- Development of a 1,2,4-Triazole-Based Lead Tankyrase Inhibitor: Part II
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Tankyrase 1 and 2 (TNKS1/2) catalyze post-translational modification by poly-ADP-ribosylation of a plethora of target proteins. In this function, TNKS1/2 also impact the WNT/β-catenin and Hippo signaling pathways that are involved in numerous human diseas
- Aertssen, Sjoerd,Amundsen-Isaksen, Enya,Brinch, Shoshy Alam,Damen, Eddy,Galera-Prat, Albert,Krauss, Stefan,Leenders, Ruben G. G.,Murthy, Sudarshan,Nieczypor, Piotr,Smits, Johannes N.,Sowa, Sven T.,Waaler, Jo,Wegert, Anita,Lehti?, Lari,Nazaré, Marc
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p. 17936 - 17949
(2021/12/17)
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- Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids
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A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.
- Tang, Jing-Jing,Yu, Xiaoqiang,Yamamoto, Yoshinori,Bao, Ming
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p. 13955 - 13961
(2021/11/20)
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- Chromium-catalyzed ligand-free amidation of esters with anilines
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Amides are important structural motifs in pharmaceutical and agrochemical chemistry because of the intriguing biological active properties. We report here the amidation of commercially available esters with anilines that was promoted by low-cost and air-stable chromium(III) pre-catalyst combined with magnesium, providing access to amides. This reaction occurs without the use of external ligands in a simple operation. Mechanistic studies indicate that a reactive aminated Cr species responsible for the amidation can be considered, which may be formed by reaction of low-valent Cr with aniline followed by reduction with hydrogen evolution.
- Chen, Changpeng,Ling, Liang,Luo, Meiming,Zeng, Xiaoming
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supporting information
p. 762 - 766
(2021/04/14)
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- Para -Selective copper-catalyzed C(sp2)-H amidation/dimerization of anilides via a radical pathway
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Copper-catalyzed amidation/dimerization of anilides via regioselective C(sp2)-H functionalization is achieved. The para-selective amidation is accomplished on the anilide aromatic ring via a radical pathway leading to C-N bond formation in the presence of ammonium persulfate as a radical source/oxidant for the copper catalyst. The developed protocol tolerates a wide range of anilide substrates. The regioselectivity is confirmed by single-crystal X-ray studies.
- Viveki, Amol B.,Garad, Dnyaneshwar N.,Gonnade, Rajesh G.,Mhaske, Santosh B.
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supporting information
p. 1565 - 1568
(2020/02/13)
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- Palladium-Catalyzed Amide Synthesis via Aminocarbonylation of Arylboronic Acids with Nitroarenes
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A palladium-catalyzed aminocarbonylation of aryl boronic acids with nitroarenes for the synthesis of amides has been developed. A wide range of substrates were well-tolerated and gave the corresponding amides in moderate to good yields. No external oxidant or reductant was needed in this procedure. This procedure provides a redox-economical process for the synthesis of amides.
- Peng, Jin-Bao,Li, Da,Geng, Hui-Qing,Wu, Xiao-Feng
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supporting information
p. 4878 - 4881
(2019/06/17)
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- Solvent- and transition metal-free amide synthesis from phenyl esters and aryl amines
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A general, economical, and environmentally friendly method of amide synthesis from phenyl esters and aryl amines was developed. This new method has significant advantages compared to previously reported palladium-catalyzed approaches. The reaction is performed transition metal- and solvent-free, using a cheap and environmentally benign base, NaH. This approach enabled us to obtain target amides in high yields with high atom economy.
- Rzhevskiy, Sergey A.,Ageshina, Alexandra A.,Chesnokov, Gleb A.,Gribanov, Pavel S.,Topchiy, Maxim A.,Nechaev, Mikhail S.,Asachenko, Andrey F.
