- Hypervalent iodine(iii) induced oxidative olefination of benzylamines using Wittig reagents
-
We have developed hypervalent iodine(iii) induced oxidative olefination of primary and secondary benzylamines using 2C-Wittig reagents, which provides easy access to α,β-unsaturated esters. Mild reaction conditions, good to excellent yields with high (E) selectivity, and a broad substrate scope are the key features of this reaction. We have successfully carried out the gram-scale synthesis of α,β-unsaturated esters.
- Ramavath, Vijayalakshmi,Rupanawar, Bapurao D.,More, Satish G.,Bansode, Ajay H.,Suryavanshi, Gurunath
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p. 8806 - 8813
(2021/05/26)
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- Stereodivergent Nucleophilic Additions to Racemic β-Oxo Acid Derivatives: Fast Addition Outcompetes Stereoconvergence in the Archetypal Configurationally Unstable Electrophile
-
Additions of carbon nucleophiles to racemic α-stereogenic β-oxo acid derivatives that deliver enantiomerically enriched tertiary alcohols are valuable, but uncommon. This article describes stereodivergent Cu-catalyzed borylative cyclizations of racemic β-oxo acid derivatives bearing tethered pro-nucleophilic olefins to deliver highly functionalized cyclopentanols containing four contiguous stereogenic centers. The reported protocol is applicable to a range of β-oxo acid derivatives, and the diastereomeric products are readily isolable by typical chromatographic techniques. α-Stereogenic-β-keto esters are typically thought to have extreme or spontaneous configurational fragility, but mechanistic studies for this system reveal an unusual scenario wherein productive catalysis occurs on the same time scale as background substrate racemization and completely outcompetes on-cycle epimerization, even under the basic conditions of the reaction.
- Crawford, Evan T.,De Jesús Cruz, Pedro,Johnson, Jeffrey S.,Liu, Shubin
-
supporting information
p. 16264 - 16273
(2021/10/21)
-
- GPR35 MODULATORS
-
Described herein are GPR35 modulators and methods of using these compounds in the treatment of diseases, disorders or conditions. Also described herein are pharmaceutical compositions containing such compounds.
- -
-
Paragraph 00330
(2020/08/13)
-
- Metal-free domino Cloke-Wilson rearrangement-hydration-dimerization of cyclopropane carbaldehydes: A facile access to oxybis(2-aryltetrahydrofuran) derivatives
-
In this work, we have demonstrated a metal-free transformation of cyclopropane carbaldehydes to oxybis(2-aryltetrahydrofuran) derivatives via a domino Cloke-Wilson rearrangement-hydration-dimerization sequence. Commercially inexpensive p-toluene sulfonic acid (PTSA) was used as a Br?nsted acid catalyst, and reactions were conducted in an open-flask. Detection of reaction intermediates were carried to get an insight into the reaction pathway.
- Banerjee, Prabal,Dey, Raghunath,Rajput, Shruti
-
-
- COMPOUNDS
-
The invention provides a polymyxin compound of formula (I) and salts, solvates and protected forms thereof, pharmaceutical compositions comprising the compounds of formula (I), and the use of the compounds and compositions in methods of treatment, such as
- -
-
Page/Page column 49
(2020/01/24)
-
- Enantioselective Syntheses of Strychnos and Chelidonium Alkaloids through Regio- and Stereocontrolled Cooperative Catalysis
-
We describe enantioselective syntheses of strychnos and chelidonium alkaloids. In the first case, indole acetic acid esters were established as excellent partner nucleophiles for enantioselective cooperative isothiourea/Pd catalyzed α-alkylation. This provides products containing indole-bearing stereocenters in high yield and with excellent levels of enantioinduction in a manner that is notably independent of the N-substituent. This led to concise syntheses of (?)-akuammicine and (?)-strychnine. In the second case, the poor performance of ortho-substituted cinnamyl electrophiles in the enantioselective cooperative isothiourea/Ir catalyzed α-alkylation was overcome by appropriate substituent choice, leading to enantioselective syntheses of (+)-chelidonine, (+)-norchelidonine, and (+)-chelamine.
