- Tuning the surface composition of novel metal vanadates and its effect on the catalytic performance
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Tuning the surface composition of metal vanadates using different cations leads to the development of a new class of highly effective catalysts tested in the ammoxidation of 2-methylpyrazine. Especially, an enrichment of V in the near-surface region is beneficial for improved selectivity. With this approach, a knowledge based optimisation of the catalysts was possible for the first time, which indeed led to highly efficient novel LaVOx catalysts with a high yield of 2-cyanopyrazine (≥85%) and extremely high space-time-yields (ca. 525 g-1CP kg-1cat h-1).
- Dhachapally, Naresh,Kalevaru, V. Narayana,Radnik, Joerg,Martin, Andreas
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- Influence of polyoxometalate structure in ammoxidation of 2-methylpyrazine
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Keggin, Wells-Dawson and Preyssler structured polyoxometalates (POMs) were synthesized by different methodologies. The POMs were used as catalysts for ammoxidation of 2-methylpyrazine. The structural properties of POMs were determined by XRD, SEM, DRIFT, DRUV-vis, H2-TPR, NH3-TPD and N2-physisorption. Preyssler POM sample showed highest 2-methylpyrazine conversion (69%) and 2-cyanopyrazine selectivity (98%) at 380 °C. Superior performance of Preyssler POM could be attributed to its redox behavior and relatively strong acid sites. Large number of ammonium ions in the secondary structure of Preyssler POM could also enhance the transformation of oxygenated 2-methylpyrazine species into 2-cyanopyrazine. A correlation between the amount of ammonium content of POMs and their catalytic ammoxidation activity was obtained.
- Al-Shehri, Abdulmohsen,Katabathini, Narasimharao
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- Ammoxidation of 2-Methylpyrazine. Characterisation of Catalyst
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The effect of changing the relative ratios of the active components in Sb-V-Mn mixed oxides, their concentration on the support and the nature of the latter has been analysed by employing several techniques, such as X-ray diffraction, scanning electron microscopy, electron probe microanalysis and electron spin resonance spectroscopy, together with chemical analysis, a titration of the surface acidity, and determinations of both the B.E.T. surface area and the porosity.A close dependence of activity and selectivity on the nature of the support was observed, connected with the ability of the latter to supress the formation of microporosity.The catalytic activity is due to Sb4+ species.V and Mn both act as a structural promoter, conferring electrical conductivity on the solid and so improving the rapid electron transfer from the bulk to the surface, and vice versa.
- Forni, Lucio,Oliva, Cesare,Rebuscini, Claudio
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- Ammoxidation of 2-methylpyrazine to 2-cyanopyrazine over Nb-V oxides: Marked effect of the Nb/V ratio on the catalytic performance
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A series of bulk Nb-V-containing mixed oxide catalysts with varying Nb/V ratios were synthesized and studied by various solid-state characterization methods. Their catalytic performance was evaluated for the gas phase ammoxidation of 2-methylpyrazine (MP) to 2-cyanopyrazine (CP) that has received growing interest in the chemical industry, recently. The catalysts were characterised by BET-SA, XRD, UV-vis DRS, FTIR, XPS, and TEM. The BET surface area decreased continuously with increase in vanadia content. XRD data confirmed the changes in the crystalline phases with altering Nb/V ratios. UV-vis DRS and FTIR spectroscopic results showed the formation of various kinds of V-oxide species in the catalysts with change in V content. An increase in the concentration of vanadium changes the nature of VOx species from isolated vanadia species to polymeric vanadia species and then to crystalline vanadia species. Among all the catalysts, the Nb-V-O catalyst with a Nb/V ratio of 1 exhibited the best performance in the ammoxidation reaction (i.e. X-MP ~100% and selectivity to 2-CP ~70%). Additionally, a very high space-time yield of CP (>440 gCP kgcat-1 h-1) could be successfully achieved. This best catalyst sample revealed two-dimensional polymeric V-oxide species. TEM and SEM showed the formation of a rod-shaped nanoparticle morphology. XPS data revealed that the vanadium is present in two oxidation states (V5+ and V4+) in the fresh catalyst (Nb/V = 1) and only one oxidation state (V5+) in the spent catalyst. the Partner Organisations 2014.
