastrointestinal degradation of peptide-based structures, including that of the endogenous ligand, ghrelin, which has a half-life of only 30 min. However, few compounds have been reported in the literature as non-peptide GHS-R1a agonists. In this paper, we investigate the in vitro potential of quinolone compounds to modulate the GHS-R1a in both transfected human cells and mouse hypothalamic cells. These chemically synthesized compounds demonstrate a promising potential as GHS-R1a agonists, shown by an increased intracellular calcium influx. Further studies are now warranted to substantiate and exploit the potential of these novel quinolone-based compounds as orexigenic therapeutics in conditions of cachexia and other metabolic and eating disorders.
- Torres-Fuentes, Cristina,Pastor-Cavada, Elena,Cano, Rafael,Kandil, Dalia,Shanahan, Rachel,Juan, Rocio,Shaban, Hamdy,McGlacken, Gerard P.,Schellekens, Harri?t
-
-
- TBAI or KI-Promoted Oxidative Coupling of Enamines and N-Tosylhydrazine: An Unconventional Method toward 1,5- and 1,4,5-Substituted 1,2,3-Triazoles
-
A novel method for the synthesis of 1,5- and 1,4,5-substituted 1,2,3-triazoles has been reported. This approach is promoted by iodine-TBHP oxidation system using enamines and N-tosylhydrazine as materials, which avoid the dependence of traditional methods on azides and transition metals. Through this approach, various 1,5- and 1,4,5-substituted 1,2,3-triazoles were delivered in moderate to high yields. The mechanistic study indicated that an amino exchange would be involved in the reaction process. Moreover, the product methyl 1-(2-methoxyphenyl)-4-methyl-1H-1,2,3-triazole-5-carboxylate is a useful precursor to anti-influenza A agent, and further application research was conducted. (Figure presented.).
- Huang, Wei,Zhu, Chuanle,Li, Minke,Yu, Yue,Wu, Wanqing,Tu, Zhengchao,Jiang, Huanfeng
-
supporting information
p. 3117 - 3123
(2018/08/01)
-
- PHARMACEUTICAL COMPOSITION AND APPLICATION REPLACING QUINOLONE DERIVATIVE, PHARMACEUTICAL ACCEPTABLE SALT, OR STEREOISOMER
-
Provided are a substituted quinolone derivative as shown by formula (I), or a pharmaceutically acceptable salt and a prodrug molecule thereof, and a pharmaceutical composition thereof, as well as the use of same in preparing drugs for the prevention and treatment of a tumor. The quinolone derivative, salt, prodrug molecule, and pharmaceutical composition thereof can be used as a protein kinase inhibitor, which is effective in inhibiting the activity of AXL protein kinase, and is capable of inhibiting the proliferation, migration and invasion of various tumor cells; and can be used in the preparation of anti-tumor drugs, especially drugs for treating hyperproliferative diseases such as a tumor in human beings and other mammals.
- -
-
Paragraph 0224; 0226
(2018/07/06)
-
- Passerini/tsuji–trost strategy towards pyrrole derivatives
-
The Passerini reaction of α,β-unsaturated aldehydes affords suitable substrates for a Tsuji–Trost reaction with NH-enamines. The latter behave as a 1,3-bisnucleophile, which leads to the formation of pyrrole derivatives with five points of diversity through a Tsuji–Trost/Michael addition/aromatization cascade.
- Narboni, Noisette,El Kaim, Laurent
-
supporting information
p. 4242 - 4246
(2018/08/28)
-
- Graphene oxide: A carbocatalyst for the one-pot multicomponent synthesis of highly functionalized tetrahydropyridines
-
A simple, straightforward and efficient methodology is described for the synthesis of polysubstituted tetrahydropyridine via one-pot multicomponent reaction of β-ketoester, aldehyde and aniline in presence of catalytic amount of graphene oxide in acetonitrile. Graphene oxide is a versatile carbocatalyst and this is the first report on its application in a five component reaction. Good yield, usage of readily available starting material, operational simplicity, easy work-up and eco-friendly re-usable catalyst are the key features of this protocol.
