- Palladium Complex Immobilized on Magnetic Nanoparticles Modified with 2-Aminopyridine Ligand: A Novel and Efficient Recoverable Nanocatalyst for C–S and C–Se Coupling Reactions
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A novel, versatile and efficient magnetically recoverable palladium nanocatalyst [Fe3O4@SiO2/2-aminopyridine-Pd(II)] was fabricated via the immobilization of palladium(II) complex on the surface of magnetic nanoparticles modified with 2-aminopyridine ligand. The structure of the as-fabricated Fe3O4@SiO2/2-aminopyridine-Pd(II) nanocomposite was characterized by a series of spectroscopic techniques including FT-IR, SEM, TEM, EDX, TGA, XRD, VSM and ICP-OES techniques. The Fe3O4@SiO2/2-aminopyridine-Pd(II) nanocomposite was utilized under mild and eco-friendly conditions in C–S and C–Se coupling reactions to afford a vast variety of diaryl sulfides and diaryl selenides with good to excellent yields. This heterogeneous palladium catalyst can be magnetically separated and reused for at least 7 consecutive trials without any reduction in activity. Graphical Abstract: [Figure not available: see fulltext.]
- Lu, Lu,Luo, Jia,Wang, Weiqi,Xu, Xiaoqing,Zhang, Jingzheng
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- A magnetically retrievable heterogeneous copper nanocatalyst for the synthesis of 5-substituted tetrazoles and oxidation reactions
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Abstract: A copper complex anchored on functionalized Fe3O4 nanoparticles was prepared by a simple and inexpensive procedure using commercially available materials. The prepared catalyst was characterized by a range of physical and spectroscopic techniques. Ease of operation, high efficiency, eco-friendly procedure, easy separation of the catalyst and reusability for several consecutive runs without significant loss of its activity are several advantages of this catalyst. The catalytic activity has been explored for the oxidation of sulfides, oxidative coupling of thiols and synthesis of 5-substituted tetrazoles. Graphical Abstract: A magnetically retrievable heterogeneous copper nanocatalyst for the synthesis of 5-substituted tetrazoles and oxidation reactions[Figure not available: see fulltext.].
- Darabi, Mitra,Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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p. 703 - 710
(2017/10/07)
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- Zirconium oxide complex-functionalized MCM-41 nanostructure: An efficient and reusable mesoporous catalyst for oxidation of sulfides and oxidative coupling of thiols using hydrogen peroxide
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Zirconium oxide complex-functionalized mesoporous MCM-41 (Zr-oxide@MCM-41) as an efficient and reusable catalyst is reported for the oxidation of sulfides into sulfoxides using hydrogen peroxide (H2O2) as the oxidant, with short reaction times in good to excellent yields at room temperature under solvent-free conditions. Also, a simple and efficient method is reported for the oxidative coupling of thiols into corresponding disulfides in good to high yields using H2O2 as oxidant in the presence of Zr-oxide@MCM-41 as recoverable catalyst in ethanol at room temperature. A series of sulfides and thiols possessing functional groups was successfully converted into corresponding products. After completion of reactions the catalyst was easily separated with simple filtration from the reaction mixture and reused for several consecutive runs without significant loss of catalytic efficiency. The mesoporous catalyst was characterized using Fourier transform infrared spectroscopy, Brunauer-Emmett-Teller surface area measurements, X-ray diffraction, transmission and scanning electron microscopies, energy-dispersive X-ray spectroscopy and thermogravimetric analysis.
- Hajjami, Maryam,Shiri, Lotfi,Jahanbakhshi, Azar
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p. 668 - 673
(2015/09/28)
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- Efficient synthesis of diaryl sulfides by copper-catalysed coupling of aryl halides and thioacetate in water
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A simple economical, and highly efficient catalytic system for the synthesis of diaryl sulfides by a copper-catalysed coupling of aryl halides and thioacetate in water has been developed. A variety of aryl halides reacted with thioacetate to give the desired products in high yields up to 95%. The present catalysis protocol tolerated a wide range of functional groups, including amino, fluoro, and carboxyl moieties.
- Zhang, Yimin,Liu, Li,Chen, Junmin
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- THIOXANTHONE-4-CARBOXYLATES, THEIR PREPARATION METHODS, PHOTOINITIATOR COMPOSITIONS AND USES THEREOF
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The present invention relates to thioxanthone-4-carboxylates, a method for the preparation of the compounds, photoinitiator compositions and use of them as photoinitiators. The compounds of the invention have a structure according to Formula ( I ) below:
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Paragraph 0029; 0030
(2013/05/23)
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- Efficient copper(I)-catalyzed S-arylation of KSCN with aryl halides in PEG-400
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A simple and efficient protocol for CuI-catalyzed C-S bond formation of aryl halides with KSCN to symmetrical diaryl sulfides was reported in PEG-400 without any other additives. A variety of aryl halides were converted to the corresponding diaryl sulfides in good to excellent yields. The present procedure tolerated a variety of functional groups and the steric hindrance of ortho-substituents on aryl halides did not affect the outcome.