- Fyfe, James W. B.,Hutchings-Goetz, Luke S.,Snaddon, Thomas N.,Yang, Chao
-
supporting information
p. 17556 - 17564
(2020/08/14)
-
- Sequential Palladium-Catalyzed Allylic Alkylation/retro-Dieckmann Fragmentation Strategy for the Synthesis of α-Substituted Acrylonitriles
-
A straightforward synthesis of α-substituted acrylonitriles is described using 4-cyano-3-oxotetrahydro-thiophene (c-THT) as an acrylonitrile surrogate. This unprecedented two-step sequence featuring a palladium-catalyzed allylic alkylation (Pd-AA) and a retro-Dieckmann fragmentation provides a general entry into diversely substituted 1,4-dienes.
- Katsina, Tania,Sharma, Sachi Prem,Buccafusca, Roberto,Quinn, Derek J.,Moody, Thomas S.,Arseniyadis, Stellios
-
supporting information
p. 9348 - 9352
(2019/11/20)
-
- Highly Enantioselective, Base-Free Synthesis of α-Quaternary Succinimides through Catalytic Asymmetric Allylic Alkylation
-
The synthesis of diversely substituted five-membered ring succinimide derivatives is reported featuring a direct, base-free, palladium-catalyzed asymmetric allylic alkylation. The method allows a straightforward access to the desired heterocyclic scaffold bearing an all-carbon α-quaternary stereogenic center in high yields and good to excellent enantioselectivities. To further demonstrate the synthetic utility of the method, the allylated products were further converted to various versatile chiral building blocks, including a chiral pyrrolidine and a spirocyclic derivative, using selective transformations.
- Song, Tao,Arseniyadis, Stellios,Cossy, Janine
-
supporting information
p. 8076 - 8080
(2018/06/15)
-
- One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts
-
A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O 2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO 2 Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.
- Ding, Weijie,Hu, Juan,Jin, Huile,Yu, Xiaochun,Wang, Shun
-
p. 107 - 118
(2017/09/28)
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- Facile synthesis of α, β-unsaturated esters through a one-pot copper-catalyzed aerobic oxidation-Wittig reaction
-
An efficient one-pot synthesis of α, β-unsaturated esters through the aerobic oxidation – Wittig tandem reaction of alcohols and phosphorous ylide is developed. This new method operates under mild reaction conditions, and uses CuI/TEMPO (TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) as co-catalyst and air (O2) as the oxidant. It tolerates a wide range of functionalized benzylic alcohol and aliphatic alcohols.
- Ren, Cheng,Shi, Zhenyu,Ding, Weijie,Liu, Zhiqing,Jin, Huile,Yu, Xiaochun,Wang, Shun
-
supporting information
p. 14 - 17
(2017/12/06)
-
- Propionic Acid Derivatives and Methods of Use Thereof
-
Provided herein are compounds and pharmaceutical compositions of formula I where R1, R2, R3, R4, R5 and R6 are as described herein. Also provided pharmaceutically acceptable salts or stereoisomers of these compounds. In addition methods are provided for inhibiting the binding of an integrin to treat various pathophysiological conditions.
- -
-
Paragraph 0713; 0730
(2018/11/21)
-
- Rh(III)-Catalyzed Enaminone-Directed C-H Coupling with α-Diazo-α-phosphonoacetate for Reactivity Discovery: Fluoride-Mediated Dephosphonation for C-C Coupling Reactions
-
Rh(III)-catalyzed enaminone-directed C-H coupling with α-diazo-α-phosphonoacetate has been used for the identification of fluoride-mediated dephosphonation C-C coupling reactivity for the synthesis of 4-hydroxy-1-naphthoates. Intermolecular C-C coupling of α-phosphonoacetate and benzaldehyde for (E)-selective α,β-unsaturated ester synthesis has also been achieved.
- Song, Chao,Yang, Chen,Zeng, Hua,Zhang, Wenjing,Guo, Shan,Zhu, Jin
-
supporting information
p. 3819 - 3823
(2018/07/22)
-
- Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes
-
The stereoselective synthesis of syn-β-fluoroaziridine building blocks via chiral aryl iodide-catalyzed fluorination of allylic amines is reported. The method employs HF-pyridine as a nucleophilic fluoride source together with mCPBA as a stoichiometric oxidant, and affords access to arylethylamine derivatives featuring fluorine-containing stereocenters in high diastereo- and enantioselectivity. Catalyst-controlled diastereoselectivity in the fluorination of chiral allylic amines enabled the preparation of highly enantioenriched 1,3-difluoro-2-amines bearing three contiguous stereocenters. The enantioselective catalytic method was applied successfully to other classes of multifunctional alkene substrates to afford anti-β-fluoropyrrolidines, as well as a variety of 1,2-oxyfluorinated products.
