cas 1134-94-7, 2-(Phenylthio)aniline | Articles data

Articles about 1134-94-7Total 51 be found

Article title
Article abstract
Author
Journal number and time
Download

Synthesis and biological evaluation of vanadium complexes as novel anti-tumor agents
A class of vanadium complexes were prepared and investigated for their antiproliferative effects by MTT assay. The structure-activity relationship was extensively studied through the ligand variation. The results showed that the synthetic vanadium complexes demonstrated moderate to good antiproliferative activities against the four cancer cell lines including MGC803, EC109, MCF7 and HepG2, respectively. Of note was that most of the complexes showed preferential growth inhibitory activity to some degree toward gastric cancer line MGC803. Among them, complex 19 exhibited the most and broad-spectrum proliferative inhibition against the tested cell lines. In addition, mechanism studies illustrated that complex 19 could prevent the colony formation, migration and EMT process, as well as induce apoptosis of MGC803 cells. Furthermore, Western blot experiments revealed that the expression of apoptosis-related proteins changed, including up-regulation of Bax, PARP and caspase-3/9, as well as down-regulation of Bcl-2.
Lu, Ling-Pan,Suo, Feng-Zhi,Feng, Ya-Li,Song, Li-Li,Li, Ying,Li, Yang-Jie,Wang, Kai-Ti
p. 1 - 10
(2019)
Read Online

Direct arylation of heterocycles through C-H bond cleavage using metal-organic-framework Cu2(OBA)2(BPY) as an efficient heterogeneous catalyst
A crystalline porous metal-organic-framework Cu2(OBA)2(BPY) was synthesized and characterized by X-ray powder diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), atomic absorption spectrophotometry (AAS), and nitrogen physisorption measurements. The Cu-MOF was shown to be an efficient heterogeneous catalyst for direct C-arylation of a variety of heterocycles by iodoarenes. The optimal conditions employed tBuOLi in dioxane at elevated temperature. In addition, a leaching test was also conducted to investigate the heterogeneity. Gratifyingly, the MOF catalyst can be facilely recycled several times under identical conditions without remarkable loss in catalytic reactivity. This journal is
Truong, Thanh,Nguyen, Vu T.,Le, Hue T. X.,Phan, Nam T. S.
p. 52307 - 52315
(2014)
Read Online

Simple and efficient recyclable catalytic system for performing copper-catalysed S-arylation reactions in the presence of water
A novel protocol for the copper-catalysed S-arylation of thiophenol derivatives with aryl halides leading to diaryl sulfides is reported. The reactions were catalysed by a combination of a copper salt and a 1,2-diamine derivative (acting both as the ligand and as the base) using exclusively water as the solvent. The recovery and successful reutilisation of the aqueous medium containing the active catalyst is described. Furthermore, one example of a "one-pot" process involving Br/I exchange of an aryl bromide and further S-arylation is presented.
Carril, Monica,SanMartin, Raul,Dominguez, Esther,Tellitu, Imanol
p. 5100 - 5105
(2007)
Read Online

Synthesis and antifungal activity of some substituted phenothiazines and related compounds
Several phenothiazines and related compounds were synthesized and their antifungal activity was evaluated in vitro. The results observed for α-chloro-N-acetyl phenothiazine led us to choose this compound as a lead in the search of antifungal agents.
Sarmiento, Gabriela P.,Vitale, Roxana G.,Afeltra, Javier,Moltrasio, Graciela Y.,Moglioni, Albertina G.
p. 101 - 105
(2011)
Read Online

Copper(I) selenophene-2-carboxylate (CuSC) promoted C–S cross-coupling reaction of thiols with aryl iodides
We reported the synthesis of copper (I)-selenophene-2-carboxylate (CuSC) and application as new catalyst in the cross-coupling reactions of thiols with aryl iodide to afford the corresponding unsymmetrical thioethers. The optimized reaction conditions were applied to thiols and aryl iodides having a wide range of functional groups, including electron rich and electron poor substrates. The chemoselectivity of the reaction with 4-iodobromobenzene and 2-aminothiophenol derivatives was briefly examined through the competitive iodine versus bromine and thiol versus nitrogen cross-coupling.
Barros, Olga Soares do Rêgo,Silva, Francielle Rodrigues,Nunes, Vanessa Loren
p. 9 - 17
(2019)
Read Online

Environmentally Friendly and Recyclable CuCl 2-Mediated C-S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent
Simple reaction conditions and recyclable reagents are crucial for environmentally friendly industrial applications. An environment-friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl2-catalyzed C S bondformation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N'-dimethylethane-1,2-diamine (DMEDA) as ligand, base, and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates are compatible and give the corresponding products in good to excellent yields. Both of the reagents in the catalytic system (CuCl2/DMEDA) are inexpensive, conveniently separable, and recyclable for more than five cycles.
Shen, Guodong,Lu, Qichao,Wang, Zeyou,Sun, Weiwei,Zhang, Yalin,Huang, Xianqiang,Sun, Manman,Wang, Zhiming
supporting information
p. 184 - 198
(2021/09/20)

