- Improved protocols for molybdenum- und tungsten-catalyzed hydrostannations
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A series of (isonitrile)tungsten carbonyl complexes of type W(CO) m(CNR)n has been synthesized and evaluated as hydrostannation catalysts. The results are compared with those obtained by the previously reported tri(tert-butylisonitri
- Wesquet, Alexander O.,Kazmaier, Uli
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Read Online
- Parameters affecting the microwave-specific acceleration of a chemical reaction
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Under appropriate conditions, significant microwave-specific enhancement of the reaction rate of an organic chemical reaction can be observed. Specifically, the unimolecular Claisen rearrangement of allyl p-nitrophenyl ether (ApNE) dissolved in naphthalen
- Chen, Po-Kai,Rosana, Michael R.,Dudley, Gregory B.,Stiegman
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Read Online
- Palladium-Catalyzed Double-Decarboxylative Addition to Pyrones: Synthesis of Conjugated Dienoic Esters
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An interceptive decarboxylative allylation protocol has been developed utilizing pyrone as a C4 synthon. This palladium-catalyzed transformation difunctionalizes the pyrone moiety by in situ generation and activation of both the electrophile and nucleophi
- Maji, Tapan,Tunge, Jon A.
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Read Online
- Determination on temperature gradient of different polar reactants in reaction mixture under microwave irradiation with molecular probe
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Temperature accurate measurement is one of key issues in illustration of the rate increase in the microwave-promoted organic reactions because reaction rates are closely related with reaction temperature. The use of molecular probe is reported as a tool to identify the microwave selective heating effects in homogenous reaction mixture of intramolecular aromatic Claisen rearrangement. Our results show direct evidence for localized superheating of polar reactants in nonpolar solvent. While in the polar solvent, the microwave selective heating effects of polar reactants will be decreased.
- Li, Xinhao,Xu, Jiaxi
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Read Online
- Pyrene-Tagged Alcoholic Ionic Liquids as Phase Transfer Catalysts for Nucleophilic Fluorination
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Functional group?activity relationships of pyrene-tagged ionic liquid (PTIL)-based organocatalysts for nucleophilic fluorination using alkali metal fluorides (MFs) are described, which demonstrate that the pyrene, oligoether and alcohol moieties on the imidazolium ring are vital for efficient catalysis. Further investigation of these findings led to the discovery of new strategy, which showed superior catalyst separation process, i.e., catalyst is effortlessly separated from the reaction mixture using reduced graphene oxide. The catalytic efficiency of the PTIL as a phase transfer catalyst was demonstrated by the high conversion of the reactants up to 98% fluorinated yield using MFs in CH3CN or t-amyl alcohol. Importantly, the catalyst not only enhanced the reactivity of bimolecular nucleophilic substitutions (SN2) within a short reaction time and reduces the formation of by-products but also affords high yield with easy isolation and separation under mild conditions.
- Taher, Abu,Kim, Dong Wook
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Read Online
- Light-Promoted C–N Coupling of Aryl Halides with Nitroarenes
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A photochemical C–N coupling of aryl halides with nitroarenes is demonstrated for the first time. Catalyzed by a NiII complex in the absence of any external photosensitizer, readily available nitroarenes undergo coupling with a variety of aryl halides, providing a step-economic extension to the widely used Buchwald–Hartwig C–N coupling reaction. The method tolerates coupling partners with steric-congestion and functional groups sensitive to bases and nucleophiles. Mechanistic studies suggest that the reaction proceeds via the addition of an aryl radical, generated from a NiI/NiIII cycle, to a nitrosoarene intermediate.
- Li, Gang,Yang, Liu,Liu, Jian-Jun,Zhang, Wei,Cao, Rui,Wang, Chao,Zhang, Zunting,Xiao, Jianliang,Xue, Dong
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supporting information
p. 5230 - 5234
(2021/02/05)
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- Aluminium chloride-potassium iodide-acetonitrile system: A mild reagent system for aromatic claisen rearrangement at ambient temperature
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Claisen rearrangement is used as the standard methods for the generation of complex organic substance. It is one of the well-known methods for the introduction of carbon-carbon bond. We have developed a protocol using allyl aryl ether as a substrate and AlCl3-KI as a mild reagent system and acetonitrile (CH3CN) is taken as solvent at ambient temperature. The reagent system presented in this current work is found to be appropriate for Claisen rearrangement of several aromatic alcohols with excellent yields.