- Gupta, Annah,Kaur, Ramneet,Singh, Deepika,Kapoor, Kamal K.
-
p. 2583 - 2587
(2017/06/13)
-
- MgFe2O4/cellulose/SO3H nanocomposite: a new biopolymer-based nanocatalyst for one-pot multicomponent syntheses of polysubstituted tetrahydropyridines and dihydropyrimidinones
-
A new biopolymer cellulose-based magnetic heterogeneous catalyst, MgFe2O4/cellulose/SO3H nanocomposite, was prepared. Fourier-transform infrared spectra, X-ray diffraction, energy-dispersive X-ray, field-emission scanning electron microscopy, thermal analysis (TG, DTG and DSC), dynamic light scattering and vibrating sample magnetometer measurements have been used to characterize the catalyst. Then, it was applied efficiently as an inexpensive and green catalyst in two multicomponent syntheses of polysubstituted tetrahydropyridines and dihydropyrimidinones under solvent-free conditions. The nanocatalyst can be recovered and reused several times without significant loss of catalytic activity.
- Maleki, Ali,Jafari, Abbas Ali,Yousefi, Somayeh
-
p. 1801 - 1813
(2017/06/27)
-
- Tandem Copper-Catalyzed Propargylation/Alkyne Azacyclization/Isomerization Reaction under Microwave Irradiation: Synthesis of Fully Substituted Pyrroles
-
A copper-catalyzed and microwave-assisted synthesis of fully substituted pyrroles has been developed. A series of pentasubstituted pyrroles, especially α-arylpyrroles, could be obtained in moderate to good yields (up to 93%) through a tandem propargylation/alkyne azacyclization/isomerization sequence from readily available β-enamino compounds and propargyl acetates.
- Zhang, Xiao-Yan,Yang, Zhi-Wei,Chen, Zhongzhu,Wang, Jun,Yang, Dong-Lin,Shen, Ze,Hu, Li-Li,Xie, Jian-Wu,Zhang, Jin,Cui, Hai-Lei
-
p. 1778 - 1785
(2016/03/15)
-
- Synthesis of β-enamino acid and heteroaryl acetic acid derivatives by Pd-catalyzed carbonylation of α-chloroimines and 2-chloromethyl aza-heterocycles
-
β-Enamino esters or amides can be synthesized in a single step by a carbonylative coupling of α-chloroimines with alcohols or amines under Pd-catalysis. The methodology has been also applied to the preparation of heteroaryl acetic acid derivatives starting from chloromethyl heteroaromatic rings containing a C-N double bond. The in situ generation of a β-imino acylpalladium species has been proposed as a key step for the process.
- Perrone, Serena,Capua, Martina,Cannazza, Giuseppe,Salomone, Antonio,Troisi, Luigino
-
supporting information
p. 1421 - 1424
(2016/03/12)
-
- Bimetallic Ag-Cu alloy nanoparticles as a highly active catalyst for the enamination of 1,3-dicarbonyl compounds
-
Bimetallic nanoparticles, particularly those based on copper, have recently attracted a great deal of attention for the development of low cost and highly active catalysts due to the synergistic interaction between individual metal components. In this work, bimetallic Ag-Cu alloy nanoparticles were explored as a highly active and reusable catalyst for the enamination of 1,3-dicarbonyls using diverse amines. The nanocatalysts were intensively characterized by ultraviolet-visible (UV-Vis) spectroscopy, X-ray diffraction (XRD), high-resolution transmission electron microscopy-energy-dispersive spectroscopy (HRTEM-EDS) and valence band and core level X-ray photoelectron spectroscopy (XPS) to study the effect of the bimetallic structure and composition. In comparison to monometallic Ag and Cu nanoparticles, the alloyed Ag-Cu nanoparticles showed a high catalytic performance and the resultant catalytic activity was dependant on the Ag to Cu ratio. This enhanced catalytic activity should be related to the electronic interaction between Ag and Cu nanoparticles formed due to the intimate contact between them. Our study may serve as a foundation for designing efficient alloyed nanocatalysts for fine chemical synthesis via enamination reactions.
