- Investigation of BiVO4 structure variations on the dichlorotoluene ammoxidation performance
-
In this study, BiVO4 synthesized by hydrothermal and calcination methods were explored as catalysts in the ammoxidation of dichlorotoluenes to shed light on the structure-reactivity correlations. The BiVO4 samples were characterized by X-ray diffraction (XRD), temperature-programmed reduction (TPR), Brunauer–Emmett–Teller (BET), and UV–Vis spectrophotometry. The results showed that the catalytic activity of BiVO4 greatly relied on the structure variations. The hydrothermal prepared BiVO4 exhibited better catalytic activities as a consequence of its greater structure deformation, with maximum yields of 73.1, 72.2, and 70.8% for 3,4-, 2,4- and 2,6- dichlorobenzonitrles, respectively.
- Li, Xiongjian,Huang, Chi
-
p. 866 - 870
(2020/12/30)
-
- SO 2 F 2 -Promoted Dehydration of Aldoximes: A Rapid and Simple Access to Nitriles
-
A rapid, simple and mild process for the dehydration of aldoximes to give the corresponding nitriles, which utilizes SO 2 F 2 as an efficient reagent, has been developed. A variety of (hetero)arene, alkene, alkyne and aliphatic aldoximes proceeded with high efficiency to afford nitriles in excellent to quantitative yields with great functional group compatibilities in acetonitrile under ambient conditions. Furthermore, an eco-friendly synthetic protocol to access nitriles from aldehydes with ortho -, meta - and para -nitrile groups was also described in aqueous methanol by using inorganic base Na 2 CO 3, and a one-pot synthetic strategy to generate nitriles from aldehydes was proved to be feasible.
- Ding, Chengrong,Mei, Guangyao,Wang, Haibo,Zhang, Guofu,Zhao, Yiyong
-
supporting information
p. 1484 - 1488
(2019/07/15)
-
- Arene Cyanation via Cation-Radical Accelerated-Nucleophilic Aromatic Substitution
-
Herein we describe a cation radical-accelerated-nucleophilic aromatic substitution (CRA-SNAr) of alkoxy arenes utilizing a highly oxidizing acridinium photoredox catalyst and acetone cyanohydrin, an inexpensive and commercially available cyanide source. This cyanation is selective for carbon-oxygen (C-O) bond functionalization and is applicable to a range of methoxyarenes and dimethoxyarenes. Furthermore, computational studies provide a model for predicting regioselectivity and chemoselectivity in competitive C-H and C-O cyanation of methoxyarene cation radicals.
- Holmberg-Douglas, Natalie,Nicewicz, David A.
-
supporting information
p. 7114 - 7118
(2019/09/07)
-
- Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides to Form Nitriles
-
A palladium(II) catalyst, in the presence of Selectfluor, enables the efficient and chemoselective transformation of primary amides into nitriles. The amides can be attached to aromatic rings, heteroaromatic rings, or aliphatic side chains, and the reactions tolerate steric bulk and electronic modification. Dehydration of a peptaibol containing three glutamine groups afforded structure-activity relationships for each glutamine residue. Thus, this dehydration can act similarly to an alanine scan for glutamines via synthetic mutation.
- Al-Huniti, Mohammed H.,Rivera-Chávez, José,Colón, Katsuya L.,Stanley, Jarrod L.,Burdette, Joanna E.,Pearce, Cedric J.,Oberlies, Nicholas H.,Croatt, Mitchell P.
-
supporting information
p. 6046 - 6050
(2018/09/27)
-
- Aerobic Oxidative Dehydrogenation of Amines Catalyzed by a Recoverable Ruthenium Catalyst under Mild Reaction Conditions
-
A highly active catalyst based on perruthenate ions supported inside the channels of periodic mesoporous organosilica with a bridged imidazolium ionic liquid framework (Ru@PMO-IL) was developed. The material was found to be an efficient, durable, and recoverable catalyst for the oxidative dehydrogenation of various types of amines such as benzylic, aliphatic, and cyclic aliphatic amines under mild reaction conditions. The products were obtained in excellent yields with excellent selectivities.
