- A tandem highly stereoselective FeCl3-promoted synthesis of a bisindoline: Synthetic utility of radical cations in heterocyclic construction
-
A conceptually distinctive stereoselective construction of the novel dimer, N-[N′-acetyl-7,7′-bis-(3,4-dimethoxy-phenyl)-7,8,7′,8′- tetrahydro-N′H-[8,8′]biindolyl-N-yl]-ethanone 25 (bisindoline) is described below. These structures, which include 7-(3,4-dimethoxyphenyl)- indoline 24 (veratryl indoline), were obtained by the tactical combination of palladium-catalysed coupling which produced 10-acetamido-3,4-dimethoxystilbene 9, followed by FeCl3 induced oxidative cyclization/dimerization. All new structures were fully characterized by 1- and 2D NMR spectroscopy, (proton, carbon-13, COSY, HMBC, HMQC) and mass spectrometry. Configurational assignments were further supported by semi-empirical AM1 calculations. Mechanistic interpretations, consistent with our results, are discussed. Graphical Abstract
- Thomas, Noel F.,Velu, Saraswati S.,Weber, Jean-Frédéric F.,Lee,Hadi, A. Hamid A.,Richomme, Pascal,Rondeau, David,Noorbatcha, Ibrahim,Awang, Khalijah
-
-
Read Online
- Synthesis, Biological Evaluation of ortho-Carboxamidostilbenes as Potential Inhibitors of Hyperglycemic Enzymes, and Molecular Docking Study
-
A new series of ortho-carboxamidostilbenes derivatives were synthesized via Heck Coupling and screened for their α-amylase and α-glucosidase inhibitory potential. The results indicated that all the synthesized compounds showed a substantial α-glucosidase
- Abu Bakar, Mohamad Hafizi,Awang, Khalijah,Azmi, Mohamad Nurul,Che Omar, Mohammad Tasyriq,Mohamad, Norhadi,Phua, Yoong Hui,Supratman, Unang,Wahab, Habibah A.
-
-
- Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines
-
Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.
- Chen, Yujie,Huang, Zhibin,Jiang, Yaqiqi,Shu, Sai,Yang, Shan,Shi, Da-Qing,Zhao, Yingsheng
-
p. 8226 - 8235
(2021/06/28)
-
- Nickel(II)- And Silver(I)-Catalyzed C-H Bond Halogenation of Anilides and Carbamates
-
ortho -C-H bond halogenation of anilides and N -aryl carbamates using easily available N -halosuccinimides (NXS) as the active halogenation reagent in the presence of nickel or silver catalyst has been developed. This method provides a new approach to 2-haloanilides and carbamates, which may serve as starting materials for the synthesis of pharmaceutically and biologically active compounds.
- Kianmehr, Ebrahim,Afaridoun, Hadi
-
p. 1513 - 1523
(2020/12/14)
-
- Complementary Site-Selective Halogenation of Nitrogen-Containing (Hetero)Aromatics with Superacids
-
Site-selective functionalization of arenes that is complementary to classical aromatic substitution reactions remains a long-standing quest in organic synthesis. Exploiting the generation of halenium ion through oxidative process and the protonation of the nitrogen containing function in HF/SbF5, the chlorination and iodination of classically inert Csp2?H bonds of aromatic amines occurs. Furthermore, the superacid-promoted (poly)protonation of the molecules acts as a protection, favoring the late-stage selective halogenation of natural alkaloids and active pharmaceutical ingredients.
- Mamontov, Alexander,Martin-Mingot, Agnès,Métayer, Benoit,Karam, Omar,Zunino, Fabien,Bouazza, Fodil,Thibaudeau, Sébastien
-
supporting information
p. 10411 - 10416
(2020/07/30)
-
- TRICYCLIC CRBN LIGANDS AND USES THEREOF
-
The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.