- Rout, Lipeeka,Kumar, Aniket,Dhaka, Rajendra S.,Dash, Priyabrat
-
p. 49923 - 49940
(2016/06/15)
-
- Effect of solvent ratio and counter ions on the morphology of copper nanoparticles and their catalytic application in β-enaminone synthesis
-
This work reports the synthesis of shape selective copper nanoparticles (NPs) using a microwave irradiation method, using diverse ratios of an ethylene glycol (EG)/water system. The solvent ratio of EG/water plays a pivotal role in the selective formation of CuO NPs. The alteration of the counter ion of the copper precursor leading to the selective synthesis of copper (CuO, Cu2O, Cu(OH)2) NPs has been observed. The synthesized copper NPs are well characterized using FEG-SEM, TEM, XRD, XPS, NH3-TPD and BET surface area. The prepared CuO NPs show high activity towards the synthesis of β-enaminones and β-enamino esters from 1,3 diketones and amines.
- Gajengi, Aravind L.,Sasaki, Takehiko,Bhanage, Bhalchandra M.
-
p. 101800 - 101807
(2016/11/09)
-
- 4-Oxo-1,4-dihydroquinoline-3-carboxamide Derivatives as New Axl Kinase Inhibitors
-
Axl is a new potential target for anticancer drug discovery. A series of 4-oxo-1,4-dihydroquinoline-3-carboxamides were designed and synthesized as highly potent Axl kinase inhibitors. One of the most promising compounds, 9im, tightly bound with Axl prote
- Tan, Li,Zhang, Zhang,Gao, Donglin,Luo, Jinfeng,Tu, Zheng-Chao,Li, Zhengqiu,Peng, Lijie,Ren, Xiaomei,Ding, Ke
-
supporting information
p. 6807 - 6825
(2016/08/05)
-
- Calix[n]arenes: Active organocatalysts for the synthesis of densely functionalized piperidines by one-pot multicomponent procedure
-
An efficient, suitable and high yielding method has been developed for the synthesis of different densely functionalized piperidine derivatives via pseudo-five component, one-pot domino reaction through a combination of β-ketoesters, aromatic aldehydes, and various amines using p-sulfonic acid calix[n]arenes as catalysts. The reaction was carried out in refluxing methanol, affording very good yields of the expected piperidine. Atomic economy, environmentally benign procedure, reuse of catalysts, and short reaction time are some of the important features of this protocol.
- Palermo,Sathicq,Liberto,Fernandes,Langer,Jios,Romanelli
-
supporting information
p. 2049 - 2054
(2016/04/26)
-
- Three naphthalenedisulfonate polymers with imidazole-containing ligands: Synthesis, structure and heterogeneously catalytic performance in reactions of enamination of β-dicarbonyl compounds
-
Three new naphthalenedisulfonate polymers, [Cd(2,6-nds)(bib)]n (1), [Cd(1,5-nds)(bib)]n (2), and [Cu(2,6-nds)0.5(tpim)]n (3), have been successfully synthesized by hydrothermal reactions of corresponding metal salts with naphthalenedisulfonate (nds) and imidazole-containing ligands 1,4-bis(imidazol-1-ylmethyl)benzene (bib) and 2,4,5-tri(4-pyridyl)-imidazole (tpim). The structures of these polymers were determined by single crystal X-ray diffraction analysis. Polymers 1 and 2 crystallize in the same space group and have similar cell parameters, and thus show same three-dimensional (3D) framework architecture. Complex 3 has the same 2D layer structure. The photoluminescent properties of the complexes 1 and 2 were investigated. Catalytic tests indicate that complex 3 has chemo-and regio-selective catalytic activity towards enamination of β-ketoesters.