- Karimi, Babak,Yari, Omolbanin,Khorasani, Mojtaba,Vali, Hojatollah,Mansouri, Fariborz
-
p. 1783 - 1787
(2018/01/27)
-
- NH3?H2O: The Simplest Nitrogen-Containing Ligand for Selective Aerobic Alcohol Oxidation to Aldehydes or Nitriles in Neat Water
-
Aqueous ammonia (NH3?H2O) has been shown to serve as the simplest nitrogen-containing ligand to effectively promote copper-catalyzed selective alcohol oxidation under air in water. A series of alcohols with varying electronic and steric properties were selectively oxidized to aldehydes with up to 95 % yield. Notably, by increasing the amount of aqueous ammonia in neat water, the exclusive formation of aryl nitriles was also accomplished with good-to-excellent yields. Additionally, the catalytic system exhibits a high level of functional group tolerance with ?OH, ?NO2, esters, and heteroaryl groups all being amenable to the reaction conditions. This one-pot and green oxidation protocol provides an important synthetic route for the selective preparation of either aldehydes or nitriles from commercially available alcohols.
- Zhang, Guofu,Ma, Danting,Zhao, Yiyong,Zhang, Guihua,Mei, Guangyao,Lyu, Jinghui,Ding, Chengrong,Shan, Shang
-
p. 885 - 889
(2018/12/10)
-
- Metal-free HNO3/TEMPO-catalyzed conversion of benzyl alcohols to aromatic nitriles with oxygen molecule as the terminal oxidant
-
A non-metal catalytic method for the aerobic conversion of primary alcohols to aromatic nitriles via a single-step operation was developed. A series of primary benzyl alcohols underwent this transformation to give the targeted products in moderate to high yields under the catalysis of TEMPO/ HNO3.
- Zhao, Bo,Ren, Yun-Lai,Ren, Fangping,Tian, Xinzhe,Zhao, Shuang
-
supporting information
p. 627 - 632
(2019/05/01)
-
- Hydrothermal Synthesis of Urchin-like W-V-O Nanostructures with Excellent Catalytic Performance
-
Urchinlike W-V-O microspheres have been successfully synthesized for the first time by a one-pot hydrothermal approach. The as-synthesized W-V-O material was characterized by several techniques such as XRD, SEM, TEM, FTIR, EDS, BET, and Raman spectroscopy. The characterization results have revealed that the W-V-O microspheres consist of numerous one-dimensional nanobelts radially grown from the center. The typical nanobelts display rectangular cross sections with lengths of several micrometers, widths of about 50 nm, and thicknesses of approximately 10-20 nm. Vanadium oxides are dispersed highly either on the external surface or inside the channel surface of the hexagonal WO3 structure. In addition, the as-obtained urchin-like W-V-O material was explored as a catalyst for the ammoxidation of 2,4- and 2,6-dichlorotoluene to the corresponding nitriles. The catalytic results have indicated that the W-V-O nanostructures show excellent performance with yields of 2,4- and 2,6-dichlorobenzonitrile respectively reaching up to 77.3 and 75.1%, which are the highest among the previously reported catalysts with two components. The formation process of the urchinlike W-V-O microspheres was simply investigated.
- Li, Xiongjian,Sun, Li,Hu, Mingjie,Huang, Ronghua,Huang, Chi
-
p. 14758 - 14763
(2018/11/23)
-
- Polyethylene glycol supported phosphorus chloride: An efficient and recyclable catalyst for the preparation of nitriles from aldoximes
-
Polyethylene glycol (PEG) supported phosphorus chloride has been developed and used as an efficient and recyclable catalyst for dehydration of various aldoximes into the corresponding nitriles. This protocol has many advantages such as high conversion, high selectivity, short reaction time, mild reaction conditions, and simple experimental procedure.