- -
-
Paragraph 0696; 0885; 0886
(2020/01/24)
-
- Lewis Acid Catalyzed Atom-Economic Synthesis of C2-Substituted Indoles from o-Amido Alkynols
-
Herein we have disclosed a Zn(OTf)2 catalyzed synthesis of C2-alkyl substituted indole derivatives via unprecedented carbonyl group migration from o-amido alkynols. The key features of this protocol involve N,O-carbonyl group migration, broad s
- Garkhedkar, Amol Milind,Gore, Babasaheb Sopan,Hu, Wan-Ping,Wang, Jeh-Jeng
-
supporting information
p. 3531 - 3536
(2020/04/20)
-
- Nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy
-
Herein reported is a nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy by using simple and readily available thioesters. In contrast to traditional activation of weaker C(acyl)-S bond, the C(acyl)-C bond of
- Feng, Yunxia,Yang, Shimin,Zhao, Shen,Zhang, Dao-Peng,Li, Xinjin,Liu, Hui,Dong, Yunhui,Sun, Feng-Gang
-
supporting information
p. 6734 - 6738
(2020/09/15)
-
- Iridium-catalyzed intramolecular C–N and C–O/S cross-coupling reactions: Preparation of benzoazole derivatives
-
The irdium-catalyzed intramolecular arylcarbon-hetero cross-coupling reactions with o-haloarylamides or o-haloarylamidine have been effectively achieved using KOAc and just 1 mol% catalyst. The [Ir(cod)Cl]2 was proved to be more potential for smoothly assembling functional structures benzimidazoles, benzoxazoles and benzothiazoles, which was superior to Cu- and Pd-catalyzed systems. Simultaneously, a concise and efficient synthesis of tafamidis was developed in 5-g scale.
- Shi, Yajie,Zhou, Qifan,Du, Fangyu,Fu, Yang,Du, Yang,Fang, Ting,Chen, Guoliang
-
supporting information
(2019/09/10)
-
- Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions
-
The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.
- Costello, Jeff P.,Ferreira, Eric M.
-
supporting information
p. 9934 - 9939
(2019/12/24)
-
- Synthesis of Arylamides via Ritter-Type Cleavage of Solid-Supported Aryltriazenes
-
A novel route for the synthesis of N-arylamides via the cleavage of aryltriazenes with alkyl or aryl nitriles is presented. We developed a variation of the Ritter reaction that allows the use of acetonitrile as solvent and reagent in reactions with solid-supported precursors. The reaction was optimized for the generation of N-aryl acetamides using a diverse range of immobilized building blocks including o-, m-, and p-substituted aryltriazenes. The cleavage via the Ritter-type conversion was combined with an on-bead cross-coupling reaction of halogen-substituted aryltriazenes with pyrazoles. Additionally, the synthesis of on-bead generated arylboronic ester-substituted triazenes was shown. The developed procedure was further expanded to use other commercially available nitriles, such as acrylonitrile, benzonitrile, and chlorinated alkyl nitriles as suitable reagents for a Ritter-type cleavage of the prepared triazene linkers.
- Wippert, Nicolai A.,Jung, Nicole,Br?se, Stefan
-
supporting information
p. 568 - 572
(2019/09/03)
-
- PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles
-
An efficient synthesis of N-acetyl-2-substituted indole derivatives via direct intramolecular hydroamination of N-acetyl-2-alkynylaniline derivatives was developed. The reaction could be applied to a wide range of substrates employing only 1–2 mol% of PtCl4 as the catalyst to furnish the desired indole products in moderate to excellent yields. The current protocol is efficient, reliable and scalable, and could serve as an important tool for convenient and rapid access to this important class of N-heterocyclic skeleton from readily available substrates.
- Chaisan, Nattawadee,Kaewsri, Wilailak,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
-
supporting information
p. 675 - 680
(2018/01/18)
-
- Palladium-Catalyzed Domino Allenamide Carbopalladation/Direct C-H Allylation of Heteroarenes: Synthesis of Primprinine and Papaverine Analogues
-
Palladium-catalyzed intramolecular carbopalladation onto allenamides completed by direct C-H allylation of heterocycles is studied. The domino construction/heteroarylation of isoquinolone process is first achieved. A general three-step one-pot strategy, i
- Hédouin, Jonathan,Schneider, Cédric,Gillaizeau, Isabelle,Hoarau, Christophe
-
supporting information
p. 6027 - 6032
(2018/10/05)
-
- Carboiodination Catalyzed by Nickel
-
A novel nickel-catalyzed cycloisomerization reaction forming a new carbon-carbon bond while preserving the carbon-halogen bond has been developed. A cheap and readily available Ni-catalyst is employed to generate nitrogen containing heterocycles in good t
- Yoon, Hyung,Marchese, Austin D.,Lautens, Mark
-
supporting information
p. 10950 - 10954
(2018/09/11)
-
- Metal-free formal synthesis of phenoxazine
-
A transition metal-free formal synthesis of phenoxazine is presented. The key step of the sequence is a high-yielding O-arylation of a phenol with an unsymmetrical diaryliodonium salt to provide an ortho-disubstituted diaryl ether. This species was cyclized to acetylphenoxazine in moderate yield. The overall yield in the three-step sequence is 72% based on recovered diaryl ether. An interesting, unusually stable iodine(III) intermediate in the O-arylation was observed by NMR and could be converted to the product upon longer reaction time.