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p. 1536 - 1540
(2019/01/24)
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- Method for synthesizing amide compound through photocatalysis in water phase
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The invention discloses a method for synthesizing an amide compound through photocatalysis in a water phase. The method comprises the following steps: putting catalysis amounts of a free radical initiator, an amine derivative, a carboxylic acid derivative, a phase transfer catalyst, an inorganic base and water into a reaction container, carrying out a reaction in a photocatalysis reaction instrument at certain power under a room temperature condition, after a certain time, carrying out extraction by using a small amount of ethyl acetate, and carrying out recrystallization, so as to obtain theamide compound, wherein the free radical initiator is eosin, methyl orange, sodium persulfate, ammonium persulfate or potassium peroxodisulfate, the phase transfer catalyst is tetrabutylammonium bromide, and the power of the photocatalytic reaction instrument is 5W. By adopting the method disclosed by the invention, toxic thionyl chloride or phosphorus oxychloride is not needed for a chlorinationreaction, water is adopted as a solvent, a novel photocatalysis method is used, and the amide compound with a high yield can be prepared through a room-temperature reaction for 2-5 hours with an incandescent light bulb of 5W, and in addition, the method is simple in aftertreatment, and low in cost and is an ideal green synthesis method of amide compounds.
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Paragraph 0061
(2019/10/01)
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- Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer
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Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.
- Xu, Ze-Ming,Li, Hong-Xi,Young, David James,Zhu, Da-Liang,Li, Hai-Yan,Lang, Jian-Ping
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supporting information
p. 237 - 241
(2019/01/10)
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- Amide-assisted radical strategy: Metal-free direct fluorination of arenes in aqueous media
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A metal- and initiator-free direct fluorination of arenes with the assistance of an amide group is developed. This reaction proceeded under simple aqueous conditions with good functional group tolerance and ortho-para selectivity, and is highly practical because it could be readily scaled up to a multigram-scale. At this stage, an exclusive mechanism could not be proposed, and several possibilities have been discussed. The possibility of the amide-assisted radical chain mechanism has been supported by experimental and computational investigations as well as a seminal work.
- Liang, Deqiang,Li, Yanni,Gao, Shulin,Li, Renlun,Li, Xiangguang,Wang, Baoling,Yang, Hai
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supporting information
p. 3344 - 3349
(2017/07/28)
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- Efficient synthesis of amides and esters from alcohols under aerobic ambient conditions catalyzed by a Au/mesoporous Al2O3 nanocatalyst
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An efficient heterogeneous Au/mesoporous alumina nanocatalyst has been successfully developed for the synthesis of amides and esters from simple building blocks of readily available alcohols and amines. The processes were simple and were performed at room temperature and atmospheric pressure of O2 to form the desired products with up to 97% isolated yield. The ability of Au/mesoporous alumina to catalyze these reactions under ambient conditions further enhances the sustainability of these chemical processes. Furthermore, the nanocatalyst was stable to air and water and could be recovered and reused easily. The enhanced catalytic activity of Au/mesoporous alumina might be attributed to the presence of negatively charged Au nanoparticles that could promote oxidation processes as well as the stability of the mesoporous alumina support calcined at a high temperature of 800°C. Gold for green: Gold nanoparticles supported on mesoporous alumina catalyze the efficient synthesis of amides and esters from simple building blocks of readily available alcohols and amines under ambient aerobic reaction conditions (R1=aryl, alkyl, and R2=H, alkyl).
- Chng, Leng Leng,Yang, Jinhua,Ying, Jackie Y.
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p. 1916 - 1925
(2015/06/16)
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- Copper-catalyzed oxidative amidation between aldehydes and arylamines under mild conditions
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A facile strategy to prepare amide bonds has been developed. A series of amide compounds, including heterocyclic amide compounds, were obtained with moderate to good yields ranging from 31-88% by using copper iodide (CuI) to catalyze the oxidative amidation between aldehydes and amines under solvent-free conditions at room temperature in air.