- Zhang, Xiao-Lan,Sheng, Shou-Ri,Wei, Mei-Hong,Liu, Xiao-Ling
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p. 513 - 517
(2017/05/01)
-
- A 4, 6 - double-halogenated isophthalonitrile preparation method (by machine translation)
-
The present invention relates to the technical field of the synthesis of pharmaceutical intermediates, in particular to a 4, 6 - double-halogenated isophthalonitrile preparation method, through the use of cheap and easily obtained 2, 4 - double-halo benzoic acid as the raw material, the reaction of the halide, the amidation reaction, dehydration reaction, the nitration reaction, reduction reaction, the diazotization reaction, the substitution reaction for the synthesis of 4, 6 - double-halogenated isophthalonitrile; the total yield can be 21.5%. The process route is easily obtained and cheap materials, few by-products, the purification treatment is the process is simple, easy to realize industrial production. (by machine translation)
- -
-
Paragraph 0024; 0025; 0040; 0041; 0056; 0057; 0072; 0073
(2017/07/21)
-
- Design and Synthesis of Novel 4-Phenoxyquinolines Bearing 3-Hydrosulfonylacrylamido or 1H-Imidazole-4-carboxamido Scaffolds as c-Met Kinase Inhibitors
-
A series of novel 6,7-disubstituted-4-phenoxyquinoline derivatives bearing (E)-3-hydrosulfonylacrylamido or 1H-imidazole-4-carboxamido moieties were designed, synthesized and evaluated for their cytotoxicity against A549, MKN-45, and HT-29 cancer cell lines in vitro. All the target compounds showed moderate to significant cytotoxic activity against the tested cells with IC50 values ranging from 0.13 to 2.65 μM. Five of them were further examined for their inhibitory activity against c-Met kinase, which identified compound 30 as a promising agent (c-Met IC50 = 1.52 nM) with IC50 values of 0.24, 0.45, and 0.13 μM against HT-29, MKN-45, and A549 cells, respectively.
- Wang, Jiao,Xie, Lijun,Wang, Yu,Wang, Xiaoqiang,Xi, Shuancheng,Zeng, Tianfang,Gong, Ping,Zhai, Xin
-
-
- Design, synthesis and biological evaluation of novel 4-(2-fluorophenoxy)quinoline derivatives as selective c-Met inhibitors
-
Two novel series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives bearing 1H-imidazole-4-carboxamido or (E)-3-hydrosulfonylacrylamido motifs (16–31 and 32–42) were designed, synthesized and evaluated for their in vitro cytotoxic activity. Most of the compounds exhibited moderate to excellent potency against tested three cell lines, and fifteen compounds were further examined for their inhibitory activity against c-Met kinase. The most promising compound 16 (c-Met kinase [IC50]?=?1.1?nM) demonstrated high selectivity and remarkable cytotoxicity against HT-29, MKN-45 and A549 cells with IC50values of 0.08, 0.22 and 0.07?μM, which were 3.1-, 1.4- and 2.1-fold more active than Foretinib. The preliminary structure-activity relationships as well as molecular docking disclosed that 1H-imidazole-4-carboxamido as a linker was of great importance for the antitumor activity.
- Wang, Xiaoqiang,Jiang, Nan,Zhao, Sijia,Xi, Shuancheng,Wang, Jiao,Jing, Tongfei,Zhang, Wenyu,Guo, Ming,Gong, Ping,Zhai, Xin
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p. 886 - 896
(2017/02/05)
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- A primary alcohol nitrile method (by machine translation)
-
The invention discloses a catalytic oxidation of primary alcohol nitrile method, said method comprising the following steps: formula (I) or formula (III) as shown in the primary alcohol as the raw material, in order to copper salt as catalyst, in order to air as the oxidizing agent, in order to TEMPO (2, 2, 6, 6 - tetramethyl piperidine nitrogen oxide) and help the oxidizing agent, ammonia as cocatalyst and solvent, for 80 - 120 °C reaction under 15 - 30h, after the reaction, the resulting reaction solution by the following formula (II) after treatment of the formula (IV) is shown in the nitriles; the reaction of the invention conversion, high yield, easy operation, low cost, safe reaction, the whole process is friendly to the environment, pollution-free. (by machine translation)
- -
-
Paragraph 0115; 0116; 0117; 0118; 0119
(2017/07/22)
-
- Copper (II)-catalysed direct conversion of aldehydes into nitriles in acetonitrile
-
A mild one-pot method for the direct conversion of aryl, heteroaryl and alkyl aldehydes into nitriles was achieved by forming the corresponding oximes in situ with NH2OH and allowing them to react with CuO and acetonitrile. Yields of the 13 nitriles prepared were moderate to very good (62–91%).