- Kervefors, Gabriella,Becker, Antonia,Dey, Chandan,Olofsson, Berit
-
supporting information
p. 1491 - 1497
(2018/07/05)
-
- Highly Chemo- and Stereoselective Catalyst-Controlled Allylic C?H Insertion and Cyclopropanation Using Donor/Donor Carbenes
-
The highly chemo-, enantio-, and diastereoselective catalyst-controlled intramolecular allylic C?H insertion and cyclopropanation of donor/donor carbenes are reported. The RuII/Pybox complex selectively catalyzed the intramolecular allylic C?H
- Zhu, Dong,Chen, Lianfen,Zhang, He,Ma, Zhiqiang,Jiang, Huanfeng,Zhu, Shifa
-
supporting information
p. 12405 - 12409
(2018/09/18)
-
- Cobalt(II)-catalyzed regioselective C-H halogenation of anilides
-
A cobalt-catalyzed regioselective C-H halogenation methodology is reported herein. The highlight of this work is the highly selective C-H functionalization of anilides, which results in high-yielding, versatile, and practical halogenated products. Thereby, brominations, chlorinations and iodinations of many electron-rich and electron-deficient anilides were achieved in a highly selective fashion. Mechanistic studies with respect to the pathway of the reaction are also described.
- Li, Ze-lin,Sun, Kang-kang,Cai, Chun
-
supporting information
p. 5433 - 5440
(2018/08/12)
-
- Palladium-Mediated Site-Selective C-H Radio-iodination
-
The palladium-mediated C-H radio-iodination of arenes using sodium iodide as the primary isotopic source is reported and performed without chemical know-how in 30 min and applied to the synthesis of complex radio-iodinated compounds of biological interest.
- Dubost, Emmanuelle,Babin, Victor,Benoist, Florian,Hébert, Alexandra,Barbey, Pierre,Chollet, Céline,Bouillon, Jean-Philippe,Manrique, Alain,Pieters, Grégory,Fabis, Frédéric,Cailly, Thomas
-
supporting information
p. 6302 - 6305
(2018/10/02)
-
- Palladium-catalyzed ortho-halogenations of acetanilides with N-halosuccinimides via direct sp2 C–H bond activation in ball mills
-
A solvent-free palladium-catalyzed ortho-iodination of acetanilides using N-iodosuccinimide as the iodine source has been developed under ball-milling conditions. This present method avoids the use of hazardous organic solvents, high reaction temperature,
- Liu, Zi,Xu, Hui,Wang, Guan-Wu
-
supporting information
p. 430 - 435
(2018/02/27)
-
- Synthesis of 2-methylbenzoxazoles directly from: N -phenylacetamides catalyzed by palladium acetate
-
A method to synthesize 2-methylbenzoxazoles directly from N-phenylacetamides catalyzed by Pd(OAc)2 in the presence of K2S2O8 and TfOH has been developed. The desired products were obtained in moderate to excellent yields. This approach provides a facile procedure to prepare benzoxazoles with available substrates. It is found that TfOH is the key factor for this cyclization reaction. A plausible mechanism of the reaction is proposed according to the control reactions and the literature.
