- An economical and safe procedure to synthesize 2-hydroxy-4-pentynoic acid: A precursor towards 'clickable' biodegradable polylactide
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2-Hydroxy-4-pentynoic acid (1) is a key intermediate towards 'clickable' polylactide which allows for efficient introduction of a broad range of pendant functional groups onto polymers from a single monomer via convenient 'click' chemistry with organic az
- Zhang, Quanxuan,Ren, Hong,Baker, Gregory L.
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Read Online
- A chemical labeling of N6-formyl adenosine (f6A) RNA
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N6-methyl adenosine (m6A) is an eminent epigenetic mark in mRNAs that affects a broad range of biological functions in diverse species. However, the chemically inert methyl group prevents a direct labeling of this modification for subsequent detection and sequencing. Therefore, most current approaches for the labeling of m6A still have limitations of relying on the utilization of corresponding methyltransferases, which resulted in the lacking of efficiency. Here we present an approach which selectively alkylated the N6-formyl adenosine (f6A), the key intermediate during chemical oxidation of m6A, with an alkyne functionality that can be further labeled with click reactions. This covalent labeling approach will be able to facilitate in the affinity purification, detection and genome-wide profiling studies.
- Cheng, Liang,Lin, Cui-Lian,Liu, Li,Xie, Li-jun
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supporting information
(2021/10/06)
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- Green one-pot four-component synthesis of 3,5-disubstituted isoxazoles- sulfonates and sulfonamides using a combination of NaDCC as metal-free catalyst and ultrasonic activation in water
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A simple and green one-pot reaction has been proposed for the synthesis of novel 3,5-disubstituted isoxazole-sulfonates and -sulfonamides (5a-j) in water under ultrasound irradiation. The methodology is based on the use of safe and environmentally friendly reagents and allows, via in-situ 1,3-dipolar cycloaddition, an easy access to functionalized heterocycles with the creation of four new bonds (S[sbnd]O, C[sbnd]N, C[sbnd]O and C[sbnd]C). Comparison studies using classical magnetic stirring and ultrasound irradiation clearly showed that sonication promoted clean transformation, high yields (72–89%) and faster reactions (20–28 min). All the synthesized compounds were fully characterized by MS-ES, 1H NMR, 13C NMR spectroscopy and HPLC analysis.
- Talha, Aicha,Tachallait, Hamza,Benhida, Rachid,Bougrin, Khalid
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supporting information
(2021/09/13)
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- Synthesis of fish scale derived hydroxyapatite silica propyl bis aminoethoxy ethane cuprous complex (HASPBAEECC) as a novel hybrid nano-catalyst for highly efficient synthesis of new benzimidazole-1,2,3-triazole hybrid analogues as antifungal agents
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Abstract: The preparation, characterization and application of hydroxyapatite silica propyl bis aminoethoxy ethane cuprous complex (HASPBAEECC) as a novel hybrid nano-catalyst for synthesis of new benzimidazole-1,2,3-triazole hybrid analogues as promising
- Behrouz, Somayeh,Mohammad-Javadi, Mehdi,Soltani Rad, Mohammad Navid,Zarenezhad, Elham
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- Design and Synthesis of Oleanolic Acid Trimers to Enhance Inhibition of Influenza Virus Entry
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Influenza is a major threat to millions of people worldwide. Entry inhibitors are of particular interest for the development of novel therapeutic strategies for influenza. We have previously discovered oleanolic acid (OA) to be a mild influenza hemagglutinin (HA) inhibitor. In this work, inspired by the 3D structure of HA as a homotrimeric receptor, we designed and synthesized 15 OA trimers with different linkers and central region via the copper-catalyzed azide-alkyne cycloaddition reaction. All of the OA trimers were evaluated for their antiviral activities in vitro, and 12c, 12e, 13c, and 13d were observed to exhibit robust potency (IC50 in the submicromolar range) against influenza A/WSN/33 (H1N1) virus that was stronger than that observed with oseltamivir. In addition, these compounds also displayed strong biological activity against A/Hong Kong/4801/2014 and B/Sichuan/531/2018 (BV). The results of hemagglutination inhibition assays and surface plasmon resonance binding assays suggest that these OA trimers may interrupt the interaction between the HA protein of influenza virus and the host cell sialic acid receptor, thus blocking viral entry. These findings highlight the utility of multivalent OA conjugates to enhance the ligand-target interactions in anti-influenza virus drug design and are also helpful for studying antiviral drugs derived from natural products.