- Ma, Xiaoyun,Ao, Jun,Chen, Zhengjian,Liu, Yi
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p. 465 - 468
(2017/08/18)
-
- Half-Sandwich Guanidinate-Osmium(II) Complexes: Synthesis and Application in the Selective Dehydration of Aldoximes
-
The novel guanidinate-osmium(II) complexes [OsCl{κ2-(N,N′)-C(NR)(NiPr)NHiPr}(η6-p-cymene)] [R = Ph (3a), 4-C6H4F (3b), 4-C6H4Cl (3c), 4-C6H4CF3 (3d), 3-C6H4CF3 (3e), 3,5-C6H3(CF3)2 (3f), 4-C6H4CN (3g), 4-C6H4Me (3h), 3-C6H4Me (3i), 2-C6H4Me (3j), 4-C6H4tBu (3k), 2,6-C6H3iPr2 (3l), 2,4,6-C6H2Me3 (3m)] have been synthesized in high yields (70-88 %) by treatment of THF solutions of the dimeric precursor [{OsCl(μ-Cl)(η6-p-cymene)}2] (1) with 4 equivalents of the corresponding guanidine (iPrHN)2C=NR (2a-m) at room temperature. The easily separable guanidinium chloride salts [(iPrHN)2C(NHR)]Cl (4a-m) were also formed in these reactions. The structures of 3a, 3d, and 3h were unequivocally confirmed by X-ray diffraction methods. Complexes 3a-m proved to be active in the catalytic dehydration of aldoximes. The best results were obtained with [OsCl{κ2-(N,N′)-C(N-4-C6H4CF3)(NiPr)NHiPr}(η6-p-cymene)] (3d; 5 mol-%), which, in acetonitrile at 80C, was able to convert selectively a large variety of aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldoximes into the corresponding nitriles in high yields and short reaction times. Novel osmium(II)-guanidinate complexes of general composition [OsCl{κ2-(N,N′)-C(NR)(NiPr)NHiPr}(η6-p-cymene)] (R = Ar) have been synthesized and successfully employed as catalysts for the selective conversion of aldoximes into nitriles.
- Francos, Javier,González-Liste, Pedro J.,Menéndez-Rodríguez, Lucía,Crochet, Pascale,Cadierno, Victorio,Borge, Javier,Anti?olo, Antonio,Fernández-Galán, Rafael,Carrillo-Hermosilla, Fernando
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p. 393 - 402
(2016/02/03)
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- An efficient one-pot protocol for the conversion of benzaldehydes into tetrazole analogs
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An efficient protocol has been developed for the one-pot synthesis of tetrazole derivatives in moderate to good yields starting from substituted benzaldehydes and proceeding via non-isolated oxime and nitrile intermediates. The structures of the desired products were confirmed by IR, and NMR spectroscopy as well as mass spectrometry. A plausible reaction mechanism is also discussed.
- Khan, Khalid Mohammed,Fatima, Itrat,Saad, Syed Muhammad,Taha, Muhammad,Voelter, Wolfgang
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p. 523 - 524
(2016/01/20)
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- An efficient transformation of primary halides into nitriles through palladium-catalyzed hydrogen transfer reaction
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Two-step one-pot transformation of primary halides into corresponding nitriles is successfully achieved. Nucleophilic substitution of primary halides with sodium azide and subsequent palladium-catalyzed hydrogen transfer proceeds smoothly in the presence of sterically bulky ligand dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPhos) in acetone to produce nitriles in satisfactory to good yields. This journal is
- Zou, Tao,Yu, Xiaoqiang,Feng, Xiujuan,Bao, Ming
-
supporting information
p. 10714 - 10717
(2015/06/30)
-
- METHOD FOR PRODUCING NITRILE COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for producing a nitrile compound capable of obtaining a nitrile compound in a short time and at a low temperature, while maintaining a high yield. SOLUTION: There is provided a method for producing a nitrile compound using a compound having a hydroxymethylene group as a raw material. The nitrile compound is obtained by mixing and reacting an aliphatic compound or an aromatic compound having a hydroxymethylene group with a N-nitrosyl compound, an oxidant, an iodinating agent and ammonia water. COPYRIGHT: (C)2015,JPO&INPIT
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-
Paragraph 0041-0044; 0047
(2016/11/17)
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- Synthesis of aryl dihydrothiazol acyl shikonin ester derivatives as anticancer agents through microtubule stabilization
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The high incidence of cancer and the side effects of traditional anticancer drugs motivate the search for new and more effective anticancer drugs. In this study, we synthesized 17 kinds of aryl dihydrothiazol acyl shikonin ester derivatives and evaluated their anticancer activity through MTT assay. Among them, C13 showed better antiproliferation activity with IC50 = 3.14 ± 0.21 μM against HeLa cells than shikonin (IC50 = 5.75 ± 0.47 μM). We then performed PI staining assay, cell cycle distribution, and cell apoptosis analysis for C13 and found that it can cause cell arrest in G2/M phase, which leads to cell apoptosis. This derivative can also reduce the adhesive ability of HeLa cells. Docking simulation and confocal microscopy assay results further indicated that C13 could bind well to the tubulin at paclitaxel binding site, leading to tubulin polymerization and mitotic disruption.