- Li, Xiaokang,Yuan, Tangjun,Chen, Junmin
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experimental part
p. 651 - 655
(2012/05/05)
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- Efficient copper-catalyzed double S-arylation of aryl halides with sodium sulfide in PEG-400
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An efficient copper-catalyzed double S-arylation of sodium sulfide with aryl halides in PEG-400 has been developed. With CuI as a catalyst and PEG-400 as a solvent, a range of electron-withdrawing or electron-donating aryl iodides and aryl bromides were found to be applicable to the environmentally benign system. The present procedure is mild and tolerant of a variety of functional groups and the steric hindrance of ortho-substituents on aryl halides did not affect the outcome of good to excellent yields. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Chen, Junmin,Zhang, Yimin,Liu, Li,Yuan, Tangjun,Yi, Fei
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p. 1284 - 1290
(2012/11/07)
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- Antibacterial, antioxidant and binding studies of some novel diaryl sulphide derivatives
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A series of novel acyclic and cyclic diaryl sulphides was synthesized from 2,2-dithiobenzoic acid. The various diaryl sulphides were characterized by use of spectral (IR, 1H and 13C NMR, ESI/MS) and elemental analyses. The antimicrobial activities of the compounds were evaluated in terms of their minimum inhibition concentration (MIC) against a panel of clinical isolates bacteria and were found to possess only moderate antimicrobial activities. N,N-Bis(2-hydroxyphenyl)-2,2-thiodibenzamide (13), exhibiting a hydroxy group at the phenyl ring, was the most active antimicrobial agent within the series, with MIC values of 0.05 mg mL-1 and 10 mg mL -1 against Staphylococcus aureus and Bacillus cereus, respectively. The antioxidant efficiency of the diaryl sulphides was determined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity with 13 being the most active compound. The interaction of 2,2-thiodibenzanilide, N,N-bis(2- methylphenyl)-2,2-thiodibenzamide, and N,N-bis(2-hydroxyphenyl)-2,2- thiobenzamide with guanine, glutamic acid, and urea were studied quantitatively with binding constants ranging from 1 × 103 M1 to 2.7 × 104 M1.
- Moosun, Salma,Bhowon, Minu G.,Jhaumeer-Laulloo, Sabina,Joule, John A.
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p. 1383 - 1400,18
(2020/08/31)
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- Discovery of benzylisothioureas as potent divalent metal transporter 1 (DMT1) inhibitors
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Inhibition of intestinal brush border DMT1 offers a novel therapeutic approach to the prevention and treatment of disorders of iron overload. Several series of diaryl and tricyclic benzylisothiourea compounds as novel and potent DMT1 inhibitors were discovered from the original hit compound 1. These compounds demonstrated in vitro potency against DMT1, desirable cell permeability properties and a dose-dependent inhibition of iron uptake in an acute rat model of iron hyperabsorption. Tricyclic compounds increased the in vitro potency by up to 16-fold versus the original hit. Diaryl compounds 6b and 14a demonstrated significant iron absorption inhibition in vivo with both 25 and 50 mg/kg doses. The diaryl and tricyclic compounds described in this report represent promising structural templates for further optimization.
- Zhang, Zaihui,Kodumuru, Vishnumurthy,Sviridov, Serguei,Liu, Shifeng,Chafeev, Mikhail,Chowdhury, Sultan,Chakka, Nagasree,Sun, Jianyu,Gauthier, Simon J.,Mattice, Maryanne,Ratkay, Laszlo G.,Kwan, Rainbow,Thompson, Jay,Cutts, Alison Brownlie,Fu, Jianmin,Kamboj, Rajender,Goldberg, Y. Paul,Cadieux, Jay A.
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scheme or table
p. 5108 - 5113
(2012/08/28)
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- Rational tuning of the rigidity of a ligand scaffold: synthesis of diphenylsulfide-linked bis(oxazoline) ligands and their application in asymmetric allylic alkylation
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The scaffold rigidity of bis(oxazoline) ligands was rationally tuned on the basis of literature information. Diphenylsulfide-linked bis(oxazoline) ligands with a flexible scaffold were efficiently synthesized to test our hypothesis. The improved enantioselectivity in palladium-catalyzed asymmetric allylic alkylation reaction was achieved as we expected.