INFLUENZA VIRUS REPLICATION INHIBITOR AND USE THEREOF
Disclosed are a compound as shown in formula (I) as an influenza virus replication inhibitor and a preparation method therefor, a pharmaceutical composition comprising the compound and the use of the compound and pharmaceutical composition thereof in the treatment of influenza.
-
Paragraph 0274-0275

(2020/08/09)

Achieving Nickel Catalyzed C-S Cross-Coupling under Mild Conditions Using Metal-Ligand Cooperativity
A simple and efficient approach of C-S cross-coupling of a wide variety of (hetero)aryl thiols and (hetero)aryl halides under mild conditions, mostly at room temperature, catalyzed by well-defined singlet diradical Ni(II) catalysts bearing redox noninnocent ligands is reported. Taking advantage of ligand centered redox events, the high-energetic Ni(0)/Ni(II) or Ni(I)/Ni(III) redox steps were avoided in the catalytic cycle. The cooperative participation of both nickel and the coordinated ligands during oxidative addition/reductive elimination steps allowed us to perform the catalytic reactions under mild conditions.
Sikari, Rina,Sinha, Suman,Das, Siuli,Saha, Anannya,Chakraborty, Gargi,Mondal, Rakesh,Paul, Nanda D.
p. 4072 - 4085
(2019/04/01)

Design, synthesis and anticancer activity of N-(1-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)-1-oxo-3-phenylpropan-2-yl derivatives
Novel N-(1-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)-1-oxo-3-phenylpropan-2-yl derivatives were designed, synthesized and their chemical structures were confirmed by 1H NMR, 13C NMR and Mass spectra. The anticancer activities of the newly synthesized compounds were evaluated in vitro against three human cancer cell lines including K562, Colo-205 and MDA-MB 231 by MTT assay. The screening results showed that five compounds (16b, 16d, 16i, 16p and 16q) exhibited potent cytotoxic activities with IC50 values between 20 and 40 μM. Further in vitro studies revealed that inhibition of sirtuins could be the possible mechanism of action of these molecules.
Gudisela, Mura Reddy,Srinivasu,Mulakayala, Chaitanya,Bommu, Praveen,Rao, M.V. Basaveswara,Mulakayala, Naveen
p. 4140 - 4145
(2017/08/23)

CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides and Chlorides
We report a general copper-catalyzed cross-coupling of thiols with aryl halides by using N-aryl-N′-alkyl oxalic diamide (L3) or N,N′-dialkyl oxalic diamide (L5) as the ligand. Both aryl and alkyl thiols can be coupled with unactivated aryl bromides and chlorides to give the desired products in good yields. Furthermore, this system features a broad substrate scope and good tolerance of functional groups. Importantly, the oxalic diamides are stable and can be prepared easily from commercially available and cheap starting materials.
Chen, Chia-Wei,Chen, Yi-Ling,Reddy, Daggula Mallikarjuna,Du, Kai,Li, Chao-En,Shih, Bo-Hao,Xue, Yung-Jing,Lee, Chin-Fa
supporting information
p. 10087 - 10091
(2017/08/01)

Discovery of Novel Tricyclic Thiazepine Derivatives as Anti-Drug-Resistant Cancer Agents by Combining Diversity-Oriented Synthesis and Converging Screening Approach
An efficient discovery strategy by combining diversity-oriented synthesis and converging cellular screening is described. By a three-round screening process, we identified novel tricyclic pyrido[2,3-b][1,4]benzothiazepines showing potent inhibitory activity against paclitaxel-resistant cell line H460TaxR (EC50 50 > 100 μM against normal human fibroblasts). The most active hits also exhibited drug-like properties suitable for further preclinical research. This redeployment of antidepressing compounds for anticancer applications provides promising future prospects for treating drug-resistant tumors with fewer side effects.
Xiang, Jinbao,Zhang, Zhuoqi,Mu, Yan,Xu, Xianxiu,Guo, Sigen,Liu, Yongjin,Russo, Daniel P.,Zhu, Hao,Yan, Bing,Bai, Xu
p. 230 - 235
(2016/06/01)

Catalytic hydrogenation of sulfur-containing nitrobenzene over Pd/C catalysts: In situ sulfidation of Pd/C for the preparation of PdxSy catalysts
The preparation of supported palladium sulfides catalysts has attracted much attention due to their good sulfur-resistant properties in the hydrogenation of sulfur-containing compounds. In this work, we unambiguously demonstrated that Pd/C catalyst could be in situ sulfided by organic sulfur-containing reactant molecules and the sulfidation was highly dependent on temperature. The in situ sulfidation of Pd/C catalyst was composed of a reaction of Pd with the sulfur derived from the cleavage of C-S bond of sulfur-containing reactant molecules, followed by a transformation to PdxSy at high temperatures (around 120 °C). The sulfided Pd/C catalyst could be used for at least 18 recycles without a significant loss in its activity during the hydrogenation of sulfur-containing nitrobenzene at 180 °C with 3 MPa H2, which could be attributed to the stable presence of Pd4S and Pd16S7.
Zhang, Qunfeng,Xu, Wei,Li, Xiaonian,Jiang, Dahao,Xiang, Yizhi,Wang, Jianguo,Cen, Jie,Romano, Stephen,Ni, Jun
p. 17 - 21
(2015/09/28)