- Dhachapally, Naresh,Kalevaru, V. Narayana,Martin, Andreas
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- Metal vanadate catalysts for the ammoxidation of 2-methylpyrazine to 2-cyanopyrazine
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The ammoxidation of 2-methylpyrazine to 2-cyanopyrazine was carried out in a fixed bed metal reactor in the temperature range of 320-460 °C using a series of metal vanadate-containing solids (MV) as catalysts. These solids named as AlVO4, FeVO4, CrVO4, NbVO5, LaVO4 and BiVO4 were prepared with a nominal V/M ratio = 1 always using the same synthesis procedure. Fresh and spent solids were characterized by X-ray diffraction, UV-vis DRS, XPS and pyridine-FTIR & ESR spectroscopy. The results revealed that the phase composition, near-surface-region behaviour and catalytic properties strongly depend on the nature of the metal used in MV solids. XRD showed the formation of crystalline MV phases in case of LaVO4 and BiVO4; whereas FeVO 4 and CrVO4 exhibited poor crystallinity only. AlVO 4 sample revealed the clear formation of crystalline V 2O5 whereas in NbVO5 only a small proportion of V2O5 was detected. XPS depicted that the enrichment of vanadium in the near-surface-region is clearly dependent on the type of MV. It can be concluded that high near-surface-region V/M molar ratios promote the selectivity to cyanopyrazine but reduce the catalytic activity and vice versa. NbVO5 showed the best catalytic performance compared to all other MVs. Almost 69% yield of 2-cyanopyrazine at total conversion could be successfully obtained.
- Dhachapally, Naresh,Kalevaru, Venkata N.,Brückner, Angelika,Martin, Andreas
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- Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions
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Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is
- Kim, Se Hyun,An, Ju Hyeon,Lee, Jun Hee
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supporting information
p. 3735 - 3742
(2021/05/04)
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- Synthesis of nitriles via the iodine-mediated dehydrosulfurization of thioamides
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A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I2) is described herein. The reaction of thioamides with I2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion from thioureas to cyanamides.
- Murata, Yuki,Iwasa, Hitomi,Matsumura, Mio,Yasuike, Shuji
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p. 679 - 681
(2020/07/30)
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- Preparation process of pyrazinamide
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A preparation process of pyrazinamide comprises the following steps: (1) synthesis of 2-methylpyrazine: putting a catalyst I into a reactor I, and performing reducing for 4 hours; adding 2-methylpyrazine into the reactor I, then adding ethylenediamine and 1, 2-propylene glycol, carrying out gas-solid phase contact catalytic reaction in the reactor I, cooling a mixture generated by the reaction through a condenser, feeding the mixture into a receiver, taking tail gas, and performing absorbing, emptying and separating to obtain 2-methylpyrazine, (2) chemical base catalysis; putting the catalystII into a reactor II, introducing an aqueous solution of 2-methylpyrazine in a mass ratio of (1:10)-(1:20) into the reactor II through a metering pump, introducing ammonia gas and air, controlling thetemperature of the reaction system to be 3-6 DEG C, maintaining the pH value to be 9-10, performing reacting for 1-2 hours, and performing heating to 20-30 DEG C to obtain 2-cyanopyrazine; and (3) synthesis of pyrazinamide. The preparation process of pyrazinamide has the advantages of the simple process, the high conversion rate, no generation of by-product pyrazinic acid, the good economic benefits and the wide application prospect.
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Paragraph 0023; 0025; 0028-0029; 0032; 0034; 0037; 0039;
(2020/07/24)
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- METHOD FOR PRODUCING AROMATIC NITRILE COMPOUND AND METHOD FOR PRODUCING CARBONATE ESTER
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Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of dehydration reaction and significantly improves the reaction speed at a pressure close to normal pressure. Furthermore, the above-described production method is applied to a carbonate ester production method to provide a method for producing carbonate ester efficiently. The above-described objects are achieved by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses diphenylether.
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Paragraph 0099; 0101; 0102
(2019/07/03)
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- Corresponding amine nitrile and method of manufacturing thereof
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The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.
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- General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP
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A new and general nickel-catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2·6H2O/dppf/Zn as the catalytic system and DMAP as the additive, allowing the cyanation to occur under mild reaction conditions (50-80 °C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.