- Bhattacharyya, Nayan Kamal,Dutta, Deepjyoti,Biswas, Joydeep
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- Allylphenols as a new class of human 15-lipoxygenase-1 inhibitors
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In this study, a series of mono- and diallylphenol derivative were designed, synthesized, and evaluated as potential human 15-lipoxygenase-1 (15-hLOX-1) inhibitors. Radical scavenging potency of the synthetic allylphenol derivatives was assessed and the results were in accordance with lipoxygenase (LOX) inhibition potency. It was found that the electronic natures of allyl moiety and para substituents play the main role in radical scavenging activity and subsequently LOX inhibition potency of the synthetic inhibitors. Among the synthetic compounds, 2,6-diallyl-4-(hexyloxy)phenol (42) and 2,6-diallyl-4-aminophenol (47) showed the best results for LOX inhibition (IC50 = 0.88 and 0.80 μM, respectively).
- Alavi, Seyed Jamal,Seyedi, Seyed Mohammad,Saberi, Satar,Safdari, Hadi,Eshghi, Hossein,Sadeghian, Hamid
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p. 259 - 266
(2020/10/12)
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- Aryl Ether Syntheses via Aromatic Substitution Proceeding under Mild Conditions
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In this study, mild conditions for aromatic substitutions during the syntheses of aryl ethers were developed. In the reaction conditions, the choices of solvent, base, and the sequence for the addition of the reagents proved important. A wide variety of alcohols were used directly as nucleophiles and smoothly reacted with aryl chlorides that possessed either a nitro or a cyano group at either the ortho- or para-position. Controlled experiments we performed suggested that the reaction underwent a charge-transfer process mediated by a combination of DMF and tert-BuOK.
- Ando, Shin,Tsuzaki, Marina,Ishizuka, Tadao
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p. 11181 - 11189
(2020/10/12)
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- Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates
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The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.
- Hui, Zi,Jiang, Songwei,Qi, Xiang,Ye, Xiang-Yang,Xie, Tian
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supporting information
(2020/05/18)
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- Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis
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The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.
- Daniliuc, Constantin G.,Gilmour, Ryan,Neufeld, Jessica,Sarie, Jér?me C.,Thiehoff, Christian
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supporting information
p. 15069 - 15075
(2020/06/17)
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- Chemoselective Epoxidation of Allyloxybenzene by Hydrogen Peroxide Over MFI-Type Titanosilicate
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The chemoselective synthesis of 2-(phenoxymethyl)oxirane from allyloxybenzene is achieved with over 90 % yield in a sustainable reaction system using titanium-substituted silicalite-1 (TS-1) as a catalyst, hydrogen peroxide (H2O2) as an oxidant, and a mixture of MeOH/MeCN as a solvent at 40 °C. No acid-catalyzed side reactions prompted by the Lewis acidity of the Ti active site in TS-1 are observed. The TS-1 catalyst can also promote the formation of oxiranes from various p-substituted allyloxybenzenes in good yields. The reaction mechanism is investigated through the reaction with other allyloxy compounds. The results, which are supported by DFT calculations, indicate that an active species of Ti peroxides formed from the reaction of TS-1 with H2O2 selectively oxidizes the allyloxybenzene to 2-(phenoxymethyl)oxirane.
- Fujitani, Tadahiro,Hong, Dachao,Ito, Satoru,Ji, Xinyi,Kon, Yoshihiro,Nakashima, Takuya,Osuga, Ryota,Sato, Kazuhiko,Yokoi, Toshiyuki
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supporting information
(2020/04/15)
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- NOVEL MACROCYCLIC DERIVATIVES, PROCESS FOR PREPARING SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
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Compound of formula (I): wherein A1, A2, Ra, Rb, Rc, Rd, R3, R4, X, Y and G are as defined in the description, and their use in the manufacture of medicaments.