Copper nanopowder catalyzed cross-coupling of diaryl disulfides with aryl iodides in PEG-400
An eco-friendly thiolation via diaryl disulfides and aryl iodides under ligand-free conditions is reported. With copper nanopowder as catalyst and PEG-400 as solvent, a variety of unsymmetrical diaryl sulfides are synthesized in good to excellent yields. The process is free from foul-smelling and unstable thiols and the copper nanopowder-PEG-400 catalytic system can be directly reused for four repetitive cycles.
Wu, Xiang-Mei,Yan, Guo-Bing
supporting information
p. 537 - 542
(2015/04/27)

Synthesis and characterization of titanium complexes bearing sulfoxide groups and their catalytic behaviors in ethylene homo- and copolymerization
Titanium complexes derived from 2,4-di-tert-butyl-6-((2-(arylsulfinyl) phenylimino)methyl)phenol are designed and synthesized. X-ray diffraction studies reveal that the complexes adopt distorted octahedral geometry with O(phenol), N(imine), and O(sulfoxide) coordinated with titanium. Combined with modified methylaluminoxane(MMAO), the complexes exhibit moderate to high activity to afford polyethylene even at 120 °C under 1 atm ethylene pressure. The complexes also show excellent capability in copolymerization of ethylene with either 1-hexene or norbornene. Results indicate that the introduction of sulfoxide groups could open the space around central metal and favors the insertion of bulky comonomers.
Wang, Zheng,Peng, Ai-Qing,Sun, Xiu-Li,Tang, Yong
p. 1144 - 1149
(2014/08/18)

A convenient and efficient copper-catalyzed synthesis of unsymmetrical and symmetrical diaryl chalcogenides from arylboronic acids in ethanol at room temperature
A simple and convenient approach for the synthesis of unsymmetrical diaryl chalcogenides (Te, Se, and S) has been developed by copper-catalyzed cross-coupling reaction of organoboronic acid with diaryl dichalcogenide in ethanol using NaBH4 in air or oxygen. The present methodology is highly practical for the synthesis of unsymmetrical diaryl tellurides with various functionalities such as -NO2, -F, -Br, and -COOH that have been obtained in good to excellent yields. Methodology is also effective for the synthesis of unsymmetrical diaryl selenides and sulfides. Moreover, symmetrical diaryl selenides have also been obtained from arylboronic acids using elemental selenium powder under optimized reaction conditions. The use of NaBH 4 is the key for the development of milder reaction conditions, which enable the construction of unsymmetrical diaryl chalcogenides from boronic acid substrates in ethanol at room temperature.
Kumar, Amit,Kumar, Sangit
p. 1763 - 1772
(2014/03/21)

Iron-catalyzed S-arylation of benzothiazole with aryl iodides under aqueous medium: Facile synthesis of aryl(2-aminoaryl) sulfides
A simple route for facile access of aryl(2-aminoaryl) sulfide was reported. With the aid of iron(III) chloride catalyst and diamine ligand, benzothiazole was efficiently S-arylated with various aryl iodides (19 examples) in water under air atmosphere. This operationally simple protocol provides aryl(2-aminoaryl) sulfides in moderate to good yields.
Lee, Hang Wai,Yung, Ka Fu,Kwong, Fuk Yee
supporting information
p. 2743 - 2747
(2015/01/08)

Iron-Catalyzed S-Arylation of Benzothiazole with Aryl Iodides under Aqueous Medium: Facile Synthesis of Aryl(2-aminoaryl) Sulfides
A simple route for facile access of aryl(2-aminoaryl) sulfide was reported. With the aid of iron(III) chloride catalyst and diamine ligand, benzothiazole was efficiently S-arylated with various aryl iodides (19 examples) in water under air atmosphere. This operationally simple protocol provides aryl(2-aminoaryl) sulfides in moderate to good yields.
Lee, Hang Wai,Yung, Ka Fu,Kwong, Fuk Yee
supporting information
p. 2743 - 2747
(2015/05/05)

Efficient C-S cross-coupling of thiols with aryl iodides catalyzed by Cu(OAc)2·H2O and 2,2′-biimidazole
The classical Ullmann C-S cross coupling reaction of aryl iodides with aromatic/alkyl thiols under catalysis of 15 mol% Cu(OAc)2· H2O and 15 mol% 2,2′-biimidazole works at 80°C in DMSO for 3 h to provide a variety of aryl sulfides in good to excellent yields. The classical Ullmann C-S cross coupling reaction of aryl iodides with aromatic/alkyl thiols under catalysis of 15 mol% Cu(OAc)2· H2O and 15 mol% 2,2′-biimidazole works at 80°C in DMSO for 3 h to provide a variety of aryl sulfides in good to excellent yields. Copyright
Zong, Chenglong,Liu, Jianli,Chen, Shengyan,Zeng, Runsheng,Zou, Jianping
supporting information
p. 212 - 218
(2014/04/03)