- Huang, Boxuan,Li, Weijia,Mu, Yu,Shao, Liang,Su, Yangqing,Sun, Mengsi,Xu, Huan,Yang, Fan,Yu, Fei,Zhang, Jihong,Zhang, Yuan
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p. 1759 - 1765
(2021/11/18)
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- Synthetic method of oxadiargyl (by machine translation)
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The invention discloses a synthetic method, of oxadiargyl, in a non-protonic organic solvent, oxadone phenol is subjected to filtration, distillation to remove the solvent, and then the synthesis method disclosed by the invention is suitable for industrial application, without the addition of the catalyst. with a flammable, explosive chlorine propyne or bromopropyne raw material, in the presence of a catalyst . The synthetic method disclosed by the invention does not need, to be added with a flammable and explosive compound . The synthetic method is suitable for industrial. application. (by machine translation)
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Paragraph 0025; 0026
(2020/02/29)
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- Silica-tethered cuprous acetophenone thiosemicarbazone (STCATSC) as a novel hybrid nano-catalyst for highly efficient synthesis of new 1,2,3-triazolyl-based metronidazole hybrid analogues having potent antigiardial activity
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The preparation, characterization and application of silica-tethered cuprous acetophenone thiosemicarbazone (STCATSC) as a novel hybrid nano catalyst for synthesis of new 1,2,3-triazolyl-based metronidazole hybrid analogues is described. STCATSC is fully
- Soltani Rad, Mohammad?Navid,Behrouz, Somayeh,Mohammadtaghi-Nezhad, Javad,Zarenezhad, Elham,Agholi, Mahmoud
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- Luminescent iridium(iii) complexes of N-heterocyclic carbene ligands prepared using the 'click reaction'
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A series of imidazolium salt, N-heterocyclic carbene (NHC) ligand precursors, combined with 1,2,3-triazoles were synthesized using the Cu(i) catalyzed azide-alkyne cycloaddition 'click reaction'. These pro-ligands were prepared from imidazolium molecules that were functionalized with either a terminal alkyne or azide group. Methylation of the triazole unit with methyl iodide produced a series of imidazolium/triazolium NHC pro-ligands. From these pro-ligands a family of luminescent Ir(iii) complexes of the general form [Ir(ppy)2(C^N)]+ or [Ir(ppy)2(C-C)]+ (where ppy is 2-phenylpyridine and C-N represents a bidentate imidazolylidene/triazole ligand and C-C represents a bidentate imidazolylidene/triazolylidene ligand) were prepared. The electrochemical, photophysical and electrochemiluminescence properties of the complexes have been evaluated and a preliminary study of two of these compounds as luminescent probes for cell imaging studies was conducted in A549 human lung adenocarcinoma basal epithelial cells. Co-localisation studies with the commercial dye MitoTracker CMXRos were consistent with mitochondrial uptake for these compounds.
- Karmis, Rebecca E.,Carrara, Serena,Baxter, Amy A.,Hogan, Conor F.,Hulett, Mark D.,Barnard, Peter J.
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supporting information
p. 9998 - 10010
(2019/07/15)
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- Design, synthesis, and in silico studies of novel eugenyloxy propanol azole derivatives having potent antinociceptive activity and evaluation of their β-adrenoceptor blocking property
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The design, synthesis, antinociceptive and β-adrenoceptor blocking activities of several eugenyloxy propanol azole derivatives have been described. In this synthesis, the reaction of eugenol with epichlorohydrin provided adducts 3 and 4 which were N-alkylated by diverse azoles to obtain the eugenyloxy propanol azole analogues in good yields. Adducts 3 and 4 were also reacted with azide ion to obtain the corresponding azide 6. The ‘Click’ Huisgen cycloaddition reaction of 6 with diverse alkynes afforded the title compounds in good yields. The synthesized eugenyloxy propanol azole derivatives were in vivo studied for the acute antinociception on male Spargue Dawley rats using tail-flick test. Compounds 5f, 5g, 7b and 11a exhibited potent analgesic properties in comparison with eugenol as a standard drug. In addition, all compounds were ex vivo tested for β-adrenoceptor blocking properties on isolated left atrium of male rats which exhibited partial antagonist or agonist behaviour compared to the standard drugs. The molecular docking study on the binding site of transient receptor potential vanilloid subtype 1 (TRPV1) has indicated that like capsaicin, eugenyloxy propanol azole analogues exhibited the strong affinity to bind at site of TPRV1 in a “tail-up, head-down” conformation and the presence of triazolyl moieties has played undeniable role in durable binding of these ligands to TRPV1. The in silico pharmacokinetic profile, drug likeness and toxicity predictions carried out for all compounds determined that 5g can be considered as potential antinociceptive drug candidate for future research.