- Wang, Li,Liu, Jing,Guo, Hui,Deng, Dongsheng,Yao, Tian,Wang, Xingwei,Wang, Xinyi,Wu, Hongli
-
supporting information
p. 253 - 260
(2015/04/14)
-
- Design of a graphene oxide-SnO2 nanocomposite with superior catalytic efficiency for the synthesis of β-enaminones and β-enaminoesters
-
A graphene oxide (GO)-SnO2-based nanocomposite was synthesized by decorating the graphene oxide surface with SnO2 nanoparticles via a solvothermal process. The nanocomposite was characterized using Fourier transform infrared spectra (FTIR), FT-Raman spectroscopy, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Field-emission Scanning electron microscopy (FE-SEM), Energy dispersive X-ray spectroscopy (EDS), Transmission electron microscopy (TEM) and N2 adsorption/desorption study. The FE-SEM and TEM images demonstrate the uniform distribution of the SnO2 nanoparticles on the GO surface and high-resolution transmission electron microscopy (HRTEM) confirms an average particle size of 8-12 nm. The GO-SnO2 nanocomposite has been found to be an extremely efficient catalyst for the synthesis of β-enaminones and β-enaminoesters in methanol solvent and also, in solventless conditions. The GO-SnO2 nanocomposites exhibited synergistically more superior catalytic efficiency compared to pure graphene oxide and SnO2 nanoparticles. The reaction conditions were optimized by changing different parameters such as catalyst, solvent, catalyst loading, and temperature. It has been found that the catalyst gave higher activity under solventless conditions than methanol. The GO-SnO2 composite was recycled for up to four cycles with minimal loss in activity.
- Kumar, Aniket,Rout, Lipeeka,Dhaka, Rajendra S.,Samal, Saroj L.,Dash, Priyabrat
-
p. 39193 - 39204
(2015/05/20)
-
- Indole-Catalyzed Bromolactonization in Lipophilic Solvent: A Solid-Liquid Phase Transfer Approach
-
We have developed a novel indole-catalyzed bromolactonization of olefinic acids. The reaction could be conducted in lipophilic solvent through a solid-liquid phase transfer mechanism. This catalytic protocol has been applied to the synthesis of base-sensitive bromolactones. (Chemical Equation Presented).
- Chen, Tao,Foo, Thomas Jian Yao,Yeung, Ying-Yeung
-
p. 4751 - 4755
(2015/08/18)
-
- Fabrication of Ag/γ-Fe2O3@TiO2 hollow magnetic core-shell nanospheres as highly efficient catalysts for the synthesis of β-enaminones
-
Herein, we describe a method to prepare hollow magnetic mesoporous sphere catalysts (Ag/γ-Fe2O3@meso-TiO2). The core-shell strategy efficiently prevents the aggregation of Ag NPs in the high temperature calcination process and the leaching of Ag NPs for the catalytic reaction in the liquid phase. The catalyst is characterized by TEM, XRD and ICP-AES. Moreover, the catalyst exhibited improved activity for the synthesis of β-enaminones, and it could be easily recovered by an external magnet from the reaction mixture and recycled five times without any significant loss in activity.
- Huo, Hongfei,Li, Xinzhe,Zhou, Xingchun,Jiao, Lixin,Zhao, Shiling,Zhang, Le,Li, Wenzhu,Li, Shuwen,Li, Rong
-
p. 73612 - 73618
(2015/09/15)
-
- Solvent-free synthesis of β-enamino ketones and esters catalysed by recyclable iron(III) triflate
-
A novel application of highly stable Fe(OTf)3 as an efficient catalyst for the synthesis of a variety of β-enamino ketones and esters under solvent-free conditions is described. Notably, this protocol of a "green synthesis", which produced β-enamino ketones and esters by the reaction of a variety of β-dicarbonyl compounds and primary amines, exhibits attractive properties including high yields, short reaction periods, lower loading of catalyst and chemo- and regio-selectivity. In addition, the catalyst was easily recovered from the reaction system and readily reused with minimal loss of activity.