- Wang, Biying,Jiang, Chengfei,Qian, Jiasheng,Zhang, Shuwei,Jia, Xiaodong,Yuan, Yu
-
p. 101 - 107
(2017/12/27)
-
- Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature
-
Despite the wide use of aryl radicals in organic synthesis, current methods to prepare them from aryl halides, carboxylic acids, boronic acids, and diazonium salts suffer from limitations. Aryl triflates, easily obtained from phenols, are promising aryl radical progenitors but remain elusive in this regard. Inspired by the single electron transfer process for aryl halides to access aryl radicals, we developed a simple and efficient protocol to convert aryl triflates to aryl radicals. Our success lies in exploiting sodium iodide as the soft electron donor assisted by light. This strategy enables the scalable synthesis of two types of important organic molecules, i.e., aryl boronates and aryl iodides, in good to high yields, with broad functional group compatibility in a transition-metal-free manner at room temperature. This protocol is anticipated to find potential applications in other aryl-radical-involved reactions by using aryl triflates as aryl radical precursors.
- Liu, Wenbo,Yang, Xiaobo,Gao, Yang,Li, Chao-Jun
-
supporting information
p. 8621 - 8627
(2017/07/06)
-
- Monoprotected l-Amino Acid (l-MPAA), Accelerated Bromination, Chlorination, and Iodination of C(sp2)?H Bonds by Iridium(III) Catalysis
-
Halogenated arenes are important structural motifs commonly found in biologically active molecules and used for a variety of transformations in organic synthesis. Herein, we report the mono-protected l-amino acid (l-MPAA) accelerated iridium(III)-catalyzed halogenation of (hetero)anilides at room temperature. This reaction constitutes the first example of an iridium(III)/l-MPAA-catalyzed general halogenation of (hetero)arenes through C(sp2)?H activation. Furthermore, we demonstrate the potential utility of our method through its use in the synthesis of a quinolone derivative.
- Kathiravan, Subban,Nicholls, Ian A.
-
p. 7031 - 7036
(2017/05/29)
-
- Enantioselective Intramolecular C?H Insertion of Donor and Donor/Donor Carbenes by a Nondiazo Approach
-
The first enantioselective intramolecular C?H insertion and cyclopropanation reactions of donor- and donor/donor-carbenes by a nondiazo approach are reported. The reactions were conducted in a one-pot manner without slow addition and provided the desired
- Zhu, Dong,Ma, Jun,Luo, Kui,Fu, Hongguang,Zhang, Li,Zhu, Shifa
-
p. 8452 - 8456
(2016/07/19)
-
- Ligand-Free Heck Reactions of Aryl Iodides: Significant Acceleration of the Rate through Visible Light Irradiation at Ambient Temperature
-
A mild Heck reaction of aryl iodides and olefins was realized by the cooperation of a palladium and a photoredox catalyst under the irradiation of visible light. This protocol works well to synthesize stilbenes with high Z/E ratios and (E)-cinnamates in the absence of ligands at ambient temperature. Control experiments revealed that palladium salt, visible light and photoredox catalyst were all crucial for the achievement of this cross-coupling under mild conditions. (Figure presented.).
- Zhang, Heng,Huang, Xueliang
-
supporting information
p. 3736 - 3742
(2016/12/16)
-
- Synthesis of 2,3-Disubstituted Indoles and Benzofurans by the Tandem Reaction of Rhodium(II)-Catalyzed Intramolecular C-H Insertion and Oxygen-Mediated Oxidation
-
A highly effective and straightforward method to construct a wide range of functionalized 2,3-disubstituted indoles has been developed. The method involves the tandem reaction of rhodium(II)-catalyzed denitrogenative annulation of triazole-based benzyl an
- Shen, Hongjuan,Fu, Junkai,Yuan, Hao,Gong, Jianxian,Yang, Zhen
-
p. 10180 - 10192
(2016/11/17)
-
- Intermolecular coupling of 2-iodoanilides with benzoxazoles: Synthesis of N-(2-Benzoxazol-2-ylphenyl)benzamides via C-H activation
-
Using CuI/xantphos/Pd(OAc)2 catalytic system, the intermolecular C-C cross coupling between benzoxazoles and ortho-haloanilides has been developed in moderate to good yields. The procedure tolerates a series of functional groups on benzoxazole, such as ester, chloro, methyl, and methoxy groups. This divergent approach provides access to various N-(2-Benzoxazol-2-ylphenyl)amides.