- Zhang, Xingjie,Xia, Aiyou,Chen, Haoyi,Liu, Yuanhong
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supporting information
p. 2118 - 2121
(2017/04/27)
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- Ammoxidation of 2-methyl pyrazine on supported ammonium salt of 12-molybdophosphoric acid catalysts: The influence of nature of support
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Influence of the nature of support on the formation of catalytically active species was investigated to clarify the key factor for the synthesis of supported ammonium salt of 12-molybdophosphoric acid (AMPA) catalyst which maintains the activity of ammoxidation during 2-methylpyrazine reaction. With this aim, different loadings of niobia-, silica- and alumina-, supported AMPA catalysts were prepared. The AMPA loading was varied in the range of 5-25 wt%. The synthesized solids were characterized by nitrogen adsorption for BET surface area, XRD and 31P MAS NMR techniques. All the AMPA-supported samples are poorly crystalline even after 25 wt% AMPA loading. Investigations using 31P MAS NMR spectroscopy of samples revealed that Keggin ion existed as at least five different species on the supports. The investigated properties were acidity of the support and amount of AMPA loading on the support. Active sites for the ammoxidation of MP on supported AMPA catalysts seem to be the interacted and/or the lacunary species. Maximum catalytic activity could be obtained at lower loadings with AMPA deposited on acidic supports whereas the less acidic supports require higher loading. It was found that in order to efficiently generate the active interactive species, the support must have an acidity which promotes the formation of support-AMPA interactive species. It is possible to enhance the catalytic activity of the supported AMPA catalyst for ammoxidation of 2-methylpyrazine by controlling the acidity of the support and AMPA loading on the support.
- Narasimharao, Katabathini,Babu, B. Hari,Lingaiah,Prasad, P. S. Sai,Al-Thabaiti, Shaeel A.
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p. 487 - 498
(2014/06/09)
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- Palladium acetate catalyzed cyanation of aryl halides using Buchwald's 2-(di-t-butylphosphino)-1,1'-binaphthyl
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An application of Buchwald's 2-(di-t-butylphosphino)-1,1'-binaphthyl 1 in palladium acetate catalyzed cyanation of aryl halides was developed. Using this ligand, aryl chlorides substituted with both electron donating or withdrawing groups afforded the desired cyano products in excellent yields. The corresponding aryl bromides gave higher yields within shorter time. Heteroaryl chlorides also reacted under the similar conditions to give the cyano products in excellent yields.
- Wang, Bei,Zhao, Rulin,Chen, Bang-Chi,Balasubramanian, Balu
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experimental part
p. 47 - 52
(2010/09/09)
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- PROCESS FOR THE PREPARATION OF CYANO-SUBSTITUTED-NITROGEN-CONTAINING HETEROARYL COMPOUNDS
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The present invention provides compounds and methods that can be used to convert nitrogen-containing-heteroaryl carboxamides to the corresponding nitrogen-containing-heteroaryl nitriles reliably in one step, with high yields and without the need for elaborate purification.
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Page/Page column 12-13
(2009/12/05)
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- Mild and general methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides
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New methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides have been developed, featuring sterically demanding, electron-rich phosphines. Highly challenging electron-rich aryl chlorides, in addition to electron-neutral and electron-deficient substrates, as well as nitrogen- and sulfur-containing heteroaryl chlorides can all undergo efficient cyanation under relatively mild conditions using readily available materials. In terms of substrate scope and temperature, these methods compare very favorably with the state-of-the-art cyanations of aryl chlorides.
- Littke, Adam,Soumeillant, Maxime,Kaltenbach III, Robert F.,Cherney, Robert J.,Tarby, Christine M.,Kiau, Susanne
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p. 1711 - 1714
(2008/02/02)
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- A convenient new procedure for converting primary amides into nitriles
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An operationally simple and high-yielding procedure has been developed for the conversion of primary amides to the corresponding nitriles, using ethyl dichlorophosphate/DBU as the mild dehydrating agent. The Royal Society of Chemistry.