Synthesis, characterization and antimicrobial activity of 2-(11-oxodibenzo [b,f][1,4]thiazepin-10(11H)-yl)-N (substituted phenyl) acetamide derivatives
Substituted dibenzo [b,f][1,4]thiazepines analogues carrying 2-chloro N-phenylacetamide moiety attached to 11-C position have been synthesized and evaluated using IR, 1H NMR and mass spectra. Antibacterial properties have been examined for the synthesized derivatives against gram positive and gram negative bacteria. 2-(11-Oxodibenzo [b,f][1,4]thiazepin-10(11H)-yl)-N phenylacetamide derivatives show good significant antimicrobial activity.
Tailor, Jitesh H.,Patel, Priti C.,Malik
p. 1263 - 1268
(2014/12/10)

Diversified synthesis of novel quinoline and dibenzo thiazepine derivatives using known active intermediates
The novel drug development to control resisting infections in conventional drug therapy is a need of today. Few antiulcer relative derivatives developed by approaching convergent synthesis. The derivatives synthesized successfully are dibenzo thiazepine-pyridine (SLN11-SLN15) and benzimidazole-hydroquinoline based derivatives (SLN16-SLN20). It involved the coupling through microwave, sonication and conventional techniques at final step. The efficient technology identified as sonication technique basically time and yield. The reported compounds were structural characterized by elemental analysis and spectral studies such as 1H, 13C NMR and MS.
Sharada,Satyanarayana Reddy,Sammaiah,Sumalatha
p. 7959 - 7966
(2013/09/23)

Potassium tert-butoxide-mediated synthesis of unsymmetrical diaryl ethers, sulfides and selenides from aryl bromides
Potassium tert-butoxide mediated carbon-chalcogen C-E (E=O, S and Se) coupling reaction has been studied from aryl bromide and phenol/aryl disulfide/diselenide substrates. A series of unsymmetrical diaryl chalcogenides were accessed from aryl bromide and diaryl dichalcogenide precursors by using 2.5 equiv of potassium tert-butoxide in DMSO at 80 C. Unsymmetrical diaryl ethers were also obtained by using phenol precursors at 40-45 C. Aryl bromides with methyl, trifluoromethyl, methoxy and nitro substituents showed compatibility in the carbon-chalcogen bond forming reaction. 4-Methoxy, methyl, trifluoromethyl substituted bromobenzene substrates gave two regioisomers: 3-substituted and 4-substituted diaryl chalcogenides when reacted with phenols/diaryl disulfides/diselenides. Formation of two regioisomeric diaryl chalcogenides in the reaction mixture suggests that potassium tert-butoxide reacts with bromobenzene to produce benzyne intermediate, which subsequently reacts with diaryl dichalcogenides and finally give a regioisomeric mixture of 4-substituted and 3-substituted diaryl chalcogenides.
Kumar, Amit,Bhakuni, Bhagat Singh,Prasad, Ch. Durga,Kumar, Shailesh,Kumar, Sangit
p. 5383 - 5392
(2013/07/04)

Mechanistic exploration of the palladium-catalyzed process for the synthesis of benzoxazoles and benzothiazoles
A convenient one-pot palladium-catalyzed cascade process for the preparation of both benzoxazoles and benzothiazoles has been developed. While these reactions proceed to give similar compounds the mechanisms governing the processes are different as are the experimental conditions employed.
Bochatay, Valentin N.,Boissarie, Patrick J.,Murphy, John A.,Suckling, Colin J.,Lang, Stuart
p. 1471 - 1477
(2013/03/28)

Cu-grafted mesoporous organic polymer: A new recyclable nanocatalyst for multi-component, N-arylation and S-arylation reactions
A new mesoporous Cu-MPTA-1 nanocatalyst has been synthesized via a simple and facile in situ radical polymerization of triallylamine in the presence of an organic-organic self-assembly of anionic surfactant SDS, followed by grafting of Cu(ii) at room temperature under an inert atmosphere. This nanomaterial has been characterized by elemental analysis, powder X-ray diffraction (XRD), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), UV-vis diffuse reflectance spectroscopy (DRS), thermogravimetric analysis (TGA), N2 adsorption-desorption studies, X-ray photoelectron spectroscopy (XPS) and EPR spectroscopy. Cu-MPTA-1 acts as an efficient heterogeneous nanocatalyst exhibiting a high catalytic activity for N-arylation and S-arylation reactions using water as a green solvent and also exhibits an excellent catalytic activity for the one-pot synthesis of propargylamines via a three component coupling of an alkyne, an amine and an aldehyde at room temperature. Moreover, the catalyst is easily recoverable and can be reused six times without an appreciable loss of catalytic activity in the three component coupling reaction. The highly dispersed Cu(ii) sites in the Cu-grafted mesoporous polymer could be responsible for the observed high activities of the Cu-MPTA-1 catalyst in the coupling reactions. No evidence of leached Cu from the catalyst during the course of the reaction has been observed, suggesting true heterogeneity in the catalytic process. The Royal Society of Chemistry.
Salam, Noor,Kundu, Sudipta K.,Roy, Anupam Singha,Mondal, Paramita,Roy, Susmita,Bhaumik, Asim,Islam, Sk. Manirul
p. 3303 - 3316
(2013/12/04)