- Sasmal, Swarnendu,Sen, Indira,Hall, Roger G.,Pal, Sitaram
-
supporting information
p. 1374 - 1377
(2015/03/04)
-
- Highly regioselective indoline synthesis under nickel/photoredox dual catalysis
-
Nickel/photoredox catalysis is used to synthesize indolines in one step from iodoacetanilides and alkenes. Very high regioselectivity for 3-substituted indoline products is obtained for both aliphatic and styrenyl olefins. Mechanistic investigations indic
- Tasker, Sarah Z.,Jamison, Timothy F.
-
supporting information
p. 9531 - 9534
(2015/08/18)
-
- A highly regioselective synthesis of N-acyl-2-acyl(aroyl)indolium Chloride through Palladium-Copper Catalysis Followed by Friedel-Crafts Reaction
-
2-Trimethylsilylethynyl acetanilides, obtained from the palladium-catalyzed reactions of 2-iodoacetanilides with trimethylsilylacetylene, underwent Friedel-Crafts acylation reactions yielding the N-acyl-2-acyl(aroyl)indolium chlorides in good yields. Georg Thieme Verlag Stuttgart New York.
- Khan, Md. Wahab,Akther, Arifa,Alam, Md. Shariful
-
p. 831 - 834
(2014/04/17)
-
- One-pot preparation of 2-(alkyl)arylbenzoselenazoles from the corresponding N-(acetyl)benzoyl-2-iodoanilines via a microwave-assisted methodology
-
We report here the first example of a one-pot synthesis of 2-(alkyl)arylbenzoselenazoles from N-(acetyl)benzoyl-2-iodoanilines. The reaction was carried out in the presence of Woollins' reagent under microwave irradiation and resulted in moderate to good yields.
- Redon, Sébastien,Kabri, Youssef,Crozet, Maxime D.,Vanelle, Patrice
-
supporting information
p. 5052 - 5054
(2015/01/09)
-
- 11a-N-Tosyl-5-deoxi-pterocarpan (LQB-223), a promising prototype for targeting MDR leukemia cell lines
-
Aza-deoxi-pterocarpans (1) were synthesized through palladium-catalyzed aza-arylation of dihydronaphtalen, and showed antineoplastic effect on MDR leukemic cell lines (K562, Lucena-1 and FEPS). Compounds 1c-d were prepared to identify the pharmacophoric g
- Buarque, Camilla D.,Salustiano, Eduardo J.,Fraga, Kevin C.,Alves, Bruna R.M.,Costa, Paulo R.R.
-
p. 190 - 197
(2014/04/17)
-
- Ti/Ni-mediated inter- and intramolecular conjugate addition of aryl and alkenyl halides and triflates
-
In this work, we show that the unique combination of a nickel catalyst and Cp2TiCl allows the direct conjugate addition of aryl and alkenyl iodides, bromides, and to a lesser extent, chlorides and triflates to α,β-unsaturated carbonyls at room temperature, without requiring the previous formation of an organometallic nucleophile. The reaction proceeds inter- and intramolecularly with good functional group compatibility, which is key for the development of free protecting group methodologies. Carbo- and heterocycles of five- and six-membered rings are obtained in good yields. Moreover, some insights about the mechanism involved have been obtained from cyclic voltammetry, UV-vis, and HRTEM measurements.
- Marquez, Irene R.,Miguel, Delia,Millan, Alba,Marcos, M. Luisa,De Cienfuegos, Luis Alvarez,Campana, Araceli G.,Cuerva, Juan M.
-
p. 1529 - 1541
(2014/03/21)
-
- Oxidative para- Triflation of acetanilides
-
Direct triflation of acetanilide derivatives with silver triflate has been accomplished under mild iodine(III)-mediated oxidative conditions. The reaction shows excellent regioselectivity for the para position and tolerates a range of ortho and meta substituents on the aromatic ring. This method is also compatible with the preparation of arylnonaflates in synthetically useful yields.
- Pialat, Amelie,Liegault, Benoit,Taillefer, Marc
-
supporting information
p. 1764 - 1767
(2013/06/26)
-
- Malonic ester amide synthesis: An efficient methodology for synthesis of amides
-
A general methodology malonic ester amide synthesis has been demonstrated, which uses α-substituted/unsubstituted diethyl malonates for the decarboxylative acylation of various aromatic/heteroaromatic primary/secondary amines to form one-carbon homologated amides, thus providing easy access to amides with odd/even chain lengths and an array of substituents on the alkyl/aryl part while avoiding use of acyl chlorides or peptide coupling reagents. Copyright
- Mahajan, Pankaj S.,Mahajan, Jyoti P.,Mhaske, Santosh B.