- Behrouz, Somayeh,Soltani Rad, Mohammad Navid,Taghavi Shahraki, Bahareh,Fathalipour, Mohammad,Behrouz, Marzieh,Mirkhani, Hossein
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p. 147 - 164
(2018/08/22)
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- Synthesis and Reactivity of N-Allenyl Cyanamides
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N-Allenyl cyanamides have been accessed via a one-pot deoxycyanamidation-isomerization approach using propargyl alcohol and N-cyano-N-phenyl-p-methylbenzenesulfonamide. The utility of this novel class of allenamide was explored through derivatization, with hydroarylation, hydroamination, and cycloaddition protocols employed to access an array of cyanamide products that would be challenging to access using existing methods.
- Ayres, James N.,Williams, Matthew T.J.,Tizzard, Graham J.,Coles, Simon J.,Ling, Kenneth B.,Morrill, Louis C.
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supporting information
p. 5282 - 5285
(2018/09/13)
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- Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent
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An alternative method for forming sulfonates through hypervalent iodine(III) reagent-mediated oxidation of sodium sulfinates has been developed. This transformation involves trapping reactive sulfonium species using alcohols. With additional optimization of the reaction conditions, the method appears extendable to other nucleophiles such as electron-rich aromatic systems or cyclic ethers through a ring opening pathway.
- Deruer, Elsa,Hamel, Vincent,Blais, Samuel,Canesi, Sylvain
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supporting information
p. 1203 - 1207
(2018/06/04)
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- Synthesis and in vitro evaluation of dibenzoazepine triazole derivatives: A novel class of antileishmanial agents
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In the present study, a series of dibenzoazepine triazole derivatives (24-39) were synthesized and evaluated for their in vitro bioactivities including antiglycation, antibacterial, DPPH radical scavenging, urease inhibition, antileishmanial and immunomod
- Khan, Maria Aqeel,Saleem, Aliyan,Ghouri, Nida,Hameed, Abdul,Iqbal Choudhary,Basha, Fatima Z.
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p. 597 - 606
(2016/03/22)
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- Click chemistry route to tricyclic monosaccharide triazole hybrids: Design and synthesis of substituted hexahydro-4H-pyrano[2,3-f][1,2,3]triazolo[5,1-c][1,4]oxazepines
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A click chemistry approach to novel tricyclic monosaccharide triazole hybrids, namely, aryl substituted hexahydro-4H-pyrano[2,3-f][1,2,3]triazolo[5,1-c][1,4]oxazepine derivatives from an intramolecular 1,3-dipolar cycloaddition of 6-azido-4-O-propargyl glycopyranosides has been reported.
- Konda, Saidulu,Rao, Pallavi,Oruganti, Srinivas
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p. 63962 - 63965
(2015/02/19)
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- Clickable amphiphilic triblock copolymers
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Amphiphilic polymers have recently garnered much attention due to their potential use in drug delivery and other biomedical applications. A modular synthesis of these polymers is extremely desirable, because it offers precise individual block characteriza
- Isaacman, Michael J.,Barron, Kathryn A.,Theogarajan, Luke S.