- Mennie, Katrina M.,Banik, Steven M.,Reichert, Elaine C.,Jacobsen, Eric N.
-
supporting information
p. 4797 - 4802
(2018/04/17)
-
- Propionic Acid Derivatives and Methods of Use Thereof
-
Provided herein are compounds and pharmaceutical compositions of formula I where R1, R2, R3, R4, R5, X and R6 are as described herein. Also provided pharmaceutically acceptable salts or stereoisomer(s) of these compounds. In addition methods are provided for antagonizing the action of an α4-integrin to treat various pathophysiological conditions.
- -
-
Paragraph 0304; 0305
(2018/11/21)
-
- Efficient synthesis of functionalized olefins by Wittig reaction using Amberlite resin as a mild base
-
A convenient procedure for the synthesis of olefins by the reaction of stabilized, semistabilized, and nonstabilized phosphorous ylides with various aldehydes or ketone using Amberlite resin as a mild base is described. Our developed method offers facile and racemization-free synthesis of α,β-unsaturated amino esters and chiral allylic amine. The developed methodology offers mild reaction conditions, high efficiency, and facile isolation of the final products, a practical alternative to known procedures.
- Valkute, Tushar R.,Aratikatla, Eswar K.,Bhattacharya, Asish K.
-
p. 581 - 589
(2017/03/15)
-
- N-heterocyclic carbene-catalysed Peterson olefination reaction
-
N-heterocyclic carbenes (NHCs) have been utilised as highly efficient organocatalysts to catalyse Peterson olefination reaction of aldehydes with trimethylsilylketene ethyl trimethylsilyl acetal or fluoro(trimethylsilyl)ketene ethyl trimethylsilyl acetal to produce the corresponding functionalized olefines in 34-93% yields with excellent stereoselectivities.
- Wang, Ying,Du, Guang-Fen,Gu, Cheng-Zhi,Xing, Fen,Dai, Bin,He, Lin
-
p. 472 - 478
(2015/12/31)
-
- Compositions containing ionic liquids and their uses, in particular in organic synthesis
-
An ionic liquid is used as liquid matrix for organic synthesis in homogeneous phase on soluble support, the ionic liquid being presented in liquid or solid form at ambient temperature, of formula A1+X1?, A1+ representing a cation, functional or non-functional, or a mixture of cations in which either none of the cations is functional or at least one of the cations is functional, and X1? an anion, functional or non-functional, or a mixture of anions in which either none of the anions is functional or at least one of the anions is functional.
- -
-
Page/Page column 45; 46; 47; 48
(2016/10/17)
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- Tandem oxidation–Wittig reaction using nanocrystalline barium manganate (BaMnO4); an improved one-pot protocol
-
A one-pot, tandem oxidation–Wittig procedure has been developed in which the reacting components are generated in situ from alcohols, triphenyl phosphine, and ethyl bromoacetate using barium manganate as a mild oxidizing agent without the addition of an external base.
- Gholinejad, Mohammad,Firouzabadi, Habib,Bahrami, Maedeh,Nájera, Carmen
-
supporting information
p. 3773 - 3775
(2016/07/26)
-
- Dual [Fe+Phosphine] catalysis: Application in catalytic wittig olefination
-
Iron hydride complexes of the general formula P2Fe(NO)CO)H are highly active catalysts for the hydrosilylation of aldehydes or ketones and phosphine oxides. Depending on the solvent, the in situ reduction of the phosphine oxide can be faster than the corresponding hydrosilylation of a carbonyl group. This unusual activity was used within the context of catalytic Wittig olefination. Picture perfect: Iron hydride complexes of the general formula P2Fe(NO)CO)H are highly active catalysts for the hydrosilylation of aldehydes or ketones and phosphine oxides. Depending on the solvent, the in situ reduction of the phosphine oxide can be faster than the corresponding hydrosilylation of a carbonyl group. This unusual activity is used within the context of catalytic Wittig olefination. EWG=Electron-withdrawing group.