A new family of nucleophiles for photoinduced, copper-catalyzed cross-couplings via single-electron transfer: Reactions of thiols with aryl halides under mild conditions (O C)
Building on the known photophysical properties of well-defined copper-carbazolide complexes, we have recently described photoinduced, copper-catalyzed N-arylations and N-alkylations of carbazoles. Until now, there have been no examples of the use of other families of heteroatom nucleophiles in such photoinduced processes. Herein, we report a versatile photoinduced, copper-catalyzed method for coupling aryl thiols with aryl halides, wherein a single set of reaction conditions, using inexpensive CuI as a precatalyst without the need for an added ligand, is effective for a wide range of coupling partners. As far as we are aware, copper-catalyzed C-S cross-couplings at 0 C have not previously been achieved, which renders our observation of efficient reaction of an unactivated aryl iodide at -40 C especially striking. Mechanistic investigations are consistent with these photoinduced C-S cross-couplings following a SET/radical pathway for C-X bond cleavage (via a Cu(I)-thiolate), which contrasts with nonphotoinduced, copper-catalyzed processes wherein a concerted mechanism is believed to occur.
Uyeda, Christopher,Tan, Yichen,Fu, Gregory C.,Peters, Jonas C.
supporting information
p. 9548 - 9552
(2013/07/19)

Exploration of the structure-activity relationship of the diaryl anilide class of ligands for translocator protein - Potential novel positron emitting tomography imaging agents
A series of novel ligands based on the diaryl anilide (DAA) class of translocator protein (TSPO) ligands was synthesised and evaluated as potential positron emitting tomography (PET) ligands for imaging TPSO in vivo. Fluorine-18 labelling of the molecules was achieved using direct radiolabelling or synthon based labelling approaches. Several of the ligands prepared have promising profiles as potential TSPO PET imaging ligands and will be evaluated further as potential clinical imaging agents.
Wadsworth, Harry,Jones, Paul A.,Chau, Wai-Fung,Durrant, Clare,Morisson-Iveson, Veronique,Passmore, Joanna,O'Shea, Dennis,Wynn, Duncan,Khan, Imtiaz,Black, Andrew,Avory, Michelle,Trigg, William
p. 5795 - 5800,6
(2020/07/30)

Unexpectedly ligand-free copper-catalyzed C-S cross-coupling of benzothiazole with aryl iodides in aqueous solution
A novel synthetic protocol for 2-aminophenyl sulfide derivatives via the reactions of benzothiazole with aryl iodides was reported for the first time. The reactions were catalyzed by CuCl with tetrabutylammonium hydroxide as the base and water as the solvent without ligand at 50°C or room temperature. A variety of aryl iodides underwent the C-S cross-coupling reaction with benzothiazole to afford smoothly the corresponding products in excellent yield.
Feng, Yi-Si,Qi, Hong-Xia,Wang, Wei-Cheng,Liang, Yu-Feng,Xu, Hua-Jian
supporting information; experimental part
p. 2914 - 2917
(2012/07/27)

Copper powder catalyzed direct ring-opening arylation of benzazoles with aryl iodides in polyethylene glycol
The expedient and efficient copper powder catalyzed direct ring-opening arylation of benzazoles with aryl iodides in polyethylene glycol that proceeds in the absence of an added ligand has been developed. The protocol provides facile access to 2-(arylthio)anilines and 2-phenoxyanilines in high yields with a wide tolerance of functional groups. Transmission electron microscopy confirmed that the active catalyst results from the in situ generation of copper nanoparticles under standard reaction conditions, which is an alternative avenue to develop a highly effective metallic copper catalyst. Moreover, the catalytic system can be recycled up to six times. Copyright
Yao, Lifang,Zhou, Qing,Han, Wei,Wei, Shaohua
supporting information
p. 6856 - 6860
(2013/02/22)

Heterogeneous magnetic catalyst for S-arylation reactions
A convenient method for the synthesis of monodisperse, superparamagnetic copper ferrite (CuFe2O4) nanoparticles with high surface area has been described. The synthesized material was characterized by various techniques. XRD showed the nanocrystalline nature of CuFe2O 4 with a crystallite size of 6 nm. TEM analysis showed that uniform spherical CuFe2O4 particles are formed with a size of 55 ± 5 nm. N2 adsorption/desorption measurements confirmed the mesoporous nature of the sample with surface area >216 m2 g -1. The field dependent magnetization, illustrated by VSM and saturation magnetization was found to be 44 emu g-1. The catalytic applications of the synthesized CuFe2O4 nanoparticles were explored for the cross-coupling of thiols with diverse range of aryl halides. Aryl iodides and bromides result in biarylsulfides in good to excellent yields (62-98%) whereas aryl chlorides gave significant amount of diaryldisulfide. Scope of this catalytic protocol further extended to one-pot synthesis of biologically important tricyclic dibenzothiazepines. The superparamagnetic nature of CuFe2O4 nanoparticles was found to be advantageous for their easy, quick and quantitative separation from the reaction mixture. Negligible leaching of Cu and Fe in consecutive cycles makes the catalyst economical and environmentally benign.
Panda, Niranjan,Jena, Ashis Kumar,Mohapatra, Sasmita
experimental part
p. 258 - 264
(2012/08/28)