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experimental part
p. 2319 - 2329
(2012/07/28)
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- Neomycin-phenolic conjugates: Polycationic amphiphiles with broad-spectrum antibacterial activity, low hemolytic activity and weak serum protein binding
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Here we present a proof-of-concept study, combining two known antimicrobial agents into a hybrid structure in order to develop an emergent cationic detergent-like interaction with the bacterial membrane. Six amphiphilic conjugates were prepared by copper
- Findlay, Brandon,Zhanel, George G.,Schweizer, Frank
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supporting information; experimental part
p. 1499 - 1503
(2012/04/04)
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- Synthesis and photochromic response of a new precisely functionalized chitosan with "clicked" spiropyran
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A new light responsive polysaccharide based on a precisely defined N-phthaloyl chitosan with a covalent bound photochromic spiropyran moiety in C-6 was synthesized through Cu(I) catalyzed azide-alkyne [3 + 2] dipolar cycloaddition between 6-azido-6-deoxy,
- Bertoldo, Monica,Nazzi, Samuele,Zampano, Giovanni,Ciardelli, Francesco
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experimental part
p. 401 - 407
(2012/03/26)
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- Construction of an Artificial Glutathione Peroxidase Active Site on Copolymer Vesicles
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To construct an efficient GPx mimic, a novel method for preparing polymer-based vesicles carrying GPx-active sites was developed. A series of block copolymers loaded with recognition and catalytic sites were synthesized based on polystyrene-block-poly[tri(ethylene glycol) methyl ether acrylate]s (PS-PMEO3MAs). By altering the molar ratio of the functional copolymers, vesicles with GPx activity were obtained by self-assembly of these functional copolymers through blending. The optimum GPx mimic constructed by the blending process exhibited high catalytic activity and acted as a real catalyst with typical saturation kinetics behavior. The method may be of benefit for designing other enzyme mimics and may cast a light on constructing other biologically related functional nanoparticles.Self-assembly of functional copolymers through blending is a novel and simple method to construct efficient glutathione peroxidase(GPx) mimics. The optimum blended GPx mimic is obtained by optimizing the structure of the functional block copolymers and altering the ratio of the functional block copolymers. The blended GPx mimic exhibits remarkable catalytic activity and acts as a real catalyst with typical saturation kinetics behavior.
- Yin, Yanzhen,Huang, Xin,Lv, Chunyan,Wang, Liang,Yu, Shuangjiang,Luo, Quan,Xu, Jiayun,Liu, Junqiu
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experimental part
p. 1505 - 1516
(2011/10/09)
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- Amphiphilic organocatalyst for schotten-baumann-type tosylation of alcohols under organic solvent free condition
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A Tosylation of primary alcohol with tosyl chloride was performed effectively with an W-hexadecylimidazole catalyst in water containing K 2CO3 aggregation of the catalyst carrying a hydrophobic methylene chain worked as a substitute for organic solvent.
- Asano, Keisuke,Matsubara, Seijiro
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supporting information; experimental part
p. 1757 - 1759
(2009/09/06)
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- Aza cope rearrangement of propargyl enammonium cations catalyzed by a self-assembled "nanozyme"
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The tetrahedral assembly [Ga4L6]12- [L = N,N-bis(2,3-dihydroxybenzoyl)-1,5-diaminonaphthalene) encapsulates a variety of cations, including propargyl enammonium cations capable of undergoing the aza Cope rearrangement. For propargyl enammonium substrates that are encapsulated in the [Ga4L6]12- assembly, rate accelerations by factors of up to 184 compared with the background reaction rate were observed. After rearrangement, the product iminium ion is released into solution and hydrolyzed, allowing for catalytic turnover. The activation parameters for the catalyzed and uncatalyzed reaction were determined, revealing that a decrease in the entropy of activation is responsible for the observed rate enhancements. The catalyzed reaction exhibits saturation kinetics: the rate data obeyed the Michaelis-Menten model of enzyme kinetics, and competitive inhibition using a nonreactive guest was demonstrated.
- Hastings, Courtney J.,Fiedler, Dorothea,Bergman, Robert G.,Raymond, Kenneth N.
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supporting information; experimental part
p. 10977 - 10983
(2009/02/05)
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- Rapid assembly and in situ screening of bidentate inhibitors of protein tyrosine phosphatases
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We have successfully designed and synthesized a small library of protein tyrosine phosphatase (PTP) inhibitors, in which the so-called "click chemistry" or Cu(I)-catalyzed 1,3-dipolar alkyne-azide coupling reaction was carried out for rapid assembly of 66 different bidentate compounds. Subsequent in situ enzymatic screening revealed a potential PTP1B inhibitor (IC50 = 4.7 μM) which is 10-100 fold more potent than other PTPs.