- Rommel, Susanne,Belger, Christian,Begouin, Jeanne-Marie,Plietker, Bernd
-
p. 1292 - 1301
(2015/04/27)
-
- Dialkylzinc-mediated allylic polyfluoroarylation reaction
-
Abstract We present an allylic polyfluoroarylation reaction with broad substrate scope and excellent functional group tolerance, using organozinc reagents under mild conditions. A catalytic amount of triphenylphosphine oxide efficiently promotes iodine-zinc exchange reaction between polyfluoroaryl iodide and dimethylzinc, and the resulting phosphine oxide-activated polyfluoroarylzinc undergoes substitution reaction with allylic halides to afford the corresponding polyfluoroarylated products.
- Kurauchi, Daisuke,Hirano, Keiichi,Kato, Hisano,Saito, Tatsuo,Miyamoto, Kazunori,Uchiyama, Masanobu
-
supporting information
p. 5849 - 5857
(2015/08/03)
-
- An isothiourea-catalyzed asymmetric [2,3]-rearrangement of allylic ammonium ylides
-
Benzotetramisole promotes the catalytic asymmetric [2,3]-rearrangement of allylic quaternary ammonium salts (either isolated or prepared in situ from p-nitrophenyl bromoacetate and the corresponding allylic amine), generating syn-α-amino acid derivatives with excellent diastereo- and enantioselectivity (up to >95:5 dr; up to >99% ee).
- West, Thomas H.,Daniels, David S. B.,Slawin, Alexandra M. Z.,Smith, Andrew D.
-
supporting information
p. 4476 - 4479
(2014/04/17)
-
- Synthetic variants of mycolactone bind and activate Wiskott-Aldrich syndrome proteins
-
Mycolactone is a complex macrolide toxin produced by Mycobacterium ulcerans, the causative agent of skin lesions called Buruli ulcers. Mycolactone-mediated activation of neural (N) Wiskott-Aldrich syndrome proteins (WASP) induces defects in cell adhesion underpinning cytotoxicity and disease pathogenesis. We describe the chemical synthesis of 23 novel mycolactone analogues that differ in structure and modular assembly of the lactone core with its northern and southern polyketide side chains. The lactone core linked to southern chain was the minimal structure binding N-WASP and hematopoietic homolog WASP, where the number and configuration of hydroxyl groups on the acyl side chain impacted the degree of binding. A fluorescent derivative of this compound showed time-dependent accumulation in target cells. Furthermore, a simplified version of mycolactone mimicked the natural toxin for activation of WASP in vitro and induced comparable alterations of epithelial cell adhesion. Therefore, it constitutes a structural and functional surrogate of mycolactone for WASP/N-WASP-dependent effects.
- Chany, Anne-Caroline,Veyron-Churlet, Romain,Tresse, Cédric,Mayau, Véronique,Casarotto, Virginie,Le Chevalier, Fabien,Guenin-Macé, Laure,Demangel, Caroline,Blanchard, Nicolas
-
p. 7382 - 7395
(2014/12/11)
-
- TRIAZOLONE COMPOUNDS AND USES THEREOF
-
The invention disclosed herein is directed to compounds of Formula (I) and pharmaceutically acceptable salts thereof, which are useful in the treatment of prostate, breast, colon, pancreatic, human chronic lymphocytic leukemia, melanoma and other cancers. The invention also comprises pharmaceutical compositions comprising a therapeutically effective amount of compound of Formula (I), or a pharmaceutically acceptable salt thereof. The invention disclosed herein is also directed to methods of treating prostate, breast, ovarian, liver, kidney, colon, pancreatic, human chronic lymphocytic leukemia, melanoma and other cancers. The invention disclosed herein is further directed to methods of treating prostate, breast, colon, pancreatic, chronic lymphocytic leukemia, melanoma and other cancers comprising administration of a of a therapeutically effective amount of a selective PPARα antagonist. The compounds and pharmaceutical compositions of the invention are also useful in the treatment of viral infections, such as HCV infections and HIV infections. The invention disclosed herein is also directed to a methods of preventing the onset of and/or recurrence of acute and chronic myeloid leukemia, as well as other cancers, comprising administration of a of a therapeutically effective amount of a selective PPARα antagonist.