- Du, Xian,Liu, Han,Du, Da-Ming
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experimental part
p. 241 - 246
(2010/05/17)
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- BIARYL AND BIHETEROARYL COMPOUNDS USEFUL IN TREATING IRON DISORDERS
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This invention is directed to compounds of formula (I): wherein m, n, R1, R2 and R3 are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment of iron disorders. This invention is also directed to pharmaceutical compositions comprising the compounds and methods of using the compounds to treat iron disorders.
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Page/Page column 43
(2008/12/07)
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- Enzyme-promoted desymmetrization of bis(2-hydroxymethylphenyl) sulfoxide as a route to tridentate chiral catalysts
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The desymmetrization of prochiral bis(2-hydroxymethylphenyl) sulfoxide 3 was efficiently performed via acetylation promoted by commonly available lipases. Two lipases, namely, CAL-B and LPL proved particularly efficient to give 2-acetoxymethylphenyl 2-hydroxymethylphenyl sulfoxide 4 in up to 98% yield and with up to 98% ee. On the basis of an X-ray analysis, the absolute configuration of 4 was determined as (+)-(R). The enantiomerically pure product 4 was then transformed into a series of enantiomerically pure diastereomeric 2-aminomethylphenyl 2-hydroxymethylphenyl sulfoxides 8 in which the amino groups originated from enantiomerically pure amines having additional C-stereogenic centres. Compounds 8 were examined as possible tridentate chiral catalysts in a reference reaction of diethylzinc with benzaldehyde to give the expected product, 1-phenylpropan-1-ol, in moderate yields and with ee's of up to 50%.
- Rachwalski, Michal,Kwiatkowska, Malgorzata,Drabowicz, Jozef,Klos, Marcin,Wieczorek, Wanda M.,Szyrej, Malgorzata,Sieron, Leslaw,Kielbasinski, Piotr
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p. 2096 - 2101
(2008/12/22)
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- 3-Mercaptopropionic Acid: A New Tool in the Synthesis of Symmetrical Diaryl Sulfides from Unactivated Aryl Iodides as Substitute for Anhydrous Sodium Sulfide
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A series of symmetrical diaryl sulfides has been prepared by the copper-catalyzed reaction of 3-mercaptopropionic acid with unactivated aryl iodides.The yields are comparable with those obtained using anhydrous sodium sulfide under optimized reaction conditions.
- Rabai, Jozsef
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p. 523 - 525
(2007/10/02)
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- Synthesis and Properties of Achiral Coronands Incorporating the Sulfide and Sulfoxide Functionality
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A number of polyether coronands incorporating sulfide and sulfoxide functionality and five or six ether oxygen atoms were prepared, their formation of complexes with alkali metal and ammonium salts were studied and the results were compared with analogous
- Raguse, Burkhard,Ridley, Damon D.
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p. 1943 - 1952
(2007/10/02)
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- Synthesis and Conformational Properties of N,N-Dialkyl-6,7-dihydro-5H-dibenzothiazocinium Salts
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N,N-Dialkyl-6,7-dihydro-5H-dibenzothiazocinium salts have been prepared from their corresponding amino alcohols by using p-toluenesulfonyl chloride in acetonitrile.The conformational changes of these quaternary salts were studied by NMR and assi
- Brieaddy, Lawrence E.,Hurlbert, B. Stuart,Mehta, Nariman B.
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p. 1630 - 1634
(2007/10/02)
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- Cyclic sulphur compounds
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Certain tricyclic thioxanthone-10,10-dioxide compounds each of which is substituted in the 1-,2-,3- or 4-position by a carboxyl or (5-tetrazolyl) group and each of which is optionally substituted in the 5-,6-,7- or 8-position by a second carboxyl or (5-tetrazolyl) group or a substituent selected from cyano, halogen, nitro, alkyl, alkoxy, acyl, amino, acylamino, thioalkyl, alkylsulphinyl and alkylsulphonyl, as well as salts, and optionally substituted esters and amides of the carboxyl substituted compounds and alkyl derivatives of the tetrazolyl substituted compounds, are useful for the relief or prophylaxis of allergic conditions.
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- O [(O-piperazinocarbonyl-phenyl)-thio]-benzoates
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Compounds, pharmaceutical preparations containing same, and method of treating depression in mammals, the compounds being of the formula I STR1 or an acid addition salt thereof, particularly a pharmacologically or pharmaceutically acceptable salt thereof,
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