-
p. 2508 - 2516
(2013/07/25)
-
- Selectivity enhancement of aromatic halogenation reactions at the micellar interface: Effect of highly ionic media
-
Halogenation (iodination and bromination) of various aromatic compounds has been studied in micellar media in order to observe the effect on regioselectivity and conversion of the reaction. The addition of surfactant causes a change in the chemical shifts of the aromatic proton resonance of phenol which proves the orientation of the aromatic compound on the micellar surface. However, increase in ionic strength of the reaction media affects the selectivity of reaction by disturbing this spatial orientation of the aromatic compound in the micelle. Selectivity towards particular isomers is dependent on the concentration of the surfactant. In bromination of chlorobenzene (deactivated aromatic compound) enhancement in selectivity and conversion towards the para isomer has been observed.
- Samant, Bhupesh S.,Bhagwat, Sunil S.
-
scheme or table
p. 1039 - 1044
(2012/10/18)
-
- Nickel-catalysed aromatic Finkelstein reaction of aryl and heteroaryl bromides
-
A fast and efficient nickel-catalysed iodination reaction of aryl and heteroaryl bromides has been developed. The transformation was found to be general for a wide range of substrates and was used for the synthesis of iodo-PK11195, an imaging agent of Alzheimer's disease and iniparib, a compound used in the treatment of breast cancer.
- Cant, Alastair A.,Bhalla, Rajiv,Pimlott, Sally L.,Sutherland, Andrew
-
supporting information; experimental part
p. 3993 - 3995
(2012/06/05)
-
- Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications
-
The syntheses of fourteen unusual o-carboxamido stilbenes by the Heck protocol revealed surprising complexity related to intriguing substituent effects with mechanistic implications. The unexpected cytotoxic and chemopreventive properties also seem to be substituent dependent. For example, although stilbene 15d (with a 4-methoxy substituent) showed cytotoxicity on HT29 colon cancer cells with an IC50 of 4.9 μM, the 3,4-dimethoxy derivative (15c) is inactive. It is interesting to observe that the 3,5-dimethoxy derivative (15e) showed remarkable chemopreventive activity in WRL-68 fetal hepatocytes, surpassing the gold standard, resveratrol. The resveratrol concentration needed to be 5 times higher than that of 15e to produce comparable elevation of NQO1.
- Kee, Chin Hui,Ariffin, Azhar,Awang, Khalijah,Takeya, Koichi,Morita, Hiroshi,Hussain, Salmaan Inayat,Chan, Kok Meng,Wood, Pauline J.,Threadgill, Michael D.,Lim, Chuan Gee,Ng, Seikweng,Weber, Jean Frederic F.,Thomas, Noel F.
-
experimental part
p. 5646 - 5660
(2011/02/18)
-
- A straightforward synthesis of benzothiazines
-
(Chemical Equation Presented) A series of 4H-3,1-benzothiazines have been successfully synthesized through a three-step sequence starting from commercially available 2-iodoaniline. The key step consists of the cyclization of compounds 6 via an intramolecu
- Gimbert, Carolina,Vallribera, Adelina
-
supporting information; experimental part
p. 269 - 271
(2009/08/08)
-
- A FeCl3-promoted highly atropodiastereoselective cascade reaction: synthetic utility of radical cations in indolostilbene construction
-
The FeCl3-promoted oxidative cyclization/coupling of acetamidostilbenes possessing 3-methoxy, 4-methoxy and 3,5-methoxy substitutions (21), (22) and (23) is described. Only 3,5-substitution gave rise to novel indolostilbenes, each possessing two stereogenic axes (axially chiral but racemic dimers (39) and (40)). The 4-methoxy substituted acetamidostilbenes, by contrast, yielded the bisindoline dimer (36).