- Feng, Cheng-Liang,Chu, Ning-Ning,Zhang, Shu-Guang,Cai, Jin,Chen, Jun-Qing,Hu, Hua-You,Ji, Min
-
p. 1097 - 1103
(2014/05/20)
-
- Ferric nitrate nonahydrate as a mild and efficient catalyst for the synthesis of ss-enaminones
-
Ferric nitrate nonahydrate (Fe(NO3)3 -9H 2O) has been found to be an extremely mild and efficient catalyst for the preparation of ss-enaminones from ss-dicarbonyl compounds and amines (aliphatic amines, aromatic amines and
- Khajuria, Rajni,Ambica,Saini, Yeshwinder,Kapoor, Kamal K.
-
p. 1122 - 1127
(2014/10/15)
-
- K-10 clay as a reusable catalyst for the solvent-free, MW-induced synthesis of enaminones
-
A series of β-amino-a,β-unsaturated ketones and esters were synthesized in good to excellent yields from the reaction of different amines with 1,3-dicarbonyl compounds in solvent-free media using montmorillonite K-10 clay as.
- Marvi, Omid,Giahi, Masoud,Ayub, Pouran Pur,Nikpasand, Mohammad
-
p. 921 - 926
(2014/11/07)
-
- A general and efficient method for synthesis of enaminones and enamino esters catalyzed by NbCl5 under solvent-free conditions
-
A general and simple procedure was developed for the synthesis of β-enaminones and β-enamino esters by reacting 1,3-dicarbonyl compounds with amines in the presence of catalytic amounts of niobium pentachloride. The reaction proceeds smoothly at room temperature under solvent-free conditions and leads to chemo- and regioselective formation of enamine derivatives in high to excellent yields.
- Liu, Yu-Heng,Wang, Ping,Cheng, Gui-Tian
-
p. 191 - 196
(2013/07/27)
-
- Zinc triflate catalysed synthesis of β-enamino ketones(esters) under solvent-free conditions
-
An efficient and mild procedure is described for the synthesis of a series of β-enamino ketones(esters) from 1,3-dicarbonyl compounds and aliphatic and aromatic amines using zinc triflate as the catalyst.
- Feng, Chengliang,Zhang, Shuguang,Cai, Jin,Chen, Junqing,Hu, Huayou,Ji, Min
-
p. 626 - 629
(2013/11/06)
-
- Vanadium(IV) acetylacetonate catalyzed stereoselective synthesis of β-enaminoesters and β-enaminones
-
An efficient and stereoselective procedure has been described for the synthesis of a series of β-enaminoesters and β-enaminones by vanadium(IV) acetylacetonate [VO(acac)2] catalyzed reaction of β-ketoesters and 1,3-diketones with both aliphatic and aromatic amines. X-ray crystallographic studies of some representative compounds corroborate two types of structural geometry formed by inter-molecular as well as intra-molecular hydrogen bonds.
- Laskar, Rajibul A.,Begum, Naznin A.,Hedayetullah Mir, Mohammad,Ali, Shahzad,Khan, Abu T.
-
p. 436 - 440
(2013/02/23)
-
- Oxidative cross-coupling/cyclization to build polysubstituted pyrroles from terminal alkynes and β-enamino esters
-
A novel silver-mediated highly selective synthesis of polysubstituted pyrroles by the C-H/C-H oxidative cross-coupling/cyclization of terminal alkynes with β-enamino esters has been developed. This protocol represents a simple, efficient and selective way to construct polysubstituted pyrroles in good yields from basic chemical materials.
