- Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment
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Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.
- Chai, Jianqi,Chen, Min,Jin, Fei,Kong, Xiangyi,Wang, Xiaobin,Xue, Wei,Yang, Chunlong
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- Rhodium-catalyzed Sommelet-Hauser type rearrangement of α-diazoimines: Synthesis of functionalized enamides
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An efficient rhodium catalyzed Sommelet-Hauser type rearrangement of sulfur ylides derived from α-thioesters and N-sulfonyl-1,2,3-triazoles has been successfully accomplished for the synthesis of various functionalized enamides. The developed reaction involves the unprecedented [2,3]-sigmatropic rearrangement of sulfur ylides with the imine motif. Importantly, the method works well with various substituted α-thioesters/-amides/-ketones and substituted N-sulfonyl-1,2,3-triazoles and allows the synthesis of diverse enamide derivatives in good to excellent yields. The reaction was also successfully extended to the one-pot synthesis of enamides from terminal alkynes.
- Anbarasan, Pazhamalai,Ramachandran, Kuppan,Reddy, Angula Chandra Shekar,Reddy, Palagulla Maheswar
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supporting information
p. 5649 - 5652
(2020/06/09)
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- Design, synthesis and bioactivity evaluation of novel thioether derivatives containing a sulfonohydrazide moiety
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A series of novel thioether derivatives containing a sulfonohydrazide moiety were synthesized and determined using 1H NMR, 13C NMR, HRMS, and elemental analysis. Their in vitro antibacterial activities against Xanthomonas oryzae pv.
- Li, Pei,Zhou, Junliang,Liu, Yan,Wang, Xiang
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p. 976 - 980
(2020/07/03)
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- Synthesis and biological evaluation of 2-(4-substituted benzene-1-sulfonyl)-N'-(substituted-1-sulfonyl)acetohydrazide as antibacterial agents
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In this study, a series of new sulfone derivatives containing a sulfonohydrazide moiety were synthesized and their structures were determined using 1H NMR, 13C NMR, and HRMS. Then, the in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac) were evaluated by performing turbidimeter test. Bioactivity results showed that compound 2-(4-fluorobenzene-1-sulfonyl)-N′-(4-fluorobenzene-1-sulfonyl)acetohydrazide (5g) revealed the best antibacterial activities against Xoo and Xac, with the 50percent effective concentration (EC50) values of 25 and 36?μg/mL, respectively, which were superior to those of thiodiazole copper (110 and 230?μg/mL, respectively) and bismerthiazol (84 and 146?μg/mL, respectively).
- Li, Pei,Zhou, Junliang,Liu, Yan,Wang, Xiang
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p. 4559 - 4565
(2020/07/10)
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- Air-stable binuclear Titanium(IV) salophen perfluorobutanesulfonate with zinc power catalytic system and its application to C–S and C–Se bond formation
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An air-stable μ-oxo-bridged binuclear Lewis acid of titanium(IV) salophen perfluorobutanesulfonate [{Ti(salophen)H2O}2O][OSO2C4F9]2 (1) was successfully synthesized by the reaction of TiIV(salophen)Cl2 with AgOSO2C4F9 and characterized by techniques such as IR, NMR and HRMS. This complex was stable open to air over a year, and exhibited good thermal stability and high solubility in polar organic solvents. The complex also had relatively strong acidity with a strength of 0.8 Ho ≤ 3.3, and showed high catalytic efficiency towards various C–S and C–Se bond formations in the presence of zinc power. This catalytic system affords a mild and efficient approach to synthesis of thio- and selenoesters, α-arylthio- and seleno-carbonyl compounds, and thio- and selenoethers.
- Wang, Lingxiao,Qiao, Jie,Wei, Jiancong,Liang, Zhiwu,Xu, Xinhua,Li, Ningbo
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- Modular Synthesis of Carbon-Substituted Furoxans via Radical Addition Pathway. Useful Tool for Transformation of Aliphatic Carboxylic Acids Based on "build-and-Scrap" Strategy
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Utilizing radical chemistry, a new general C-C bond formation on the furoxan ring was developed. By taking advantage of the lability of furoxans, a wide variety of transformation of the synthesized furoxans have been demonstrated. Thus, this developed methodology enabled not only the modular synthesis of furoxans but also short-step transformations of carboxylic acids to a broad range of functional groups.