8-hydroxyquinolin-N-oxide-promoted copper-catalyzed C-S cross-coupling of thiols with aryl iodides
8-Hydroxyquinolin-N-oxide was identified as a superior ligand for CuI-catalyzed C-S coupling reactions of aryl iodides with thiols to afford the corresponding thioethers in excellent yield. The method shows excellent chemoselectivity and high functional-group tolerance in both coupling partners. Copyright
Su, Kun,Qiu, Yatao,Yao, Yiwu,Zhang, Dayong,Jiang, Sheng
supporting information
p. 2853 - 2857
(2013/02/21)

Synthesis and antibacterial activities of new dibenzothiazepine derivatives
A number of substituted dibenzo[b,f][1,4]thiazepines analogues carrying heterocyclic and aliphatic moiety attached to C-11 position have been synthesized and evaluated their antibacterial activities against gram positive and gram negative bacteria. Derivatives of imidazole, 2-methyl imidazole and pyrrolidine exhibit significant antibacterial activities.
Mahale, Ganesh D.,Kolekar, Yogesh M.,Kumar, Ashok,Singh, Dharmendra,Kodam, Kisan M.,Waghmode, Suresh B.
scheme or table
p. 1196 - 1201
(2011/10/12)

FeF3/i2-catalyzed synthesis of 4-chalcogen- substituted arylamines by direct thiolation of an arene C-H bond
An efficient regioselective synthesis of 4-chalcogen-substituted-arylamines by FeF3-catalyzed sulfenylation and selenation of arylamines has been developed. In the presence of FeF3and I2, a variety of arylamines underwent the reaction with disulfides or diselenides to afford the corresponding 4-sulfenyl-or 4-selenenyl-arylamines in moderate to good yields. Georg Thieme Verlag Stuttgart.
Fang, Xiao-Li,Tang, Ri-Yuan,Zhang, Xing-Guo,Li, Jin-Heng
experimental part
p. 1099 - 1105
(2011/05/14)

Oxidoreductive coupling of thiols with aryl halides catalyzed by copper on iron
Synthesis and utilization of a simple copper on iron catalyst in the coupling of aryl halides with thiols through disulfide intermediate is reported. The iron support of copper catalyst ensures reductive media for the coupling, allows easy removal of the metals by outer magnetic field and enables the recycling of the catalyst.
Kovacs, Szabolcs,Novak, Zoltan
experimental part
p. 711 - 716
(2011/03/22)

An efficient copper-catalyzed cross-coupling reaction of thiols with aryl iodides
Commercially available Cu2O powder is a very reactive catalyst for the coupling of thiols to aryl iodides. A variety of functional groups including esters, unprotected amines, alcohols, and heterocycles tolerate the reaction conditions. Moreover, di-ortho-substituted aryl iodides with sterically demanding substrates were also coupled to give the desired aryl thioethers in good to excellent yields. Copyright
Kao, Hsin-Lun,Chen, Chin-Keng,Wang, Yu-Jen,Lee, Chin-Fa
experimental part
p. 1776 - 1781
(2011/05/03)

Synthesis of azido arylselenides and azido aryldiselenides: a new class of selenium-nitrogen compounds
We present here our results of the efficient synthesis of azido arylselenides and azido aryldiselenides under mild conditions. Starting from nitrogen-substituted benzenes, we incorporated selenium atom at aromatic ring and obtained amino arylselenides and diselenides in satisfactory yields. Treatment of these compounds with iso-pentyl nitrite (i-C5H11ONO) and azido trimethylsilane (Me3SiN3) in THF affords a variety of azido arylselenides and diselenides in good to excellent yields.
Deobald, Anna Maria,Simon de Camargo, Leandro R.,Tabarelli, Greice,H?rner, Manfredo,Rodrigues, Oscar E.D.,Alves, Diego,Braga, Ant?nio L.
experimental part
p. 3364 - 3367
(2010/08/19)

Solvent-free copper-catalyzed oxidative S-arylation of 1,2-diaryldisulfides with aryltrimethoxysilane
A novel and solvent-free protocol for the synthesis of diarylsulfides by the copper-catalyzed oxidative S-arylation of 1,2-diaryldisulfides with aryltrimethoxysilanes is reported. In the presence of CuI, 2-(di-tert-butylphosphino)biphenyl, and TBAF (n-Bu
Luo, Pei-Song,Yu, Ming,Tang, Ri-Yuan,Zhong, Ping,Li, Jin-Heng
supporting information; scheme or table
p. 1066 - 1070
(2009/05/11)

A highly efficient and widely functional-group-tolerant catalyst system for copper(I)-catalyzed S-arylation of thiols with aryl halides
A mild, general, and efficient copper-catalyzed system for C-S bond formation with high chemoselectivity and wide functional group tolerance is developed. With CuBr as catalyst and 1,2,3,4-tetrahydro-8-hydroxy-quinoline as ligand, the S-arylation of thiols with aryl halides performed well, the activated aryl iodides could take place even at room temperature, and the activated aryl bromides and chlorides give the corresponding products with good to excellent yields as well.
Feng, Yang,Wang, Huifeng,Sun, Fangfang,Li, Yaming,Fu, Xinmei,Jin, Kun
supporting information; experimental part
p. 9737 - 9741
(2010/02/27)