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Paragraph 0452-0454
(2020/08/25)
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- Catalytic reduction of aryl trialkylammonium salts to aryl silanes and arenes
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A new approach for the reduction of aryl ammonium salts to arenes or aryl silanes using nickel catalysis is reported. This method displays excellent ligand-controlled selectivity based on the N-heterocyclic carbene (NHC) ligand employed. Utilizing a large NHC in non-polar solvents generates aryl silanes, while small NHCs in polar solvents promote reduction to arenes. Several classes of aryl silanes can be accessed from simple aniline building blocks, including those useful for cross-couplings, oxidations, and halogenations. The reaction conditions are mild, functional group tolerant, and provide efficient access to a variety of benzene derivatives.
- Rand, Alexander W.,Montgomery, John
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p. 5338 - 5344
(2019/05/29)
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- Synthesis of Benzofuran and Indole Derivatives Catalyzed by Palladium on Carbon
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Benzofurans and indoles are key moieties in many natural products and pharmaceuticals. Herein, we describe a cheap and easy-to-execute strategy for the synthesis of benzofurans and indoles, employing Pd/C as the promoter. A variety of substituted allyl-anilines and allyl-phenols were converted into the desired products in good to excellent yields. Recycling of Pd/C was possible up to five cycles, keeping similar levels of reactivity.
- Savvidou, Anatoli,IoannisTzaras, Dimitrios,Koutoulogenis, Giorgos S.,Theodorou, Alexis,Kokotos, Christoforos G.
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supporting information
p. 3890 - 3897
(2019/06/27)
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- Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement
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A tandem relay catalytic protocol using both Pd and isothiourea catalysis has been developed for the enantioselective synthesis of α-amino acid derivatives containing two stereogenic centers from readily accessible N,N-disubstituted glycine aryl esters and allylic phosphates. The optimized process uses a bench-stable succinimide-based Pd precatalyst (FurCat) to promote Pd-catalyzed allylic ammonium salt generation from the allylic phosphate and the glycine aryl ester. Subsequent in situ enantioselective [2,3]-sigmatropic rearrangement catalyzed by the isothiourea benzotetramisole forms syn-α-amino acid derivatives with high diastereo- and enantioselectivity. This methodology is most effective using 4-nitrophenylglycine esters and tolerates a variety of substituted cinnamic and styrenyl allylic ethyl phosphates. The use of challenging unsymmetrical N-allyl-N-methylglycine esters is also tolerated under the catalytic relay conditions without compromising stereoselectivity.
- Spoehrle, Stéphanie S. M.,West, Thomas H.,Taylor, James E.,Slawin, Alexandra M. Z.,Smith, Andrew D.
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supporting information
p. 11895 - 11902
(2017/09/07)
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- Synthesis of Selectively Substituted or Deuterated Indenes via Sequential Pd and Ru Catalysis
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A strategy for the synthesis of functionalized indenes is presented. The readily available substituted phenols are used as starting materials in the reaction sequence composed of Pd-catalyzed Suzuki coupling and Ru-catalyzed ring-closing metathesis, thus representing a practical method for the controlled construction of functionalized indene derivatives. The methodology has been successfully applied to a broad range of substrates, producing substituted indenes in excellent yields. This approach is also utilized for the synthesis of substituted indenes selectively deuterated in position 3, which are rare in literature.
- Jana, Anupam,Misztal, Kasjan,Zak, Anna,Grela, Karol
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p. 4226 - 4234
(2017/04/28)
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- Facile one-pot synthesis of aliphatic bridged diaryloxy compounds, cyclic and crown ethers under mild conditions
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We report here the facile, room temperature, catalyst free, one pot synthesis of aliphatic bridged diaryloxy compounds, cyclic and crown ethers. Anhydrous potassium carbonate (K2CO3) as a mild base along with dimethyl sulfoxide gener
- Sakate, Sachin,Kamble, Sumit,Chikate, Rajiv,Rode, Chandrashekhar
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p. 462 - 470
(2017/03/27)
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- Palladium-Catalyzed Fluoroalkylative Cyclization of Olefins
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A palladium-catalyzed fluoroalkylative cyclization of olefins with readily available Rf-I reagents to afford the corresponding fluoroalkylated 2,3-dihydrobenzofuran and indolin derivatives with moderate to excellent yields is reported. This novel procedure provides an efficient method for the construction of Csp3-CF2 and C-O/N bonds in one step. A wide range of functional groups are tolerated. It is proposed that a radical/SET (single electron transfer) pathway proceeding via the fluoroalkyl radical may be involved in the catalytic cycle.