- -
-
Paragraph 00185
(2013/09/26)
-
- Modeling, synthesis, and biological evaluation of potential retinoid X receptor (RXR) selective agonists: Novel analogues of 4-[1-(3,5,5,8,8- Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene) and (E)-3-(3-(1,2,3,4-tetrahydro-1,1,
-
Three unreported analogues of 4-[1-(3,5,5,8,8-pentamethyl-5-6-7-8- tetrahydro-2-naphthyl)ethynyl]benzoic acid (1), otherwise known as bexarotene, as well as four novel analogues of (E)-3-(3-(1,2,3,4-tetrahydro-1,1,4,4,6- pentamethylnaphthalen-7-yl)-4-hydr
- Jurutka, Peter W.,Kaneko, Ichiro,Yang, Joanna,Bhogal, Jaskaran S.,Swierski, Johnathon C.,Tabacaru, Christa R.,Montano, Luis A.,Huynh, Chanh C.,Jama, Rabia A.,Mahelona, Ryan D.,Sarnowski, Joseph T.,Marcus, Lisa M.,Quezada, Alexis,Lemming, Brittney,Tedesco, Maria A.,Fischer, Audra J.,Mohamed, Said A.,Ziller, Joseph W.,Ma, Ning,Gray, Geoffrey M.,Van Der Vaart, Arjan,Marshall, Pamela A.,Wagner, Carl E.
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p. 8432 - 8454
(2013/12/04)
-
- Novel symmetrical ureas as modulators of protein arginine methyl transferases
-
Methylation of histone arginine residues is an epigenetic mark related to gene expression that is implicated in a variety of biological processes and can be reversed by small-molecule modulators of protein arginine methyltransferases (PRMTs). A series of symmetrical ureas, designed as analogues of the known PRMT1 inhibitor AMI-1 have been synthesized using Pd-catalyzed Ar-N amide bond formation processes or carbonylation reactions as key steps. Their inhibitory profile has been characterized. The enzymatic assays showed a weak effect on PRMT1 and PRMT5 activity for most of the compounds. The acyclic urea that exhibited the strongest effect on the inhibition of the PRMT1 activity also showed the greatest effect on the expression of some androgen receptor target genes (TMPRSS2 and FKBP5), which may be related with its enzymatic activity. Surprisingly, AMI-1 behaved as an activator of PRMT5 activity, a result not reported so far.
- Fontán, Noelia,García-Domínguez, Patricia,álvarez, Rosana,De Lera, ángel R.
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p. 2056 - 2067
(2013/05/09)
-
- Design, synthesis, and biological evaluation of potent and selective class IIa histone deacetylase (HDAC) inhibitors as a potential therapy for huntington's disease
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Inhibition of class IIa histone deacetylase (HDAC) enzymes have been suggested as a therapeutic strategy for a number of diseases, including Huntington's disease. Catalytic-site small molecule inhibitors of the class IIa HDAC4, -5, -7, and -9 were developed. These trisubstituted diarylcyclopropanehydroxamic acids were designed to exploit a lower pocket that is characteristic for the class IIa HDACs, not present in other HDAC classes. Selected inhibitors were cocrystallized with the catalytic domain of human HDAC4. We describe the first HDAC4 catalytic domain crystal structure in a "closed-loop" form, which in our view represents the biologically relevant conformation. We have demonstrated that these molecules can differentiate class IIa HDACs from class I and class IIb subtypes. They exhibited pharmacokinetic properties that should enable the assessment of their therapeutic benefit in both peripheral and CNS disorders. These selective inhibitors provide a means for evaluating potential efficacy in preclinical models in vivo.
- Bürli, Roland W.,Luckhurst, Christopher A.,Aziz, Omar,Matthews, Kim L.,Yates, Dawn,Lyons, Kathy. A.,Beconi, Maria,McAllister, George,Breccia, Perla,Stott, Andrew J.,Penrose, Stephen D.,Wall, Michael,Lamers, Marieke,Leonard, Philip,Müller, Ilka,Richardson, Christine M.,Jarvis, Rebecca,Stones, Liz,Hughes, Samantha,Wishart, Grant,Haughan, Alan F.,O'Connell, Catherine,Mead, Tania,McNeil, Hannah,Vann, Julie,Mangette, John,Maillard, Michel,Beaumont, Vahri,Munoz-Sanjuan, Ignacio,Dominguez, Celia
-
supporting information
p. 9934 - 9954
(2014/01/17)
-
- HISTONE DEACETYLASE INHIBITORS AND COMPOSITIONS AND METHODS OF USE THEREOF
-
Provided are certain histone deacetylase (HDAC) inhibitors of Formula I, compositions thereof, and methods of their use.