- Ke, Jie,He, Chuan,Liu, Huiying,Li, Mengjun,Lei, Aiwen
-
supporting information
p. 7549 - 7551
(2013/08/23)
-
- Ag/CNT-catalyzed hydroamination of activated alkynes with aromatic amines
-
As a nanoparticle support material, carbon nanotubes (CNTs) provide a certain potential activation of catalysis in heterogeneous catalytic organic reactions. Herein, an efficient Ag/CNT-catalyzed synthesis of enamines via hydroamination of activated alkynes with aromatic amines has been described. This catalyst still retains catalytic activity after being recycled and reused three times. In addition, it represents a green and environmentally friendly process for preparation of enamines. Copyright 2013 John Wiley & Sons, Ltd. Ag/CNTs catalysis has been developed to synthesize enamines via hydroamination of asymmetry alkylnates with aromatic amines. The catalysis can be recycled and reused 3 times, which also remain catalytic activity. In addition, it represents a green and environmentally friendly process for preparation of enamines. Copyright
- Liu, Yi,Wu, Guojie,Cui, Yingde
-
p. 206 - 208
(2013/06/05)
-
- P2W18O62·24H2O as an efficient and recyclable catalyst for the ecofriendly preparation of β-aminocrotonates
-
H6P2W18O62·24H 2O bulk-and silica-supported catalysts were found to be efficient and recyclable catalysts for the synthesis of a series of β-aminocrotonates using toluene as the solvent or under no solvent reaction conditions. Several substituted β-aminocrotonates can be prepared in very good yields and purity by direct reaction of amines and 1,3-dicarbonyl compounds in the presence of a catalytic amount of bulk-and silica-gel-supported H6P 2W18O62·24H2O. The title compounds were prepared in very good yields using both methodologies, and no secondary products were detected. The procedure using no reaction solvent resulted in a clean and useful alternative, which has the advantages of a greener methodology with operative simplicity, the use of a reusable and noncorrosive solid catalyst, soft reaction conditions, low reaction times, and good yields.
- Sanchez, Laura M.,Sathicq, Angel G.,Baronetti, Graciela T.,Thomas, Horacio J.,Romanelli, Gustavo P.
-
p. 137 - 142
(2013/06/05)
-
- Silica supported Fe(HSO4)3 as an efficient, heterogeneous and recyclable catalyst for synthesis of β-enaminones and β-enamino esters
-
A series of β-substituted enaminones were prepared through the one-pot reaction of β-dicarbonyl compounds with various amines in the presence of silica ferric hydrogensulfate under solvent free conditions at room temperature. The reactions proceed smoothl
- Eshghi, Hossein,Seyedi, Seyed Mohammad,Safaei, Elham,Vakili, Mohammad,Farhadipour, Abolghasem,Bayat-Mokhtari, Mohtaram
-
p. 430 - 436
(2012/10/30)
-
- Cross-dehydrogenative coupling between enamino esters and ketones: Synthesis of tetrasubstituted pyrroles
-
Tetrasubstituted pyrroles have been synthesized via the cross-dehydrogenative coupling between enamino esters and acetone. Silver carbonate proved to be an effective oxidant, and no transition metal catalyst is necessary.
- Zhao, Miao,Wang, Fen,Li, Xingwei
-
supporting information; experimental part
p. 1412 - 1415
(2012/05/04)
-
- Cu(OAc)2/TFA-promoted formal [3 + 3] cycloaddition/oxidation of enamines and enones for synthesis of multisubstituted aromatic amines
-
New strategies for the oxidative cycloaddition of enones with enamines are developed. These cycloaddition reactions directly afford substituted aromatic amines, which are important in organic chemistry, in moderate to good yield. Cu(OAc)2/TFA is shown to be essential to achieve high reaction efficiency.
- Li, Liang,Zhao, Mi-Na,Ren, Zhi-Hui,Li, Jian-Li,Guan, Zheng-Hui
-
supporting information; experimental part
p. 3506 - 3509
(2012/08/08)
-
- Exploring the oxidative cyclization of substituted N-aryl enamines: Pd-catalyzed formation of indoles from anilines
-
The direct Pd-catalyzed oxidative coupling of two C-H-bonds within N-aryl-enamines 1 allows the efficient formation of differently substituted indoles 2. In this cross-dehydrogenative coupling, many different functional groups are tolerated and the starting material N-aryl-enamines 1 can be easily prepared in one step from commercially available anilines. In addition, the whole sequence can also be run in a one-pot fashion. Optimization data, mechanistic insight, substrate scope, and applications are reported in this full paper. Copyright
- Neumann, Julia J.,Rakshit, Souvik,Droege, Thomas,Wuertz, Sebastian,Glorius, Frank
-
supporting information; experimental part
p. 7298 - 7303
(2011/08/21)
-
- Cyanuric chloride catalysed rapid conversion of β-ketoesters into β-enaminoesters under mild and solvent-free conditions
-
Cyanuric chloride is shown to be an extremely efficient catalyst for the synthesis of β-enaminoesters from β-ketoesters under solvent-free conditions by grinding in a mortar with pestle at 25 °C. A short reaction time, an inexpensive and easily available catalyst, mild reaction conditions and excellent yields of the products are attractive features of this methodology.