- Liao, Jianhua,Fan, Lianfeng,Guo, Wei,Zhang, Zhenming,Li, Jiawei,Zhu, Chuanle,Ren, Yanwei,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 1008 - 1011
(2017/03/15)
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- Green Organocatalytic Synthesis of Dihydrobenzofurans by Oxidation-Cyclization of Allylphenols
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A green and cheap protocol for the synthesis of dihydrobenzofurans via an organocatalytic oxidation of o -allylphenols is presented. The use of 2,2,2-trifluoroacetophenone and H 2 O 2 as the oxidation system, leads to a highly useful synthetic method, where a variety of substituted o -allylphenols were cyclized in high yields..
- Triandafillidi, Ierasia,Sideri, Ioanna K.,Tzaras, Dimitrios Ioannis,Spiliopoulou, Nikoleta,Kokotos, Christoforos G.
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supporting information
p. 4254 - 4260
(2017/09/12)
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- Multicomponent, fragment-based synthesis of polyphenol-containing peptidomimetics and their inhibiting activity on beta-amyloid oligomerization
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A new and short fragment-based approach towards artificial (but "natural-based") complex polyphenols has been developed, exploiting the Ugi multicomponent reaction of phenol-containing simple substrates. The resulting library of compounds has been tested
- Lambruschini, Chiara,Galante, Denise,Moni, Lisa,Ferraro, Francesco,Gancia, Giulio,Riva, Renata,Traverso, Alessia,Banfi, Luca,D'Arrigo, Cristina
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p. 9331 - 9351
(2017/11/22)
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- Oxidative cyclization of alkenoic acids promoted by AgOAc
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Alkenoic acids derived from salicylic acid and analogues undergo an unexpected oxidative cyclization process triggered by AgOAc leading to 4H-benzo[d][1,3]dioxin-4-ones. The process is affected by the substitution on the aryl and the allyl units.
- Carrillo-Arcos, Ulises A.,Rojas-Ocampo, Jonathan,Porcel, Susana
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supporting information
p. 479 - 483
(2016/01/09)
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- In situ production of silver nanoparticles on an aldehyde-equipped conjugated porous polymer and subsequent heterogeneous reduction of aromatic nitro groups at room temperature
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In a metal-free procedure, chelating thiol groups and an electrophile react to assemble a robust, conjugated porous polymer with pendant aldehyde functionalities. These groups are able to reduce Ag(I) ions to generate, in situ, Ag(0) nanoparticles evenly dispersed in the polymer matrix. The Ag(0)-polymer composite enables selective reduction of aromatic nitro compounds as a heterogeneous catalyst, and can be conveniently recycled multiple times.
- Liu, Jie,Cui, Jieshun,Vilela, Filipe,He, Jun,Zeller, Matthias,Hunter, Allen D.,Xu, Zhengtao
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supporting information
p. 12197 - 12200
(2015/07/27)
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- Investigation on Claisen rearrangement of allyl phenyl ethers in near-critical water
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Catalyst-free Clasien rearrangement of allyl phenyl ethers were investigated in near-critical water. The effects on the reaction in near-critical water and conventional conditions were compared. The results demonstrate that near-critical water could greatly accelerate the Claisen rearrangement of allyl phenyl ethers. This process is simple, fast, efficient and environmentally benign.
- Xiao, Shangyou,He, Yi,Xu, Guang,Liu, Qi
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p. 3299 - 3305
(2015/06/08)
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- An efficient palladium-catalyzed synthesis of cinnamyl ethers from aromatic halides, phenols, and allylic chloride
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A one-pot, two-step catalytic protocol for the preparation of cinnamyl ethers from simple and readily available aryl halides, phenols and allyl chloride is reported for the first time. This simple and highly efficient palladium nanoparticles catalytic system shows good regio- and stereoselectivities and affords the desired products in good to high yields (49-85%) from aryl iodides. Furthermore, less reactive aryl bromides can also give the cinnamyl ethers in moderate yields (24-72%).