- Kuo, Chun-Wei,Zhu, Jia-Liang,Wu, Jen-Dar,Chu, Cheng-Ming,Yao, Ching-Fa,Shia, Kak-Shan
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p. 301 - 303
(2007/10/03)
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- Cyanidation of halogen compounds and esters catalyzed by PEG400 without solvent
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Primary aliphatic and aromatic nitriles were synthesized in excellent yields (84-96%) and purity by the cyanidation of halogen compounds and esters with dry powdered sodium cyanide catalysed by phase transfer catalyst PEG400 under solvent-free conditions.
- Cao,Chen,Pei
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p. 2203 - 2207
(2007/10/03)
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- Interaction-induced enhancement in the activity and selectivity of a titania-supported ammonium salt of a 12-molybdophosphoric acid catalyst during ammoxidation of 2-methylpyrazine
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A titania-supported ammonium salt of 12-molybdophosphoric acid has been synthesized, and the salt - support interaction, which enhanced the reaction rate, has been correlated with the activity of the catalyst in the ammoxidation of 2-methylpyrazine.
- Rao,Gopinath,Kumar,Suryanarayana,Sai Prasad
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p. 2088 - 2089
(2007/10/03)
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- A new method for the generation of nitriles from aldoximes
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A mild and efficient method for the stereoselective dehydration of α-aldoximes to the corresponding nitriles is described which utilises methyl (carboxysulfamoyl)triethylammonium hydroxide inner salt (Burgess reagent) as the dehydrating agent.
- Jose, Binoy,Sulatha,Madhavan Pillai,Prathapan, Sreedharan
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p. 1509 - 1514
(2007/10/03)
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- 5-alkyl-l-pyrazinecarboxamides, 5-alkyl-2-pyrazinecarbonitriles and 5-alkyl-2-acetylpyrazines as synthetic intermediates for antiinflammatory agents
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2-Pyrazinecarbonitrile, 2-acetylpyrazine, 5-alkyl-2-pyrazinecarboxamides, 5-alkyl-2-pyrazinecarbonitriles and 5-alkyl-2-acetylpyrazines were prepared as intermediates for use in synthesis of potential antiinflammatory agents. The results of the homolytic alkylation of pyrazinecarboxamide were compared with published data. 2-Acetylpyrazine and its 5-(1,1-dimethylethyl) derivative were screened for biological activity, but no interesting effect was found.
- Opletalova, Veronika,Patel, Asmita,Boulton, Michael,Dundrova, Alice,Lacinova, Eva,Prevorova, Marta,Appeltauerov, Martina,Coufalova, Milada
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p. 1093 - 1101
(2007/10/03)
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- Studies on Pyrazines. Part 22. Lewis Acid-Mediated Cyanation of Pyrazine N-Oxides with Trimethylsilyl Cyanide: New Route to 2-Substituted 3-Cyanopyrazines
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Reaction of 3-substituted pyrazine 1-oxides with trimethylsilyl cyanide in the presence of triethylamine in acetonitrile gave the corresponding cyanopyrazines, yields of which depended remarkably on the substituent.Electron-donating groups enhanced the cyanation with high regioselectivity to 2-substituted 3-cyanopyrazines, while a chloro substituent suppressed the conversion.Addition of zinc halide to the reaction mixture, in most cases, increased the reactivity and improved the regioselectivity.On the other hand, the N-oxides carrying an electron-withdrawing methoxycarbonyl or N-butylcarbamoyl group underwent the cyanation, without need for the Lewis acid, to provide a mixture of nearly equal amounts of 2-substituted 3- and 5-cyanopyrazines.The latter compound was exclusively obtained when 3-methoxycarbonyl- or 3-cyanopyrazine 1-oxide was treated with diethoxyphosphoryl cyanide.