- Ahmad, Kartini,Thomas, Noel F.,Mukhtar, Mat Ropi,Noorbatcha, Ibrahim,Faizal Weber, Jean-Frederic,Nafiah, Mohd Azlan,Velu, Saraswati S.,Takeya, Koichi,Morita, Hiroshi,Lim, Chuan-Gee,Hadi, A. Hamid A.,Awang, Khalijah
-
experimental part
p. 1504 - 1516
(2009/05/07)
-
- Design and synthesis of 1-benzazepine derivatives by strategic utilization of Suzuki-Miyaura cross-coupling, aza-Claisen rearrangement and ring-closing metathesis
-
A new and simple methodology has been realized for the synthesis of 7-substituted 2,3,4,5-tetrahydro-1-benzazepine derivatives with Suzuki-Miyaura cross-coupling, aza-Claisen rearrangement and ring-closing metathesis (RCM) the key steps. Here, o-allylacet
- Kotha, Sambasivarao,Shah, Vrajesh R.
-
scheme or table
p. 1054 - 1064
(2009/04/05)
-
- An efficient and versatile one-pot Beckmann rearrangement of ketoximes using mesitylenesulfonyl chloride
-
A variety of oxime mesitylenesulfonates, generated in situ from their heterocyclic, carbocyclic, and acyclic ketoximes in the presence of lithium hydroxide in tetrahydrofuran, efficiently rearrange into their corresponding lactams and amides. The stereochemistry of diazepan-5-one lactams resulting from the rearrangement of heterocyclic ketoximes (piperidin-4-one oximes), has been deduced based on one- and two-dimensional NMR analyses. The seven-membered heterocyclic ring of the product lactams adopts chair conformations with equatorial configurations of all the alkyl and aryl substituents except one of the methyl groups at C-3 on a 3,3-disubstituted product, which possess an axial configuration. Georg Thieme Verlag Stuttgart.
- Ramalingan, Chennan,Park, Yong-Tae
-
p. 1351 - 1358
(2008/12/21)
-
- Iron-catalyzed aryl-aryl cross-coupling reaction tolerating amides and unprotected quinolinones
-
The iron(III)-catalyzed cross-coupling reaction between functionalized arylcopper reagents and aromatic iodides bearing an amide function or an unprotected quinolinone leads smoothly to polyfunctionalized biphenyls in excellent yields due to an intramolec
- Kofink, Christiane C.,Blank, Benoit,Pagano, Sandro,Goetz, Nadine,Knochel, Paul
-
p. 1954 - 1956
(2008/02/07)
-
- INDOLE DERIVATIVES AS HISTAMINE 3 RECEPTOR INHIBITORS FOR THE TREATMENT OF COGNITIVE AND SLEEP DISORDERS, OBESITY AND OTHER CNS DISORDERS
-
This invention relates to compounds having pharmacological activity, to compositions containing these compounds, and to a method of treatment employing the compounds and compositions. More particularly, this invention concerns certain indole derivatives and their salts and solvates. These compounds have H3 histamine receptor antagonist activity. This invention also relates to pharmaceutical compositions containing these compounds and to a method of treating disorders in which histamine H3 receptor blockade is beneficial.
- -
-
Page/Page column 36-37
(2008/06/13)
-
- Mercury-catalyzed rearrangement of ketoximes into amides and lactams in acetonitrile
-
(Chemical Equation Presented) An acetonitrile solution of mercury(II) chloride has been found to catalyze efficiently the conversion of a diverse range of ketoximes into their corresponding amides/lactams.
- Ramalingan, Chennan,Park, Yong-Tae
-
p. 4536 - 4538
(2008/02/04)
-
- A palladium-catalyzed tandem cyclization-cross-coupling reaction using indolylborate as a transfer agent
-
Investigation of the palladium-catalyzed tandem cyclization-cross-coupling reaction using indolylborate (2) as a transfer agent has been carried out. Furthermore, the cross-coupling reaction performed under carbon monoxide led to the generation of indolyl
- Ishikura, Minoru,Takahashi, Norinobu,Yamada, Koji,Yanada, Reiko
-
p. 11580 - 11591
(2007/10/03)
-
- Rhodium-catalyzed multicomponent-coupling reactions involving a carborhodation-cross-coupling sequence
-
(Chemical Equation Presented) A rhodium-catalyzed multicomponent-coupling reaction has been developed that involves a cross-coupling with organohalides as part of the reaction sequence. Through several experiments toward mechanistic investigations, it has
- Shintani, Ryo,Yamagami, Takafumi,Hayashi, Tamio
-
p. 4799 - 4801
(2007/10/03)
-
- Synthesis, structure, and chemoselective reactivity of N-(2-iodylphenyl) acylamides: Hypervalent iodine reagents bearing a pseudo-six-membered ring.scaffold
-
A pseudo-benziodoxazine structure with intramolecular secondary I...O bonding, as shown by X-ray analysis, is seen in a series of N-(2-iodylphenyl) acylamides prepared from 2-iodoaniline (see scheme). These compounds contain a six-membered pseudocyclic scaffold about an iodine(v) center and are able to oxidize either alcohols or sulfides, with the reactivity depending largely on the substitution pattern on the amide group adjacent to the iodyl moiety. (Chemical Equation Presented).