- Wang, Wei,Zhou, Rong,Jiang, Zhi-Jie,Wang, Kun,Fu, Hai-Yan,Zheng, Xue-Li,Chen, Hua,Li, Rui-Xiang
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supporting information
p. 616 - 622
(2014/05/20)
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- Room temperature, metal-free arylation of aliphatic alcohols
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Diaryliodonium salts are demonstrated as efficient arylating agents of aliphatic alcohols under metal-free conditions. The reaction proceeds at room temperature within 90 min to give alkyl aryl ethers in good to excellent yields. Aryl groups with electron
- Ghosh, Raju,Lindstedt, Erik,Jalalian, Nazli,Olofsson, Berit
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- A rare case of facial selectivity inversion for Sharpless asymmetric dihydroxylation in a series of structurally homogeneous substrates: Synthesis of non-racemic 3-(nitrophenoxy)-propane-1,2-diols
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Asymmetric dihydroxylation of mono nitrophenyl allyl ethers leads to the corresponding non-racemic 3-(nitrophenoxy)-propane-1,2-diols 1a-c. As this takes place, regardless of the reagent used (AD-mix-α or AD-mix-β), the configuration of the predominant enantiomer for the para- and meta-nitrosubstituted products is opposite to the configuration of the ortho-nitrophenyl derivative. A correlation between the melting points and vibrational spectra of the racemic and enantiopure diols 1a-c allowed us to establish that all of the chiral substances investigated formed stable racemic compounds in the solid phase.
- Bredikhina, Zemfira A.,Kurenkov, Alexey V.,Antonovich, Olga A.,Pashagin, Alexander V.,Bredikhin, Alexander A.
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p. 1015 - 1021
(2014/08/18)
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- Metal-free synthesis of aryl ethers in water
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The first arylation of allylic and benzylic alcohols with diaryliodonium salts is reported. The reaction yields alkyl aryl ethers under mild and metal-free conditions. Phenols are arylated to diaryl ethers in good to excellent yields. The reaction employs diaryliodonium salts and sodium hydroxide in water at low temperature, and excess amounts of the coupling partners are avoided.
- Lindstedt, Erik,Ghosh, Raju,Olofsson, Berit
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supporting information
p. 6070 - 6073
(2014/01/06)
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- Efficient allylation of nucleophiles catalyzed by a bifunctional heterogeneous palladium complex-tertiary amine system
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We demonstrate the synergistic catalysis of a silica-supported diaminopalladium complex and a tertiary amine (SiO2/diamine/Pd/ NEt2) as well as synthetic scope of the Tsuji-Trost reaction of 1,3-dicarbonyls, phenols, and carboxylic acids with allyl carbonate and acetates. The synergistic catalysis of SiO2/diamine/Pd/NEt 2 exhibited wide applicability and high activity for the Tsuji-Trost reaction. For example, the reaction of ethyl 3-oxobutanate with allyl methyl carbonate afforded the allylated product in >99% yield at 70 °C for 5 h. The yield of allylated products was 26% for SiO2/diamine/Pd, without immobilization of the tertiary amine group. In the reaction of 1.0 mmol of ethyl 3-oxobutanate using 0.60 μmol of Pd in SiO2/diamine/Pd/NEt 2, the turnover number (TON) of Pd reached up to 1070 within 24 h. Phenols with electron-withdrawing groups, such as nitro and chloro groups, on the para position resulted in high product yields. The SiO2/diamine/ Pd/NEt2 catalyst was reusable at least 4 times without appreciable loss of its activity and selectivity in the reaction of p-chlorophenol. Copyright
- Noda, Hiroto,Motokura, Ken,Miyaji, Akimitsu,Baba, Toshihide
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p. 973 - 980
(2013/05/08)
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- Synthesis and SAR studies of 3-allyl-4-prenyloxyaniline amides as potent 15-lipoxygenase inhibitors
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15-Lipoxygenases are one of the nonheme iron-containing proteins with ability of unsaturated lipid peroxidation in animals and plants. The critical role of the enzymes in formation of inflammations, sensitivities and some of cancers has been demonstrated in mammalians. Importance of the 15-lipoxygenases leads to development of mechanistic studies, products analysis and synthesis of their inhibitors. In this work new series of the 3-allyl-4-allyoxyaniline amides and 3-allyl-4-prenyloxyaniline amides were designed, synthesized and their inhibitory potency against soybean 15-lipoxygenase were determined. Among the synthetic amides, 3-allyl-4-(farnesyloxy)-adamantanilide showed the most potent inhibitory activity by IC50 value of 0.69 μM. SAR studies showed that in spite of prenyl length increases, the effects of the amide size and its electronic properties on the inhibitory potency became predominant. The SAR studies was also showed that the orientation of allyl and prenyloxy moieties toward Fe core of the SLO active site pocket is the most suitable location for enzyme inhibition.