- Sato, Nobuhiro,Shimomura, Yuji,Ohwaki, Yoshie,Takeuchi, Ryo
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p. 2877 - 2882
(2007/10/02)
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- 4-benzylpiperazines useful as neuroleptics
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Compounds of formula (I) in which the broken line forms a phenyl, naphthyl, pyridyl, indolizine, pyrrolo[1,2-a]pyrazine, pyrrolo[1,2-a]pyrimidine or pyrrolo[1,2-c]pyrimidine ring-system, R=H, halogen, OH, alkyl, alkyloxy or alkylthio, R'=H, halogen, alkyl, alkyloxy, alkylthio, CN or CF3, n and p=1, 2 or 3, the alkyl radicals having 1 to 4 C in a straight or branched chain. These products are useful as neuroleptics. STR1
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- Process for preparing nitriles
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A heteroaromatic nitrile is prepared in a high selectivity and yield by catalytically reacting an alkyl-substituted heteroaromatic compound with molecular oxygen and ammonia in a molar ratio of oxygen to ammonia of not larger than 1.6:1 in a gaseous phase in the presence of a catalyst comprising a vanadium-phosphorus oxide of the formula: wherein x, y and z represent atomic ratios of phosphorus, antimony and oxygen to vanadium, respectively, and x is from 0.1 to 5, y is 0 to 8 and z is defined from the valencies of other elements.
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- NEW BINUCLEAR HETEROCYCLIC LIGANDS SHARING AN α-DIIMINE MOIETY AND THEIR RUTHENIUM(II) TRIS-CHELATES
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A number of chelating heterocyclic ligands which include pyridine, pyrazine, 1,3-heteroazole, and/or 1,2,4-heterodiazole moieties, have been prepared and characterized in order to tune the excited state properties of the corresponding Ru(II) complexes.The detailed study on the binuclear heterocycles by using uv, 1H- and 13C-nmr spectroscopy, as well as mass spectrometry, is also provided.The synthesis and spectral data (uv, ir, 1H- and 13C-nmr) of the ruthenium(II) tris-chelates is also included.
- Orellana, Guillermo,Alvarez-Ibarra, Carlos,Quiroga, Maria Luz
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p. 731 - 742
(2007/10/02)
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- Catalysts for the production of 2-cyanopyrazine
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For the catalytic reaction of 2-methylpyrazine with ammonia and oxygen to form 2-cyanopyrazine there are used compounds of the elements antimony, vanadium, and oxygen and at least one of the elements iron, copper, titanium, cobalt, manganese, and nickel, whereby the atomic ratio of antimony to vanadium is greater than 1 and which contain besides these compounds a lattice layer silicate and a highly dispersed silica. These catalysts are very selective and result in high yields and high space-time-yields.
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- N-[(5-Halo-2,6-(substituted)pyrazinyl)methylene]amine antimicrobial compounds, compositions and use
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Antimicrobial compounds of the formula: STR1 wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R1 is hydrogen; or loweralkyl; R2 is (CH2)n COORa, where Ra is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R1 and R2 are taken together with an oxygen or nitrogen atom or form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; R3 is hydrogen; straight or branched C1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C1-3 alkyl, C1-3 alkoxy, halo, and mono- or di-C1-3 alkyl substituted amino; heteroaryl; formylC2-4 alkenyl; or C2-4 alkenyl; and R4 is straight or branched C1-8 alkyl; loweralkoxy; hydroxy; loweralkoxycarbonylmethyl; benzyl; or benzyl substituted with up to two members selected from the group consisting of halo, loweralkyl, and loweralkoxy; are useful in various agricultural and industrial applications.
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- 3-Acyl-2-(substituted) amino-5-halo-6-(substituted) pyrazine antimicrobial compounds, compositions and use
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Antimicrobial compounds of the formula: STR1 wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R1 is hydrogen; or loweralkyl; R2 is hydroxyloweralkyl; (CH2)n COORa, where Ra is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R1 and R2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; and R3 is hydrogen; straight or branched C1-8 alkyl, provided that when R3 is hydrogen or C1-8 alkyl, R is other than halo; aryl; aryl substituted with up to two members selected from the group consisting of C1-3 alkyl, C1-3 alkoxy, halo, and mono- or di-C1-3 alkyl substituted amino; heteroaryl; formyl C2-4 alkenyl; or C2-4 alkenyl; are useful in various agricultural and industrial applications.
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- 2-(Substituted)amino-3-cyano-5-halo-6-(substituted)-pyrazine antimicrobial compounds, compositions and use
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Antimicrobial compounds of the formula: STR1 wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R1 is hydrogen; or loweralkyl; R2 is (CH2)n COOR3, where R3 is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; and R1 and R2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; are useful in various agricultural and industrial areas.
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