- Kamble,Joshi,Atkore
-
experimental part
p. 616 - 621
(2012/07/03)
-
- Ca(CF3COO)2: An efficient Lewis acid catalyst for chemo- and regio-selective enamination of β-dicarbonyl compounds
-
A relevant procedure has been developed for the synthesis of β-enaminoesters catalysed by Ca(CF3COO)2. The reaction of β-ketoesters with primary amines was efficiently carried out under solvent-free conditions at room temperature and led to chemo- and regio-selective formations of enamine derivatives in high yields.
- Harrad, Mohamed Anoir,Outtouch, Rachid,Ait Ali, Mustapha,Firdoussi, Larbi El,Karim, Abdallah,Roucoux, Alain
-
experimental part
p. 442 - 446
(2010/11/21)
-
- A green solventless protocol for the synthesis of β-Enaminones and β -Enamino esters using silica sulfuric acid as a highly efficient, heterogeneous and reusable catalyst
-
Silica sulfuric acid is utilized as a green, highly efficient, heterogeneous and recyclable catalyst for the preparation of β-enaminones and β -enamino esters from amines and β -dicarbonyl compounds under solvent-free conditions at 80 °C. Using this method, the title compounds are produced in high to excellent yields and in short reaction times.
- Hasaninejad, Alireza,Zare, Abdolkarim,Mohammadizadeh, Mohammad Reza,Shekouhy, Mohsen,Moosavi-Zare, Ahmad Reza
-
experimental part
p. 1546 - 1554
(2011/12/05)
-
- Hydrogenation of β-N-substituted and β-N,N-disubstituted enamino esters in the presence of iridium(I) catalyst
-
Several new β-amino esters were prepared in two simple steps from β-keto ester derivatives and primary and secondary amines under mild conditions. The hydrogenation of various enamino esters was performed at 50°C in the presence of iridium catalysts. The new β-N-substituted amino esters were isolated in high yields. Georg Thieme Verlag Stuttgart.
- Hebbache, Hania,Hank, Zakia,Bruneau, Christian,Renaud, Jean-Luc
-
experimental part
p. 2627 - 2633
(2009/12/06)
-
- K7[PW11CoO40]: Efficient and ecofriendly catalyst for the enamination of β-dicarbonyl compounds
-
Condensation of a variety of β-dicarbonyl compounds with primary and secondary amines carried out in the presence of catalytic amounts of K7[PW11CoO40]. From this reaction N-substituted β-enamino esters and ketones were obtained in high yields. Copyright
- Oskooie, Hossein A.,Heravi, Majid M.,Javadi, Negar M.,Bakhtiari, Khadijeh,Bamoharram, Fatemeh F.
-
p. 2864 - 2869
(2008/12/22)
-
- Palladium-catalyzed oxidative cyclization of N-aryl enamines: From anilines to indoles
-
(Chemical Equation Presented) The special advantage of the title reaction to form substituted indoles 2 lies within the broad scope of the transformation: A multitude of N-aryl enaminones 1 can be prepared readily in one step from commercially available anilines. Furthermore, anilines can be converted directly in a one-pot process into the indole products. R1 = H, Me, OMe, Cl, F, carbonyl functionality, CN, fused aryl; R2 = alkyl, aryl; R 3 = alkyl, O-alkyl.