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-
Page/Page column 65; 66
(2012/08/08)
-
- Microwave-accelerated Wittig olefination of β-chloroacroleins
-
The first microwave assisted Wittig reactions of β-chloroacroleins with a stabilized ylide are described here. A combination of sodium ethoxide and toluene was found to be optimum and using this reaction condition a number of alkenyl-substituted benzopyra
- Bera, Rabin,Dhananjaya,Singh, Shambu Nath,Kumar, Rajender,Mukkanti,Pal, Manojit
-
experimental part
p. 1300 - 1305
(2009/04/18)
-
- Synthesis of catechins via thiourea/AuCl3-catalyzed cycloalkylation of aryl epoxides
-
(Chemical Equation Presented) A diversity-oriented approach for the synthesis of structurally diverse catechins was achieved in good yields via thiourea/AuCl3/AgOTf-catalyzed annulations of aryl epoxides under mild conditions. This new protocol provides a highly efficient entry to a library of catechins-derived natural products, notably anti-HIV agent 8-C-ascorbyl-(-)-epigallocatechin.
- Liu, Yongxiang,Li, Xiben,Lin, Guang,Xiang, Zheng,Xiang, Jing,Zhao, Mingzhe,Chen, Jiahua,Yang, Zhen
-
p. 4625 - 4629
(2008/09/20)
-
- Substituted 3-phenylpropenoates and related analogs: Electron ionization mass spectral fragmentation and density functional theory calculations
-
Analysis of ethyl 3-(2-chlorophenyl)propenoate by electron ionization mass spectrometry showed the distinct loss of an ortho chlorine. To characterize the structural requisites for the observed mass fragmentation, a series of 30 halogen-substituted 3-phenylpropenoate-related structures were examined. All ester-containing alkene derivatives exhibited loss of the distinctive chlorine from the 2-position of the phenyl ring. Analogous derivatives with the halogen (chlorine or bromine) in the para position did not evidence selective halogen loss. Results demonstrated that substituted 3-phenylpropenoates and their analogs fragment via the formation of a previously reported benzopyrylium intermediate. To understand the correlation between the intramolecular radical substitution and the abundance and selectivity of the chlorine (or other halogen) displacement, density functional theory calculations were performed to determine the charge on the principal cation involved in the chlorine loss (in the ortho, meta, and para positions), the charge for the neutral radical (noncation), the excess alpha-electron density on the relevant atom and the energy to form the cation from the neutral atom (ionization energy). Results showed that the selectivity and extent of halogen displacement correlated highly to the electrophilicity of the radical cation as well as the neutral radical. These data further support the proposed fragmentation mechanism involving intramolecular radical elimination. Copyright
- Wheelock,Colvin,Sanborn,Hammock
-
scheme or table
p. 1053 - 1062
(2009/07/04)
-
- Phenylaminopropanol derivatives and methods of their use
-
The present invention is directed to phenylaminopropanol derivatives of formula I: or a pharmaceutically acceptable salt thereof, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions ameliorated by monoamine reuptake including, inter alia, vasomotor symptoms (VMS), sexual dysfunction, gastrointestinal and genitourinary disorders, chronic fatigue syndrome, fibromylagia syndrome, nervous system disorders, and combinations thereof, particularly those conditions selected from the group consisting of major depressive disorder, vasomotor symptoms, stress and urge urinary incontinence, fibromyalgia, pain, diabetic neuropathy, and combinations thereof.
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Page/Page column 40
(2008/06/13)
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- Pd(OAc)2-Catalyzed Oxidative Coupling Reaction of Benzenes with Olefins in the Presence of Molybdovanadophosphoric Acid under Atmospheric Dioxygen and Air
-
The direct oxidative coupling reaction of benzenes with alkenes bearing an electron-withdrawing group was successfully achieved by the use of Pd(OAc) 2/molybdovanadophosphoric acid (HPMoV) as the key catalyst under O2 or air atmosphere. Thus, the reaction of benzene with ethyl acrylate under air (1 atm) assisted by Pd(OAc)2/HPMoV afforded ethyl cinnamate as a major product in satisfactory yield (74%). This catalytic system could be extended to the coupling reactions between various substituted benzenes and alkenes through the direct aromatic C-H bond activation. In the reaction of benzene with ethyl acrylate under O2 (1 atm), the best turn-over number (TON) of Pd(OAc)2 reached was 121. This reaction provides a green route to cinnamate derivatives, which are important precursors of a variety of pharmaceuticals.