- Srinivasan, Rajavel,Uttamchandani, Mahesh,Yao, Shao Q.
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p. 713 - 716
(2007/10/03)
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- Novel pyrazines from the myxobacterium Chondromyces crocatus and marine bacteria
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The volatiles released by two strains of the myxobacterium Chondromyces crocatus and seven strains of marine Alpha-proteobacteria from the North Sea were collected using the CLSA or SPME headspace methods and analysed by GC-MS. In the extracts of C. crocatus 27 pyrazines were identified, belonging to different classes. 2,5-Dialkylpyrazines and related 3-methoxy-2,5- dialkylpyrazines dominated. Several pyrazines like 2-(1-methylethenyl)-5-(1- methylethyl)-pyrazine (7) and 3-methoxy-2,5-dialkylpyrazines with methyl, isopropyl, isobutyl or sec-butyl side-chains were obtained from natural sources for the first time. It was essential for the identification to rely on synthetic reference materials, which were obtained using Fuerstner's iron-catalysed coupling of chloropyrazines with Grignard reagents or condensation of azido ketones as key steps. The synthetic material allowed the identification of two previously unknown attractants of bacterial origin for the pineapple beetle Carpophilus humeralis, namely 3-methoxy-2-(1-methylpropyl)-5-(2-methylpropyl) pyrazine (17) and 3-methoxy-2,5-bis(1-methylpropyl)pyrazine (52). Several 2,5-dialkylpyrazines were identified in the extracts of the marine Alphaproteobacteria. The unique 2,5-dimethyl-3-(methylsulfanyl)pyrazine (67) represents a new type of natural pyrazine. Our results, together with literature reports, show that pyrazines are an important class of bacterial volatiles which might be more widespread than previously thought. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
- Dickschat, Jeroen S.,Reichenbach, Hans,Wagner-Doebler, Irene,Schulz, Stefan
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p. 4141 - 4153
(2007/10/03)
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- Platinum- and gold-catalyzed cycloisomerization reactions of hydroxylated enynes
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Exposure of enynes containing a hydroxyl group at one of the propargylic positions to catalytic amounts of either PtCl2 or (PPh3)AuCl/AgSbF6 results in a selective rearrangement with formation of bicyclo[3.1.0]hexan-3-one
- Mamane, Victor,Gress, Tobias,Krause, Helga,Fuerstner, Alois
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p. 8654 - 8655
(2007/10/03)
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- Intramolecular palladium(II)-catalyzed 1,2-addition to allenes
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Palladium(II)-catalyzed intramolecular 1,2-additions to allenes substituted with an internal nucleophile have been developed. Carboxylic acids, alcohols, N-substituted amides, and carbamates were used as internal nucleophiles in the palladium-catalyzed re
- Jonasson,Horvath,Backvall
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p. 9600 - 9609
(2007/10/03)
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- Process for producing 1-substituted-hydantoins
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The subject is to provides a process for producing 1-substituted-hydantoins of Formula I: STR1 wherein R1 represents d hydrocarbon group which may be substituted and others, cheracterized by reacting N-sustituted-N-alkcycarbonylamnilo-acetonitrile of Formula II: STR2 wherein R2 represents an alkyl group and others, with an alkali metal hydroxides or the like and then treating with an acid.
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- Process for producing 1-substituted-hydantoins
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The subject is to provides a process for producing 1-substituted-hydantoins of Formula I: wherein R1represents a hydrocarbon group which may be substituted and others,characterized by reacting N-substituted-N-alkoxycarbonylamino-acetonitrile of Formula II: wherein R2represents an alkyl group and others,with an alkali metal hydroxides or the like and then treating with an acid.
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- Practical and Safe Sulfonylation of 2-Alkynyl and 2-Alkenyl Alcohols Using the Combined Bases of a Catalytic Amount of Tertiary Amine and Potassium Carbonate
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Several 2-alkynyl and 2-alkenyl alcohols were effectively sulfonylated with methanesulfonyl chloride or p-toluenesulfonyl chloride using the combined bases of a catalytic amount of tertiary amine and potassium carbonate.The reaction was conducted with reliable safety and while avoiding the disposal of wasted amines.The mesylation of 2-propyn-1-ol proceeded on a large scale (more than 20 kg) without a substantial production of explosive 3-chloro-1-propyne.The choice of the catalysts was important, and sterically unhindered tertiary amines, such as trimethylamine, N,N-d imethylbenzylamine, and triethylamine, were effective.Without these catalysts the reactions were significantly retarded.The reaction was so mild that it could be applied to complex and optically active 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one, which is an important alcohol moiety of synthetic pyrethroids.