- Matsubara, Ryosuke,Kim, Hojin,Sakaguchi, Takaya,Xie, Weibin,Zhao, Xufeng,Nagoshi, Yuto,Wang, Chaoyu,Tateiwa, Masahiro,Ando, Akihiro,Hayashi, Masahiko,Yamanaka, Masahiro,Tsuneda, Takao
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supporting information
p. 1182 - 1187
(2020/02/15)
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- Rhodium-Catalyzed Rearrangement of S/Se-Ylides for the Synthesis of Substituted Vinylogous Carbonates
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An efficient rhodium-catalyzed unprecedented oxa-[2,3]-sigmatropic rearrangement of sulfur ylide derived from α-thioesters/ketones and diazo carbonyl compounds has been accomplished for the synthesis of various sulfur-tethered vinylogous carbonates in good to excellent yields. Important features of the developed reaction include wide functional group tolerance, excellent chemo- and regioselectivity, and efficient rearrangement involving the carbonyl motif. The present reaction also equally works well with α-selenoesters for the synthesis of seleno-containing vinylogous carbonates.
- Reddy, Angula Chandra Shekar,Anbarasan, Pazhamalai
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supporting information
p. 9965 - 9969
(2019/12/24)
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- Sulfonium ylide formation and subsequent C[sbnd]S bond cleavage of aromatic isopropyl sulfide catalyzed by hemin in aqueous solvent
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Heme is an abundant and widely existed cofactor for a variety of metalloenzymes, whose broader use is generally impeded by its high instability and poor solubility. Here we report an environment-benign and efficient strategy for the sulfonium ylide formation and subsequent C[sbnd]S bond cleavage of aromatic isopropyl sulfides, which was catalyzed by hemin in assistance of Triton X-100. This aqueous catalytic system exhibited good functional group tolerance to a variety of sulfides and diazo esters. And the reaction mechanism was preliminarily proposed on the basis of designed reactions. Furthermore, the cleavage of C[sbnd]S bond followed by introducing a functional ester group to aromatic sulfides, may potentially be employed for the late stage functionalization (LSF) of organosulfur drug in the future.
- Yan, Xiaojing,Li, Chang,Xu, Xiaofei,He, Quan,Zhao, Xiaoyong,Pan, Yuanjiang
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supporting information
p. 3081 - 3087
(2019/05/08)
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- Preparation method and application of novel ionic binuclear Schiff base titanium complex
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The invention provides a preparation method of a novel ionic binuclear Schiff base titanium complex and a synthetic method of applying the novel ionic binuclear Schiff base titanium complex to catalyze zinc powder and reduce disulfide or selenide to prepare sulfo(seleno) ester and dissymmetric sulfoether(selenide). The complex is a cationic binuclear Schiff base titanium complex, wherein titaniumatoms are bridged by oxygen atoms and are coordinated with a Schiff base ligand and a hydrone, and an ionic bond is formed by a cation part and an anion part of whole Schiff base titanium. The ionic binuclear Schiff base titanium complex is used as a catalyst, the zinc powder is used as a reducer, the disulfide(selenide) can be reduced and fractured, and the disulfide(selenide) can further and respectively react with anhydride, an alpha-bromo carbonyl compound and bromoalkane to prepare the sulfo(seleno) ester and the dissymmetric sulfoether(selenide). According to the preparation method provided by the invention, the defects that traditional lewis acid halide is deliquescent, an absolute solvent is used, conditions are strict and the like are overcome; an effective path for reducing the disulfide or selenide to prepare the sulfo(seleno) ester and the dissymmetric sulfoether(selenide) is provided, and the preparation method has the advantages of high yield, simpleness in operation andthe like.