- Tani, Masayuki,Sakaguchi, Satoshi,Ishii, Yasutaka
-
p. 1221 - 1226
(2007/10/03)
-
- Ruthenium-Catalyzed Heck-Type Olefination and Suzuki Coupling Reactions: Studies on the Nature of Catalytic Species
-
Ruthenium-catalyzed Heck olefination and Suzuki cross coupling reactions have been developed. When starting with a ruthenium complex [RuCl 2(p-cymene)]2 as a homogeneous catalyst precursor, induction periods were observed and ruthenium colloids of zero oxidation state were generated under catalytic conditions. Isolated ruthenium colloids carried out the olefination, implying that active catalytic species are ruthenium nanoclusters. To support this hypothesis, ruthenium nanoparticles stabilized with dodecylamine were independently prepared via a hydride reduction procedure, and their catalytic activity was subsequently examined. Olefination of iodobenzene with ethyl acrylate was efficiently catalyzed by the ruthenium nanoparticles under the same conditions, which could be also reused for the next runs. In poisoning experiments, the conversion of the olefination was completely inhibited in the presence of mercury, thus supporting our assumption on the nature of catalytic species. No residual ruthenium was detected from the filtrate at the end of the reaction. On the basis of the postulation, a heterogeneous catalyst system of ruthenium supported on alumina was consequently developed for the Heck olefination and Suzuki cross coupling reactions for the first time. It turned out that substrate scope and selectivity were significantly improved with the external ligand-free catalyst even under milder reaction conditions when compared to results with the homogeneous precatalyst. It was also observed that the immobilized ruthenium catalyst was recovered and reused up to several runs with consistent efficiency. Especially in the Suzuki couplings, the reactions could be efficiently carried out with as low as 1 molpercent of the supported catalyst over a wide range of substrates and were scaled up to a few grams without any practical problems, giving coupled products with high purity by a simple workup procedure.
- Na, Youngim,Park, Soyoung,Han, Soo Bong,Han, Hoon,Ko, Sangwon,Chang, Sukbok
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p. 250 - 258
(2007/10/03)
-
- Horner-Emmons synthesis with minimal purification using ROMPGEL: A novel high-loading matrix for supported reagents
-
(Matrix presented) The synthesis and use of two novel high-loading Horner-Emmons ring-opening metathesis polymers are described. α,β-Unsaturated ethyl esters (E:Z> 99:1) and α,β-unsaturated nitriles (E:Z> 70:30) are obtained in excellent yields and purities from aldehydes with minimal purification.
- Barrett, Anthony G. M.,Cramp, Susan M.,Roberts, Richard S.,Zecri, Frederic J.
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p. 579 - 582
(2008/02/11)
-
- Process for preparing N-benzyl indoles
-
A process for producing a compound of the formu5la STR1 comprising the step of reacting a compound of the formula STR2 with a compound of the formula STR3 to form a compound of the formula STR4 wherein R2a is selected from the groups recited ab
- -
-
-
- Insecticidal 5-substituted-2,4-diaminopyrimidine derivatives
-
An insecticidal composition comprising, in admixture with an agriculturally acceptable carrier, an insecticidally effective amount of a compound of the formula: STR1 wherein R, R1, R2, R3, R7, R8, m, n, and p are as defined herein, and agriculturally acceptable salts thereof, and methods of using the same.
- -
-
-
- The Wittig reaction of stable ylide with aldehyde under microwave irradiation: Synthesis of ethyl cinnamates
-
The Wittig reaction of stable ylide, triphenyl-carbethoxymethylene phoshorane, with aldehydes was performed within 5-6 minutes under microwave irradiation. Remarkable rate enhancements and dramatic reductions of reaction times have been observed. Thus, the Wittig reaction of stable ylide with aldehyde is optimized.
- Xu,Chen,Fu,Huang
-
p. 2229 - 2233
(2007/10/02)
-