- Jabbari, Atena,Davoodnejad, Mahdieh,Alimardani, Maliheh,Assadieskandar, Amir,Sadeghian, Ali,Safdari, Hadi,Movaffagh, Jebraeel,Sadeghian, Hamid
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p. 5518 - 5526
(2012/10/30)
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- TBAF-promoted elimination of vicinal dibromides having an adjacent O-functional group: Syntheses of 2-bromoalk-1-enes and alkynes
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Syntheses of 2-bromoalk-1-enes and alkynes were achieved in good yields by dehydrobromination of vicinal dibromides with tetrabutylammonium fluoride. Neighboring O-functional-group participation is important in determining elimination reactivity. Georg Thieme Verlag Stuttgart New York.
- Kutsumura, Noriki,Kubokawa, Keisuke,Saito, Takao
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experimental part
p. 2377 - 2382
(2011/09/16)
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- Synthesis of alkyl-aryl ethers by copper-catalyzed etherization reactions of aryl fluorides with tetraalkylammonium bromides and H2O
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Synthesis of alkyl aryl ethers via copper-catalyzed etherizations of electron-deficient aryl fluorides with quaternary ammonium bromides and water has been developed. In the presence of Cu(OAc)2, POPh3 (L4) and Cs2CO3, a variety of electron-deficient aryl fluorides underwent the reaction with quaternary ammonium bromides and H 2O in moderate to good yields. The mechanism was also discussed. Synthesis of alkyl aryl ethers via copper-catalyzed etherizations of electron-deficient aryl fluorides with quaternary ammonium bromides and water has been developed. In the presence of Cu(OAc)2, POPh3 (L4) and Cs2CO3, a variety of electron-deficient aryl fluorides underwent the reaction with quaternary ammonium bromides and H 2O in moderate to good yields. Copyright
- Wang, Feng,Tang, Boxiao,Xie, Yexiang,Li, Jinheng
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experimental part
p. 2318 - 2322
(2011/10/03)
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- Fused ring compound and use thereof
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The present invention provides a compound represented by the formula: wherein the symbols are as described in the specification, or a salt thereof, which is useful for preventing/treating eicosanoid-associated diseases such as atherosclerosis, diabetes, obesity, atherothrombosis, asthma, fever, pain, cancer, rheumatism, osteoarthritis and atopic dermatitis, and which has an excellent pharmacological action, physicochemical properties, etc.
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Page/Page column 39
(2010/08/07)
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- Design, synthesis and SAR studies of 4-allyoxyaniline amides as potent 15-lipoxygensae inhibitors
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A group of 4-allyloxyaniline amides 5a-o were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compound 5e showed the best IC50 in SLO inhibition (IC50 = 0.67 ± 0.06 μM). All compounds were docked in SLO active site retrieved from RCSB Protein Data Bank (PDB entry: 1IK3) and showed that allyloxy group of compounds is oriented towards the Fe3+-OH moiety in the active site of enzyme and fixed by hydrogen bonding with two conserved His513 and Gln716. It is resulted that molecular volume of the amide moiety would be a major factor in inhibitory potency variation of the synthetic amides, where the hydrogen bonding of the amide group could also involve in the activity of the inhibitors.