- Ladziata, Uladzimir,Koposov, Alexey Y.,Lo, Ka Y.,Willging, Jeff,Nemykin, Victor N.,Zhdankin, Viktor V.
-
p. 7127 - 7131
(2007/10/03)
-
- Intramolecular C-N bond addition of amides to alkynes using platinum catalyst
-
The intramolecular aminoacylation of alkynes using ortho-alkynylacetanilides proceeds in very high yields in the presence of PtCl2 catalyst. This reaction provides not only a useful procedure for synthesizing 2,3-disubstituted indoles at once from ortho-alkynylaniline derivatives, but also an interesting mechanistic aspect; the intramolecular C-N bond addition of amides to alkynes takes place readily in the presence of Pt(II) catalyst. Copyright
- Shimada, Tomohiro,Nakamura, Itaru,Yamamoto, Yoshinori
-
p. 10546 - 10547
(2007/10/03)
-
- Hydrogen Bond-Stabilized Helix Formation of a m-Phenylene Ethynylene Oligomer
-
(Matrix Presented) Incorporation of a single hydrogen bonded β-turn mimic in the backbone of a m-phenylene ethynylene oligomer is shown to affect the thermodynamic properties of the folding reaction. Oligomers 1 and 2 both undergo solvophobic helix formation, but hydrogen bonded oligomer 1 was found to form a more stable helix with a higher tolerance to solvent denaturation than isomeric, non-hydrogen bonded oligomer 2.
- Cary, Jennifer M.,Moore, Jeffrey S.
-
p. 4663 - 4666
(2007/10/03)
-
- Sonogashira coupling and cyclization reactions on alumina: A route to aryl alkynes, 2-substituted-benzo[b]furans and 2-substituted-indoles
-
A solventless, microwave-enhanced Sonogashira coupling reaction of aromatic iodides with terminal alkynes on potassium fluoride doped alumina in the presence of palladium powder, cuprous iodide, and triphenylphosphine has been developed. The reaction can be utilized to prepare aryl alkynes in excellent yields. The coupling of o-iodophenol with terminal alkynes leads to the formation 2-substituted-benzo[b]furans. Whereas the coupling of o-iodoanilines with terminal alkynes generates indole products. An in situ desilylation reaction was also developed.
- Kabalka, George W.,Wang, Lei,Pagni, Richard M.
-
p. 8017 - 8028
(2007/10/03)
-
- Kinetics of aromatic iodination reactions using iodine, diiodine pentoxide and sulfuric acid in acetic acid
-
Kinetic studies of an aromatic iodination reaction using benzene or acetanilide, iodine, diiodine pentoxide and sulfuric acid in glacial acetic acid have been carried out. The reaction, followed using FT-Raman spectroscopy to monitor the disappearance of the aromatic over time, exhibits fractional order dependence in benzene but first order dependence in acetanilide. The difference in order between the two aromatics indicates that benzene participates in an equilibrium reaction before the rate limiting step of the reaction. This reversible step is proposed to be the reversible formation of a π-complex between adsorbed I2 and benzene as it adsorbs onto I2O5. Based on the calculated order, acetanilide most likely does not form a π-complex with adsorbed I2, rather it reacts from solution to form a σ-complex with activated I2 on the I2O5 surface. In both reactions, it is proposed that the rate limiting step is the formation of the σ-complex.
- Brazdil, Linda C.,Fitch, Jill L.,Cutler, Carlo J.,Haynik, Denise M.,Ace, Eryn R.
-
p. 933 - 936
(2007/10/03)
-