- Wuertz, Sebastian,Rakshit, Souvik,Neumann, Julia J.,Droege, Thomas,Glorius, Frank
-
supporting information; experimental part
p. 7230 - 7233
(2009/04/10)
-
- ZrCl4-catalyzed efficient synthesis of enaminones and enamino esters under solvent-free conditions
-
A facile synthesis of β-enaminones and enamino esters by condensation of β-dicarbonyl compounds with differently substituted amines in the presence of ZrCl4 under solvent-free conditions is reported.
- Lin, Jin,Zhang, Li-Feng
-
-
- Enamination of 1,3-dicarbonyl compounds catalyzed by tin tetrachloride
-
Tin tetrachloride has been found to be an extremely efficient catalyst for the enamination of 1,3-dicarbonyl compounds under solvent-free conditions at room temperature.
- Zhang, Zhan-Hui,Ma, Zi-Chuan,Mo, Li-Ping
-
p. 535 - 539
(2008/09/18)
-
- Efficient synthetic method for β-Enamino esters catalyzed by Yb(OTf)3 under solvent-free conditions
-
A wide range of ?-enamino esters have been synthesized in moderate to excellent yields by reacting 1,3-dicarbonyl compounds with amines in the presence of catalytic amounts of Yb(OTf)3 (2 mol%). The reaction proceeds smoothly at ambient temperature under solvent-free conditions. The catalyst can be recovered and reused. CSIRO 2006.
- Varala, Ravi,Nuvula, Sreelatha,Adapa, Srinivas R.
-
p. 921 - 924
(2007/10/03)
-
- A general and efficient method for the preparation of β-enamino ketones and esters catalyzed by indium tribromide
-
A variety of β-enamino ketones and esters have been synthesized in high to exellent yields by reacting β-dicarbonyl compounds with amines in the presence of a catalytic amount of indium tribromide. The reaction proceeds smoothly at room temperature in a short reaction time under solvent-free conditions.
- Zhang, Zhan-Hui,Yin, Liang,Wang, Yong-Mei
-
p. 184 - 190
(2007/10/03)
-
- A solvent-free synthesis of β-amino-α,β-unsaturated ketones and esters catalysed by sulfated zirconia
-
β-Amino-α,β-unsaturated ketones and esters are synthesised by the condensation of β-dicarbonyl compounds with amines in the presence of a solid superacid sulfated zirconia (SO42-/ZrO 2, SZ) under solvent-free conditions.
- Zhang, Zhan-Hui,Song, Li-Ming
-
p. 817 - 820
(2007/10/03)
-
- Efficient rhodium-catalyzed asymmetric hydrogenation for the synthesis of a new class of N-aryl β-amino acid derivatives
-
(Chemical Equation Presented) N-Aryl β-amino esters were obtained by asymmetric hydrogenation of a new class of N-aryl β-enamino esters. High conversions and up to 96.3% ee values were achieved with a Rh-TangPhos catalyst.
- Dai, Qian,Yang, Weiran,Zhang, Xumu
-
p. 5343 - 5345
(2007/10/03)
-
- Self-condensation of (β-Alkoxycarbonylalkylidene)ammonium Salts
-
Iminium chlorides or trifluoroacetates of type 2, formed by protonation of β-(alkoxycarbonyl)-enamines 1, have been proved to undergo condensation to give derivatives of 4-alkyl-2-amino-6-hydroxybenzoic acid 6 via elimination of ammonium salt and alcohol.The structures of 6 had been established by spectroscopic data as well as by further reactions.The range of application of this condensation reaction has been studied and the mechanism is discussed.In the primary step presumably a nucleophilic attack on the alkoxycarbonyl group of the iminium salt 2 takes place by the enamine 1 present in the equilibrium.Analogous reactions are also found for homologues of the enamine 1 (e.g. 11, 13 and 17) to give the condensation products 12, 14, 15, and 20.
- Boehme, Horst,Graetz, Jochen Graetzel von,Martin, Fred,Matusch, Rudolf,Nehne, Joerg
-
p. 394 - 402
(2007/10/02)
-