- Seyedi, Seyed Mohammad,Jafari, Zeinab,Attaran, Neda,Sadeghian, Hamid,Saberi, Mohammad Reza,Riazi, Mohammad Mahdi
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experimental part
p. 1614 - 1622
(2009/08/15)
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- N-heterocyclic carbene-catalyzed enantioselective mannich reactions with α-aryloxyacetaldehydes
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(Chemical Equation Presented) N-Heterocyclic carbenes (NHCs) catalyze a new Mannich-type reaction to form β-amino acid derivatives in high yield and enantioselectivity. The reaction is initiated by the addition of an NHC to an C-aryloxyaldehyde followed by elimination of a phenoxide anion which generates an enol/enolate. A Mannich addition to a tosylimine proceeds with excellent control over enantioselectivity. In a new carbene catalysis concept, catalyst regeneration is promoted by return, or rebound, and acylation of the phenoxide group which served as the activating component in the first step of the catalytic cycle. The activated ester products formed in situ are manipulated to form a variety of useful compounds including β-amino acids, β-amino amides, and peptides.
- Kawanaka, Yasufumi,Phillips, Eric M.,Scheidt, Karl A.
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supporting information; experimental part
p. 18028 - 18029
(2010/03/26)
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- BICYCLOSULFONYL ACID (BCSA) COMPOUNDS AND THEIR USE AS THERAPEUTIC AGENTS
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This invention pertains generally to the field of therapeutic compounds, and more particularly, to certain bicyclosulfonyl acid (BCSA) compounds which act as inhibitors of Tumour Necrosis Factor-α Converting Enzyme (TACE). The compounds are useful in the
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Page/Page column 67; 85-86
(2009/01/20)
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- An efficient intermolecular BINAM-copper(I) catalyzed Ullmann-type coupling of aryl iodides/bromides with aliphatic alcohols
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A wide range of alkyl aryl ethers are synthesized from the corresponding aryl iodides and aliphatic alcohols through Ullmann-type intermolecular coupling reactions in the presence of a catalytic amount of easily available BINAM-CuI complex. Less reactive aryl bromides have also been shown to react with aliphatic alcohols under identical reaction conditions to give good yields of the alkyl aryl ethers without increasing the reaction temperature and time.
- Naidu, Ajay B.,Sekar
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p. 3147 - 3151
(2008/09/20)
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- Montmorillonite-entrapped sub-nanoordered Pd clusters as a heterogeneous catalyst for allylic substitution reactions
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(Chemical Equation Presented) Caught making a change: Stable sub-nanoordered Pd clusters within the interlayer spaces of montmorillonite efficiently catalyze heterogeneous allylic substitution reactions in which the coordinatively unsaturated Pd atoms enable facile formation of π-allylpalladium intermediates (see scheme). The catalyst is reusable without any loss of activity or selectivity.
- Mitsudome, Takato,Nose, Kenta,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Jitsukawa, Koichiro,Kaneda, Kiyotomi
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p. 3288 - 3290
(2008/03/11)
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- Surfactant-mediated solvent-free dealkylative cleavage of ethers and esters and trans-alkylation under neutral conditions
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A simple, surfactant-mediated, one-pot, solvent-free dealkylative cleavage of aryl ethers and esters followed by subsequent optional trans-alkylation under essentially neutral conditions has been developed.
- Bhattacharya, Apurba,Patel, Nitin C.,Vasques, Tomas,Tichkule, Ritesh,Parmar, Gaurang,Wu, Jiejun
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p. 565 - 567
(2007/10/03)
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- Palladium Nanoparticles in Polymers: Catalyst for Alkene Hydrogenation, Carbon-Carbon Cross-Coupling Reactions, and Aerobic Alcohol Oxidation
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A new recyclable palladium catalyst was synthesized by a simple procedure from readily available reagents, which is composed of palladium nanoparticles dispersed in an organic polymer. This catalyst is robust, and highly active in many organic transformations including alkene and alkyne hydrogenation, carbon-carbon cross-coupling reactions, and aerobic alcohol oxidation.
- Park, Cheon Min,Kwon, Min Serk,Park, Jaiwook
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p. 3790 - 3794
(2008/02/09)
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- An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans
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Twelve substituted benzofurans were synthesized from their corresponding substituted 1-allyl-2-allyloxybenzenes using ruthenium-mediated C- and O-allyl isomerization followed by ring-closing metathesis.
- Van Otterlo, Willem A.L.,Morgans, Garreth L.,Madeley, Lee G.,Kuzvidza, Samuel,Moleele, Simon S.,Thornton, Natalie,De Koning, Charles B.