Efficient C-S cross coupling catalyzed by Cu2O
A protocol for the copper-catalyzed C-S bond formation between aryl, alkyl, or heteroaryl thiols and aryl or heteroaryl halides is reported. The reaction is catalyzed by Cu2O which shows the highest catalytic activity with ethyl 2-oxocyclohexanecarboxylate ligand in DMSO at 80 °C. The corresponding coupling products are obtained with good to excellent yields under relatively mild reaction conditions with good chemoselectivity and functional group tolerance.
Xu, Hua-Jian,Zhao, Xiao-Yang,Deng, Jin,Fu, Yao,Feng, Yi-Si
experimental part
p. 434 - 437
(2009/05/11)

Ligand-free C-S bond formation catalyzed by copper(I) oxide
An efficient ligand-free Cu2O-catalyzed C-S bond-formation reaction was developed. A large number of diaryl sulfides and alkylaryl sulfides could be rapidly assembled using this new reaction protocol. Georg Thieme Verlag Stuttgart.
Xu, Hua-Jian,Zhao, Xiao-Yang,Fu, Yao,Feng, Yi-Si
experimental part
p. 3063 - 3067
(2009/07/04)

Ligand-free copper-catalyzed C-S coupling of aryl iodides and thiols
(Chemical Equation Presented) A protocol for the copper-catalyzed aryl-sulfur bond formation between aryl iodides and thiophenols is reported. The reaction is catalyzed by a low amount (1-2.5 mol %) of readily available and ligand-free copper iodide salt. A variety of diaryl thioethers are synthesized under relatively mild reaction conditions with good chemoselectivity and functional group tolerance.
Sperotto, Elena,Van Klink, Gerard P. M.,De Vries, Johannes G.,Van Koten, Gerard
p. 5625 - 5628
(2008/12/21)

PROCESS FOR THE PREPARATION OF 11-(1-PIPERAZINYL)DIBENZO `B, F! `1 ,4!-THIAZEPINE, AN INTERMEDIATE IN THE SYNTHESIS OF THE ANTIPSYCHOTIC DRUG QUETIAPINE
A process for the preparation of 11-(1-piperazinyl)dibenzo-[b, f ] [ 1, 4 ] thiazepine comprising reacting phenyl 2-(phenylthio) phenylcarbamate with piperazine and cyclizing the obtained N-[ (2 -phenylthio) phenyl ] -1 -piperazinylcarboxamide in a presence of cyclizing agent. 11-(1-piperazinyl)-dibenzo [b, f] [1, 4]thiazepine is itself, an intermediate in the synthesis of antipsychotic drug Quetiapine.
-
Page/Page column 6-8

(2008/06/13)

N-acylsulfonamide apoptosis promoters
N-Benzoyl arylsulfonamides having the formula are BCL-Xl inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-Xl inhibiting compositions and methods of promoting apoptosis in a mammal.
-
(2008/06/13)

N-Acylsulfonamide apoptosis promoters
N-Benzoyl arylsulfonamides having the formula Are BCL-X1 inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-X1 inhibiting compositions and methods of promoting apoptosis in a mammal.
-
(2008/06/13)

Synthesis and antitumor activity of some new substituted quinolin-4- one and 1,7-naphthyridin-4-one analogs
The synthesis of some new analogs of quinolin-4-one and 1,7- naphthyridin-4-one is described. The prepared compounds were tested for their in vitro antitumor and cdc2 kinase or cdc25 phosphatase inhibitory activity. Compound ethyl 7-oxo-2,3-dihydro-7H-pyrido [1,2,3-de][2,3- b]pyrido-1,4-thiazine-6-carboxylate (6b) showed antitumor activity against CNS SNB-75, breast T-47D, and lung NCI-H522 cancer cell lines with GI50 values of 8.3, 17.6, and 22.7 μM, respectively. Meanwhile, the compounds ethyl 4-oxo-8-phenylthio-1H,4H-quinoline-3-carboxylate (11a) and 4-oxo-8- phenylthio-1H,4H-1,7-naphthyridine-3-carboxylic acid (12b) have proved to be cdc25 phosphatase inhibitors at IC50 values of 11 and 5 μM, respectively.
El-Subbagh,Abadi,Al-Khawad,Al-Rashood
p. 19 - 24
(2007/10/03)

1H and 13C NMR Study of Substituted Effects in 2- and 3-Substituted Diphenyl Sulphides and Sulphones and 4-Substituted 2',6'-Dimethyldiphenyl Sulphides
The proton and carbon NMR spectra of nine 2-substituted diphenyl sulphides (S-2-X), seven 3-substituted diphenyl sulphides (S-3-X), nine 2-substituted diphenyl sulphones (SO2-2-X), nine 3-substituted diphenyl sulphones (SO2-3-X) and nine 4-substituted-2',6'-dimethyldiphenyl sulphides (Me2-S-4-X) were obtained.Correlations of the 1H and 13C chemical shifts were made with benzene substituent-induced chemical shifts (Lynch plots) and Hammett and dual-substituent parameters and the results were compared with those of 4-substituted diphenyl sulphides (S-4-X) and sulphones (SO2-4-X).The main conclusions are as follows: (i) the transmission of the substituent effects in substituted diphenyl sulphides decreases in the order S-4-X ca.S-2-X > Me2-S-4-X > S-3-X; (ii) the inductive effects are transmitted to a larger extent than the resonance effects to the unsubstituted ring in 3-substituted diphenyl sulphides, while the reverse trend is observed in other substituted diphenyl sulphides; (iii) in 2-methoxy-, 2-chloro-, 2-bromo- and 2-nitrodiphenyl sulphides, an increase in the size of the substituent causes an upfield shift for H-6 ascribable to the repulsion between the lone pairs of electrons on the sulphur and the substituent and its influence on the conformation; (iv) the diminished transmission of substituent effects to the remote rings in 4-substituted 2',6'-dimethyldiphenyl sulphides is probably due to the orthogonal orientation of the rings; and (v) the signal due to the H-6 of 2-substituted diphenyl sulphones suffers a downfield shift with an increase in the size of the substituent, this being ascribable to the increasing steric interaction between the 2-substituent and the sulphonyl oxygen and consequent changes in the conformation. - Keywords: NMR; 1H NMR; 13C NMR; diphenyl sulphides; diphenyl sulphones; ?-polarization
Perumal, Subbu,Chandrasekaran, Ramasubbu,Vijayabaskar, Veerappan,Wilson, David A.
p. 779 - 790
(2007/10/03)