- Ding, Yongzheng,Zhang, Xian,Zhang, Dongyang,Chen, Yuting,Wu, Zhibing,Wang, Peiyi,Xue, Wei,Song, Baoan,Yang, Song
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supporting information
p. 831 - 833
(2015/02/19)
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- CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acids with amides and anilines
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CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acid with amide has been developed, leading to N-arylamides in modest to excellent yields. Anilines bearing electron-withdrawing substituents could also couple efficiently
- Sheng, Wei-Jian,Ye, Qing,Yu, Wu-Bin,Liu, Ren-Rong,Xu, Meng,Gao, Jian-Rong,Jia, Yi-Xia
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supporting information
p. 599 - 601
(2015/02/19)
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- Efficient cobalt-catalyzed C-N cross-coupling reaction between benzamide and aryl iodide in water
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A practical and efficient strategy for the N-arylation of benzamide catalysed by a Co(C2O4)·2H2O/dmeda system in water is reported. Under the optimized conditions, a wide variety of N-arylated products were obtained in good yields (up to 92%) using substituted aryl iodides.
- Tan, Bryan Yong-Hao,Teo, Yong-Chua
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supporting information
p. 7478 - 7481
(2014/12/11)
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- Copper catalyzed N-arylation between aryl halides and nitriles in water: An efficient tandem synthesis of benzanilides
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A series of benzanilide compounds were synthesized through copper-catalyzed tandem reactions. With the assistance of ionic liquid as phase transfer catalyst, aryl halides, and nitriles underwent a hydrolysis/coupling pathway to form benzanilides in water. Advantages of this reaction include the use of water as the environmental friendly solvent, short reaction time, and the tolerance of various functional groups. A proposed mechanism based on control experiments is also presented.
- Wang, Jichao,Yin, Xinchi,Wu, Jun,Wu, Datong,Pan, Yuanjiang
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p. 10463 - 10469
(2013/11/19)
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- Direct N-cyclopropylation of secondary acyclic amides promoted by copper
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The N-cyclopropylation of aromatic and aliphatic secondary acyclic amides, known to be poor nucleophiles, has been accomplished using a simple and cheap copper system. The corresponding tertiary acyclic amides, which constitute a wide family of biologically active compounds, have been obtained in good to excellent yields.
- Racine, Emilie,Monnier, Florian,Vors, Jean-Pierre,Taillefer, Marc
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supporting information
p. 7412 - 7414
(2013/09/23)
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- Pd(OAc)2-catalyzed carbonylative coupling of aryl iodide with ortho-haloamines in water
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The carbonylative cross coupling of aryl iodide with ortho-haloaniline to ortho-haloanilide using phosphine-free Pd(OAc)2 catalyst in water as a reaction medium has been studied. The present protocol facilitated the reaction of o-haloanilines with a wide variety of hindered and functionalized aryl iodides, affording good yields of the desired products. The protocol was also extended for the synthesis of benzoxazoles through cyclization of ortho-haloanilide using Cu(acac)2 catalyst. Taylor & Francis Group, LLC.
- Tambade, Pawan J.,Patil, Yogesh P.,Qureshi, Ziyauddin S.,Dhake, Kishor P.,Bhanage, Bhalchandra M.
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supporting information; experimental part
p. 176 - 185
(2011/10/31)
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- A simple copper-catalyzed synthesis of tertiary acyclic amides
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The N-arylation of aromatic and aliphatic secondary acyclic amides, known to be poor nucleophiles, has been accomplished using a simple and cheap copper catalytic system. The corresponding tertiary acyclic amides, which can be found in numerous biologically active compounds, have been obtained in good to excellent yields.
- Racine, Emilie,Monnier, Florian,Vors, Jean-Pierre,Taillefer, Marc
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supporting information; experimental part
p. 2818 - 2821
(2011/07/09)
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- Bis(cyclopentadienyldicarbonyliron) as a convenient carbon monoxide source in palladium-catalyzed carbonylative coupling of aryl iodides with amines, alcohols, and thiols
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Bis(cyclopentadienyldicarbonyliron) ([CpFe(CO)2]2) serves as a carbon monoxide source in carbonylative coupling reactions. Treatment of aryl iodides with primary amines in the presence of DBU and [CpFe(CO)2]2 under palladium catalysis provides the corresponding benzamides in good yields. Similar reactions with phenols and thiols provide the corresponding benzoate esters and thioesters, respectively. A catalytic amount of DMAP as an additive promoted the carbonylative coupling reactions with primary alcohol and secondary amine.