- -
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Paragraph 0069; 0070
(2018/04/03)
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- Design, Synthesis, and Evaluation of New Sulfone Derivatives Containing a 1,3,4-Oxadiazole Moiety as Active Antibacterial Agents
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This study aimed to synthesize some new sulfone derivatives containing a 1,3,4-oxadiazole moiety and investigate their in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac), the pathogens
- Li, Pei,Hu, Deyu,Xie, Dandan,Chen, Jixiang,Jin, Linhong,Song, Baoan
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p. 3093 - 3100
(2018/04/05)
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- 2,5-substituent-1,3,4-oxadiazole sulfone derivative as well as preparation method and application thereof
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The invention discloses a 2,5-substituent-1,3,4-oxadiazole sulfone derivative as well as a preparation method and application thereof. The 2,5-substituent-1,3,4-oxadiazole sulfone derivative has a general formula shown in a formula (I), wherein R1 is 4-chlorine or 4-fluorine; and R2 is methyl, ethyl, propyl, n-butyl, n-pentyl, benzyl, 4-chlorobenzyl or 4-fluorobenzyl. The 2,5-substituent-1,3,4-oxadiazole sulfone derivative disclosed by the invention has good activity on rice bacterial leaf blight and xanthomonas citri and is simple in structure, simple in preparation technology and low in production cost. (The formula (I) is described in the specification).
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Paragraph 0093; 0094; 0105; 0106; 0117; 0118; 0129; 0130
(2018/06/16)
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- 2. 5 - Substituted - 1, 3, 4 - oxadiazoles double-sulfones derivatives, preparation method and application thereof (by machine translation)
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The invention discloses a 2, 5 - substituted - 1, 3, 4 - oxadiazoles double-sulfones derivatives, preparation method and application thereof, having formula (I) of the general formula, wherein: R1 For the 4 - chloro or 4 - fluoro; R2 For hydroxy, methyl, ethyl, benzyl, 4 - benzylic or 4 - fluorobenzyl. The invention relates to a rice BLB and citrus ulcer bacteria has better activity, the structure is simple, the preparation process is simple, the production cost is low. (by machine translation)
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Paragraph 0070; 0071; 0085; 0099; 0113; 0127
(2018/07/30)
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- Scope and Mechanism of Iridium Porphyrin-Catalyzed S-H Insertion Reactions between Thiols and Diazo Esters
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The insertion of carbenes derived from ethyl diazoacetate (EDA), methyl diazoacetate (MDA), methyl phenyldiazoacetate (MPDA), and methyl (p-tolyl)diazoacetate (MTDA) into the S-H bonds of aromatic and aliphatic thiols was catalyzed by (5,10,15,20-tetratolylporphyrinato)methyliridium(III), Ir(TTP)CH3, at ambient temperatures. Yields of the resulting thioether products were as high as 97% for aromatic thiols, with catalyst loadings as low as 0.07 mol %. Thiol binding to Ir(TTP)CH3 was measured at 23 °C by titration studies, providing equilibrium constants, Kb, ranging from 4.25 × 102 to 1.69 × 103 and increasing in the order p-nitrobenzenethiol a mechanism that involves a rate-limiting nucleophilic attack of thiols on an iridium-carbene species, where the major species present in the reaction solution is an inactive, hexacoordinate Ir-thiol complex.
- Dairo, Taiwo O.,Woo, L. Keith
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p. 927 - 934
(2017/04/21)
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- MYOGLOBIN-BASED CATALYSTS FOR CARBENE TRANSFER REACTIONS
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Methods are provided for carrying out carbene transfer transformations such as olefin cyclopropanation reactions, carbene heteroatom-H insertion reactions (heteroatom = N, S, Si), sigmatropic rearrangement reactions, and aldehyde olefination reactions with high efficiency and selectivity by using a novel class of myoglobin-based biocatalysts. These methods are useful for the synthesis of a variety of organic compounds which contain one or more new carbon-carbon or carbon-heteroatom (N, S, or Si) bond. The methods can be applied for conducting these transformations in vitro (i.e., using the biocatalyst in isolated form) and in vivo (i.e., using the biocatalyst in a whole cell system).