Aromatic nucleophilic polysubstitution by sequential SRN1 reactions
Substitution of aromatics (benzene, naphthalene and pyridine) by two or three distinct nucleophiles derived from phosphonates and/or thiolates can be performed by sequential photosimulated SRN1 reactions whose radical chain mechanism is compatible with the successively introduced substituents. aromatic polysubstitution / SRN1 mechanism / disubstituted aromatic / trisubstituted aromatic / distinct substituent
Beugelmans, Rene,Chbani, Mohamed
p. 290 - 305
(2007/10/02)

NEW HETEROCYCLIC SYNTHESES FROM α-HALOHYDRAZONES. REARRANGEMENTS OF α-ARYLAMINO- AND α-ARYLTHIOACYLHYDRAZONES IN ACID MEDIUM
α-(Arylamino)-acylhydrazones 1d-f react with polyphosphoric acid to give 2-arylazoindoles 3a-d through a cyclodehydration process involving the arylamino moiety.A deviation from the expected course is observed with the aldehydic substrates 1a-c which give the isatine derivatives 2a-c. α-(Arylthio)-acylhydrazones 1g-i give the 3-(arylthio)cinnolines 4b-d and 4-aminophenyl phenylsulphide 5, the latter being formed through an unprecedented rearrangement.A similar rearrangement is shown by α-phenylthio-α-phenylhydrazonobenzaldehyde, 6, which give 2-aminophenyl phenyl sulphide, 7.
Benincori, Tiziana,Fusco, Raffaello,Sannicolo, Franco
p. 635 - 639
(2007/10/02)

SULFENAMIDES AND SULFINAMIDES IV. HOMOLYSIS OF SULFENAMIDES IN CYCLOHEXENE
The photocatalysed decomposition of aromatic sulfenamides in cyclohexene is a rapid reaction at ambient temperature.Products fall into two main groups resulting from recombination of initially formed radicals and from intervention of solvent acting as a radical trap.Key words: Aromatic sulfenamides; photolysis; homolysis; free-radicals
Chan, Christopher L. K.,Duffield, Alan M.,Cole, Edward R.,Southwell-Keely, Peter T.
p. 199 - 206
(2007/10/02)

Reaction of Phenylnitrenium Ion with Sulphides. A Novel Synthetic Method for Aminophenyl Sulphide Derivatives
The reaction of phenyl azide with sulphides in the presence of both trifluoroacetic acid and trifluoromethanesulphonic acid to produce 2- and 4-aminophenyl sulphides (2) and (3) was investigated in order to obtain information on the following points: the kinetics of decomposition of phenyl azide, the effect of addition of benzene to reaction systems, the replacement of phenyl azide by 1-phenyl-2-methyl-4,6-diphenylpyridinium salt, and the steric and electronic effect of substituents in the sulphides.The products are formed through an azasulphonium ion by reaction of phenylnitrenium ion with sulphide, followed by rearrangement of the alkyl group in the azasulphonium ion.Sulphides with primary alykl groups larger than propyl result in selective formation of ortho-products (2), the mechanism of which is discussed in detail.
Takeuchi, Hiroshi,Hirayama, Shinji,Mitani, Michiharu,Koyama, Kikuhiko
p. 521 - 528
(2007/10/02)

THERMAL REACTIVITY OF 4'SUBSTITUTED- AND 4'-SUBSTITUTED-2-PHENYL-BENZENESUPHENANILIDES
The thermal decomposition of 4'-nitro, 4'-H, and 4'-methoxy-benzenesulphenanilides in benzene and/or furan, and of 4'-substituted-2-phenylbenzenesulphenanilides ( 1d-1f ) in benzene, was found to proceed by two distinct pathways: ( i ) nucleophilic displacement by furan and/or another sulphenanilide unit and ( ii ) homolytic S-N bond fission to give sulphenyl and anilino radicals.An increase in the electron-withdrawning capability of the 4'-substituted favours the ionic pathway, whwreas the radical pathway is favoured by an increase in the reaction temperature.
Benati, Luisa,Montevecchi, Pier Carlo,Spagnolo, Piero
p. 99 - 104
(2007/10/02)