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p. 7746 - 7755
(2007/10/03)
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- Ring-closing metathesis for the synthesis of 2H- and 4H-chromenes
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Six 4H-chromenes were synthesized from substituted phenols using vinylstannylation and ring-closing metathesis (RCM) as key steps. In addition, a different approach involving amongst other steps, an aryl allyl isomerization and RCM afforded a set of seven 2H-chromenes from phenolic precursors.
- Van Otterlo, Willem A.L.,Ngidi, E. Lindani,Kuzvidza, Samuel,Morgans, Garreth L.,Moleele, Simon S.,De Koning, Charles B.
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p. 9996 - 10006
(2007/10/03)
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- Compound having silsesquioxane skeleton and its polymer
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The present invention relates to a compound represented by Formula (1) and a polymer obtained using the compound: wherein R1 is phenyl which may have substituents, Q1 is hydrogen, halogen, alkyl having 1 to 10 carbon atoms, cycloprop
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- CYCLIC GUANIDINES, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF USE
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The present invention relates to cyclic guanidines, compositions containing such compounds and methods of treatment. The compounds are glucagon receptor antagonists and thus are useful for treating, preventing or delaying the onset of type 2 diabetes mellitus.
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Page/Page column 68
(2010/02/12)
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- Ortho- and para-substituted Hoveyda-Grubbs carbenes. An improved synthesis of highly efficient metathesis initiators
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A novel highly efficient and general route to various 3- and 5-substituted 2-alkoxystyrenes, required for the preparation of Hoveyda-Grubbs catalysts, is described.
- Bujok, Robert,Bieniek, Michal,Masnyk, Marek,Michrowska, Anna,Sarosiek, Agata,Stepowska, Halszka,Arlt, Dieter,Grela, Karol
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p. 6894 - 6896
(2007/10/03)
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- Addition of nitrile oxides to aryl allyl ethers
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3,5-Disubstituted isoxazolines with an aryloxymethyl group in position 5 have been synthesized. The [2+3] cycloaddition reaction of benzonitrile oxide to a 5-chlorosalicylic acid derivative containing two allyl groups occurs to give a compound with an oxa
- Alksnis,Muravenko,Dirnens,Lukevics
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p. 797 - 800
(2007/10/03)
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- The polymer incarcerated method for the preparation of highly active heterogeneous palladium catalysts
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A new method named "the polymer incarcerated (PI) method" for preparing a heterogeneous palladium catalyst has been developed. The method is operationally simple, and the Pd catalyst prepared (PI Pd) is highly active for hydrogenation, carbon-carbon, and carbon-oxygen bond-forming reactions. Remarkable points are that the activity of PI Pd is higher than that of homogeneous Pd catalysts and that PI Pd is recovered by simple filtration and reused several times without loss of activity. The catalyst is expected to replace many heterogeneous palladium catalysts, especially Pd/C, which is often used in academia and industry, but recovery of which is difficult. Copyright
- Akiyama, Ryo,Kobayashi, Shu
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p. 3412 - 3413
(2007/10/03)
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- Positive allosteric modulators of the nicotinic acetylcholine receptor
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The invention provides compounds of Formula I: These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful in pharmaceuticals used to treat diseases or conditions in which α7 nAChR is known to be involved.
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- Pentafluorobenzenesulfonamides and analogs
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The invention provides methods and compositions relating to novel pentafluorophenylsulfonamide derivatives and analogs and their use as pharmacologically active agents. The compositions find particular use as pharmacological agents in the treatment of disease states, particularly cancer, vascular restenosis, microbial infections, and psoriasis, or as lead compounds for the development of such agents. The compositions include compounds of the general formula I:
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- Transformation of terminal diols of cyclic and acyclic saccharides to epoxides and alkenes by reaction with triphenylphosphine, imidazole and iodine
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Reaction of various terminal diols 1,4,6,8-12, derived from cyclic and acyclic monosaccharides, with 2 mol equivalents each of TPP-imidazole-I2 between -8 °C and 15 °C in THF afforded the corresponding epoxides 2,5,7,13-17, respectively, with 4
- Mereyala, Hari Babu,Goud, P. Mallikarjun,Gadikota, Rajendrakumar Reddy,Reddy, K. Ramasubba
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p. 1211 - 1222
(2007/10/03)
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