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-
Paragraph 00308; 00312
(2016/06/14)
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- Intermolecular carbene S-H insertion catalysed by engineered myoglobin-based catalysts
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The first example of a biocatalytic strategy for the synthesis of thioethers via an intermolecular carbene S-H insertion reaction is reported. Engineered variants of sperm whale myoglobin were found to efficiently catalyze this C-S bond forming transformation across a diverse set of aryl and alkyl mercaptan substrates and α-diazoester carbene donors, providing high conversions (60-99%) and high numbers of catalytic turnovers (1100-5400). Furthermore, the enantioselectivity of these biocatalysts could be tuned through mutation of amino acid residues within the distal pocket of the hemoprotein, leading to myoglobin variants capable of supporting asymmetric S-H insertions with up to 49% ee. Rearrangement experiments support a mechanism involving the formation of a sulfonium ylide generated upon attack of the thiol substrate to a heme-bound carbene intermediate. This journal is
- Tyagi, Vikas,Bonn, Rachel B.,Fasan, Rudi
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p. 2488 - 2494
(2015/03/30)
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- Fe-Mediated S-S Bond Cleavage and Its Application in the Synthesis of α-Arylthio Carbonyl Compounds
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In the presence of iron dust, diaryl disulfides react with α-bromo carbonyl compounds to obtain α-arylthio carbonyl compounds in good yield at 90 °C under an N2 atmosphere, using commercial dimethylformamide (DMF) as solvent. The possible reaction mechanism is that the disulfide is reduced by iron dust to give ArSFeSAr and then reacted with α-bromo carbonyl compounds to give product α-arylthio carbonyl compounds and FeBr2.
- He, Yun-Hua,Li, Ning-Bo,Chen, Jin-Yang,Qiu, Ren-Hua,Wang, Xie,Xu, Xin-Hua
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p. 1817 - 1822
(2015/08/06)
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- Copper-Catalyzed Synthesis of α-Thioaryl Carbonyl Compounds Through S-S and C-C Bond Cleavage
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A method to access α-thioaryl ketones and α-thioaryl esters employing copper acetate (hydrate) as catalyst and readily accessible diaryl disulfides and β-diketones (or β-keto esters) has been developed. Both alkyl- and aryl-substituted carbonyl compounds can be prepared. Copyright
- Zou, Liang-Hua,Priebbenow, Daniel L.,Wang, Long,Mottweiler, Jakob,Bolm, Carsten
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supporting information
p. 2558 - 2563
(2013/10/21)
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- Synthesis of some novel bioactive 4-oxy/thio substituted-1H-pyrazol-5(4H)-ones via efficient cross-Claisen condensation
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α-Oxy/thio substituted-β-keto esters were synthesized through an efficient cross-Claisen condensation of aryl oxy/thio acetic acid ethyl esters with acid chlorides, then it is converted in situ into 4-oxy/thio substituted-1H-pyrazol-5(4H)-ones by the addition of hydrazine or hydrazine derivatives and screened for their antibacterial, antifungal activities.
- Venkat Ragavan,Vijayakumar,Suchetha Kumari
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experimental part
p. 3852 - 3857
(2009/12/04)
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- Identification of anthranilic acid derivatives as a novel class of allosteric inhibitors of hepatitis C NS5B polymerase
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A series of potent anthranilic acid-based inhibitors of the hepatitis C NS5B polymerase has been identified. The inhibitors bind to a site on NS5B between the thumb and palm regions adjacent to the active site as determined by X-ray crystallography of the enzyme-inhibitor complex. Guided by both molecular modeling and traditional SAR, the enzyme activity of the initial hit was improved by approximately 100-fold, yielding a series of potent and selective NS5B inhibitors with IC50 values as low as 10 nM. These compounds were also inhibitors of the HCV replicon in cultured HUH7 cells.
- Nittoli, Thomas,Curran, Kevin,Insaf, Shabana,DiGrandi, Martin,Orlowski, Mark,Chopra, Rajiv,Agarwal, Atul,Howe, Anita Y. M.,Prashad, Amar,Floyd, M. Brawner,Johnson, Bernard,Sutherland, Alan,Wheless, Karen,Feld, Boris,O'Connell, John,Mansour, Tarek S.,Bloom, Jonathan
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p. 2108 - 2116
(2008/02/06)
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- Insertion of ethyl diazoacetate into N-H and S-H bonds catalyzed by ruthenium porphyrin complexes
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Ruthenium porphyrin complexes catalyze insertion of ethyl diazoacetate into sulfur-hydrogen and nitrogen-hydrogen bonds under mild conditions and with reasonable to very good yields.