- Tanabe, Yoo,Yamamoto, Hitomi,Yoshida, Yoshihiro,Miyawaki, Takashi,Utsumi, Naoka
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p. 297 - 300
(2007/10/02)
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- Synthesis of Enantiomerically Pure Unsaturated α-Amino Acids Using Serine-Derived Zinc/Copper Reagents
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Treatment of the serine-derived organozinc reagent 2, in benzene/dimethylacetamide, with a THF solution of CuCN*2LiCl gives rise to a zinc/copper reagent 6 which reacts directly with allylic halides and tosylates to give the corresponding enantiomerically pure substitution products 9 in 32-65percent yield (11 examples).The reaction proceeds by formal SN2' displacement of the leaving group.Reaction with propargyl halides gives the corresponding terminal allene 12a.The zinc reagent 2 may also be prepared directly from protected iodoalanine 1 in THF by the Knochel method.Reaction with propargylic tosylates as electrophiles gives rise to the corresponding protected terminal allenic amino acids in 51-81percent yield (four examples); use of enantiomerically enriched propargylic tosylates results in the formation of diastereoisomerically enriched allenic products.Reactions of the zinc/copper reagent 6 with a range of representative electrophiles is explored; use of relatively reactive electrophiles is necessary to obtain satisfactory yields.Finally, the possibility of using the serine-derived iodide 20, in which the carboxylic acid is protected as a methyl ester, is established.This reagent offers advantages over the corresponding benzyl ester protected reagent 6 for the synthesis of unsaturated amino acids.
- Dunn, Michael J.,Jackson, Richard F. W.,Pietruszka, Joerg,Turner, Debra
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p. 2210 - 2215
(2007/10/02)
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- Palladium-catalyzed coupling of stannyl allenes with aryl iodides
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Substituted allenes are prepared by coupling stannyl allenes with aryl iodides under palladium(0) catalysis. A concise and versatile sequence starting from propargyl alcohols provides a route for the preparation of substituted allenes under extremely mild conditions.
- Aidhen,Braslau
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p. 789 - 797
(2007/10/02)
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- KINETICS AND MECHANISM OF AMINOLYSIS OF PROPARGYL AND 1-METHYL-PROPARGYL ARENESULPHONATES
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Kinetic studies were carried out on the aminolysis of propargyl and 1-methylpropargyl arenesulphonates in acetonitrile at 45.0 deg C.The cross-interaction constants, ρxz and βxz, are similar to, but smaller than, those for the SN2 processes at other primary and secondary carbon centers.Compared with the allyl series, the smaller magnitude of ρxz and βxz reflects a looser transition state, which in turn leads to a lower rate despite the greater Taft's ?* value and the lower intrinsic (ΔE0) and thermodynamic barriers (ΔE0).
- Oh, Hyuck Keun,Cho, In Ho,Jin, Min Jeong,Lee, Ikchoon
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p. 629 - 633
(2007/10/02)
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- Cyclisation des alcools δ-alleniques par le nitrate d'argent ou les sels mercuriques. Synthese d'α-alcenyl-2 tetrahydropyrannes
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Eight diversely substituted δ-allenic alcohols have been synthesized by using three different methods for the formation of the allenic linkage.When treated with silver nitrate or mercuric salts, these alcohols are transformed in fairly good yields into α-alkenyl-2 tetrahydropyrans.In addition to its regioselectivity in the formation of the heterocycle this reaction shows in certain cases a high stereoselectivity.Alcohols monosubstituted on the thermal allenic carbon lead to more than 90percent of the E product whereas the 2,4 or 2,6 disubstituted tetrahydropyrans are obtained in predominantly the Z configuration.
- Audin, Patrick,Doutheau, Alain,Gore, Jacques
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p. 297 - 306
(2007/10/02)
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