- Nakaya, Ryotaro,Yorimitsu, Hideki,Oshima, Koichiro
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experimental part
p. 904 - 906
(2011/12/05)
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- Use of molecular oxygen as a reoxidant in the synthesis of 2-substituted benzothiazoles via palladium-catalyzed C-H functionalization/intramolecular C-S bond formation
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Molecular oxygen (O2) was successfully employed as a reoxidant in cyclizations of thiobenzanilides 1a-s through a palladium-catalyzed C-H functionalization/intramolecular C-S bond formation process, leading to an efficient, green method for the synthesis of 2-arylbenzothiazoles 2a-s. Addition of cesium fluoride (CsF) greatly enhanced the reactions, which produced variously substituted 2-arylbenzothiazoles with good functional group tolerance. Thioureas 4a-j were also found to be suitable substrates for the cyclization process using a palladium/O2 catalyst system, thus generating 2-aminobenzothiazoles 5a-j. One-pot syntheses of 2-aminobenzothiazoles 5a-j from aryl isothiocyanates 6 and amines 7 were also successful.
- Inamoto, Kiyofumi,Hasegawa, Chisa,Kawasaki, Junpei,Hiroya, Kou,Doi, Takayuki
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experimental part
p. 2643 - 2655
(2010/12/25)
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- Pd(OAc)2-catalyzed aminocarbonylation of aryl iodides with aromatic or aliphatic amines in water
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An efficient ligand-free protocol has been developed for the amincocarbonylation of aryl iodides with aromatic/aliphatic amines using palladium(II) acetate as a catalyst in water under milder operating conditions. The system tolerated a wide variety of hindered and functionalized aryl iodides/amines and afforded the desired amides in excellent yields at low catalyst concentration. Georg Thieme Verlag Stuttgart.
- Tambade, Pawan J.,Patil, Yogesh P.,Bhanushali, Mayur J.,Bhanage, Bhalchandra M.
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experimental part
p. 2347 - 2352
(2009/04/04)
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- A series of new zirconium complexes bearing bis(phenoxyketimine) ligands: Synthesis, characterization and ethylene polymerization
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A series of new zirconium complexes bearing bis(phenoxyketimine) ligands, bis((3,5-di-tert-butyl-C6H2-2-O)R1CN (2-R 2-C6H4))ZrCl2 {R1 = Me, R2 = H (2a); R1 = Et, R2 = H (2b); R 1 = Ph, R2 = H (2c); R1 = 2-Me-Ph, R 2 = H (2d); R1 = 2-F-Ph, R2 = H (2e); R 1 = 2-Cl-Ph, R2 = H (2f); R1 = 2-Br-Ph, R 2 = H (2g); R1 = Ph, R2 = Me (2h); R 1 = Ph, R2 = F (2i)}, have been prepared, characterized and tested as catalyst precursors for ethylene polymerization. Crystal structure analysis reveals that complex 2c has a six coordinate center in a distorted octahedral geometry with trans-O, cis-N, cis-Cl arrangement which possesses approximate C2 symmetry. When activated with methylaluminoxane (MAO), complexes 2a-2i exhibited high ethylene polymerization activities of 10 6-108 g PE (mol M h)-1. Compared with the bis(phenoxyimine) zirconium analogues bis((3,5-di-tert-butyl-C6H 2-2-O)CHNC6H5)ZrCl2 (3), the introduction of substituent on the carbon atom of the imine double bond enhanced the catalytic activity and molecular weight of prepared polyethylene. Especially, when the H atom at the carbon atom of the imine double bond was replaced by 2-fluoro-phenyl with strong electronic-withdrawing property, complex 2e displayed the highest catalytic activity, and the polyethylene obtained possessed the highest molecular weight and melt point.
- Chen, Shangtao,Zhang, Xiaofan,Ma, Hongwei,Lu, Yingying,Zhang, Zhicheng,Li, Huayi,Lu, Zhanxia,Cui, Nannan,Hu, Youliang
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p. 4184 - 4191
(2007/10/03)
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- PLA2 inhibitors and their use for inhibition of intestinal cholesterol absorption
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Certain compounds have been synthesized and found to be effective inhibitors of phospholipase A2 (PLA2), and thereby useful in the treatment of intestinal cholesterol absorption and the disease states arising therefrom, such as hyper
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