- Galardon, Erwan,Le Maux, Paul,Simonneaux, Gerard
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p. 2455 - 2456
(2007/10/03)
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- Organic reactions catalyzed by methylrhenium trioxide: Reactions of ethyl diazoacetate and organic azides
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Methylrhenium trioxide (CH3ReO3 or MTO) catalyzes several classes of reactions of ethyl diazoacetate, EDA. It is the first high valent oxo complex for carbene transfer. Under mild conditions and in the absence of other substrates, EDA was converted to a 9:1 mixture of diethyl maleate and diethyl fumarate. In the presence of alcohols, α-alkoxy ethyl acetates were obtained in good yield. The yields dropped for the larger and more branched alcohols, the balance of material being diethyl maleate and fumarate. An electron-donating group in the para position of phenols favors the formation of α-phenoxy ethyl acetates. The use of EDA to form α-thio ethyl acetates and N-substituted glycine ethyl esters, on the other hand, is hardly affected by the size or structure of the parent thiol or amine, with all of these reactions proceeding in high yield. MTO-catalyzed cycloaddition reactions occur between EDA and aromatic imines, olefins, and carbonyl compounds. Three-membered ring products are formed: aziridines, cyclopropanes, and epoxides, respectively. The reactions favor the formation of trans products, and provide a convenient route for the preparation of aziridines. Intermediate carbenoid and nitrenoid species have been proposed. In the presence of an oxygen source such as an epoxide, ethyl diazoacetate and azibenzil are converted to an oxalic acid monoethyl ester and tobenzil; at the same time the epoxide was converted to an olefin. These results provide further support for the proposed intermediate, a cyclic species containing Re, O, and CHCO2Et (or, occasionally, CPhC(O)Ph)in a three-membered ring.
- Zhu, Zuolin,Espenson, James H.
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p. 9901 - 9907
(2007/10/03)
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- Kinetics and Mechanism of Oxidation of Ethyl Phenylthioacetates by Bromamine-B
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The kinetics of oxidation of several substituted ethyl phenylthiacetates by bromamine-B (sodium salt of N-bromobenzenesulfonamide) has been studied in 50percent (v/v) aqueous ethanol medium.Disodium hydrogenphosphate and sodium dihydrogenphosphate buffer
- Gurumurthy, Rajagopal,Sathiyanarayanan, Kulathu Iyer,Gopalakrishnan, Mannathusamy
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p. 1096 - 1100
(2007/10/02)
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- SYNTHESIS AND SPECTRAL STUDIES OF SOME NOVEL ETHYL (SUBSTITUTED PHENYLTHIO) ACETATE AND PROPIONATE DERIVATIVES
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Ethyl (substituted phenylthio) acetate and propionate derivatives have been synthesised, their structures were proved by IR, NMR and mass spectra.Key words: Arylthioacetates; arylthiopropionates; NMR- and mass spectra
- Hamed, Ezzat E.,El-Bardan, A. A.,Moussa, Adel M.
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p. 269 - 274
(2007/10/02)
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- Conversion of 2-Sulfinylated 2-Alkenoate Esters to (2E,4E)-2,4-Alkadienoate Esters by Pyrolysis
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Thermal reaction of ethyl (2E)-2-phenylsulfinyl-2-alkenoates (E-2) prepared from aldehydes and ethyl 2-phenylsulfinylacetate have been investigated.Refluxing of E-2 or their Z-isomers in xylene resulted in the formation of ethyl (2E,4E)-2,4-alkanedioates accompanied by ethyl (2E)-4-hydroxy-2-alkenoates.Ethyl 2-cycloalkylidene-2-phenylsulfinylacetates were found to be more susceptible to pyrolysis.The enoate esters (2) undergo migration of their carbon-carbon double bond and then sigmatropic rearrangement to benzenesulfenate esters, followed by thermolytic extrusion of a benzenesulfenic acid probably via ethyl(2E)-4-phenylsulfinyl-2-alkenoates to afford ethyl (2E,4E)-2,4-alkadienoates.
- Tanikaga, Rikuhei,Nozaki, Yoshihito,Nishida, Masaharu,Kaji, Aritsune
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p. 729 - 733
(2007/10/02)
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- Reactions of Thionitrites or Thionitrates with Carbanions
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Reaction of several thionitrites (RSNO) or thionitrates (RSNO2) with carbanions such as Grignard reagents, alkyllithium, or the carbanion of diethyl malonate gave C-alkythio derivatives such as sulfides or diethyl (alkythio)malonates.
- Shinhama, Koichi,Kim, Yong Hae,Oae, Shigeru
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p. 1771 - 1772
(2007/10/02)
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