- Lin, Hong-Yan,Li, Zi-Kang,Bai, Li-Fei,Baloch, Shahla Karim,Wang, Fang,Qiu, Han-Yue,Wang, Xue,Qi, Jin-Liang,Yang, Raong-Wu,Wang, Xiao-Ming,Yang, Yong-Hua
-
-
- Metal-free, one-pot oxidative conversion of aldehydes to primary thioamides in aqueous media
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One-pot tandem reactions of a variety of aldehydes with aqueous ammonia, molecular iodine, and O,O-diethyl dithiophosphoric acid readily afford the corresponding primary thioamides. This is an inexpensive, practical, and metal-free way of accessing various thioamides from aldehydes in aqueous media. The pure products are obtained simply by filtration followed by successive washing with aqueous sodium thiosulfate and water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
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supporting information
p. 408 - 416
(2014/01/06)
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- Conversion of aldoximes into nitriles catalyzed by simple transition metal salt of the fourth period in acetonitrile
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Conversion of aldoximes into nitriles catalyzed by simple transition metal catalysts, such as copper salts, nickel salts, cobalt salts, zinc salts, iron salts, and manganese salts in acetonitrile was investigated. All the metal salts display catalytic property in the conversion of aldoximes into nitriles and cupric acetate exhibits much higher activity than other catalysts. The corresponding amide was detected in almost all cases and acetonitrile was found to be involved in the conversion of aldoximes into nitriles.
- Ma, Xiao-Yun,He, Ying,Lu, Ting-Ting,Lu, Ming
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p. 2560 - 2564
(2013/03/28)
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- An efficient, rapid and facile procedure for conversion of aldoximes to nitriles using triphenylphosphine and N-halo sulfonamides
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N,N,N′,N′-Tetrabromobenzene-1,3-disulfonamide (TBBDA)/triphenylphosphine and N,N,N′,N′-tetrachlorobenzene-1,3- disulfonamide (TCBDA)/triphenylphosphine have been introduced as highly efficient systems for the versatile conversion of aldoxime derivatives into nitriles. The process reported here is operationally simple and reactions have been mildly performed in dichloromethane at room temperature.
- Ghorbani-Vaghei, Ramin,Shiri, Lotfi,Ghorbani-Choghamarani, Arash
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p. 1123 - 1126
(2014/01/06)
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- Molecular iodine in aqueous ammonia: Oxidative fragmentation of oxiranes to nitriles
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Oxiranes undergo oxidative fragmentation, when treated with iodine in aqueous ammonia, to give nitriles. The reaction goes via formation of 1,2-amino alcohols as intermediates followed by CC bond cleavage. Advantages of the method are use of off-the-shelf nonexplosive, unlike previously used potentially explosive o-iodoxybenzoic acid, reagents, mild reaction conditions, and easy work-up procedure.
- Jadhav, Ravindra R.,Akamanchi, Krishnacharya G.
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p. 162 - 164
(2013/03/28)
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- Cu(I)/TEMPO-catalyzed aerobic oxidative synthesis of imines directly from primary and secondary amines under ambient and neat conditions
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By catalyst and condition screening, a simple Cu(I)/TEMPO-catalyst system was found to be an active and highly effective catalyst for the aerobic oxidation of amines to imines in open air at room temperature under neat conditions. This new method provided a mild, efficient, and practical alternative for the synthesis of the useful imines directly from primary and secondary amines.
- Huang, Bo,Tian, Haiwen,Lin, Shoushuai,Xie, Meihua,Yu, Xiaochun,Xu, Qing
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supporting information
p. 2861 - 2864
(2013/06/05)
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- Simple one-pot conversion of alcohols into nitriles
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Various benzylic and primary alcohols were efficiently converted into the corresponding nitriles in good yields at room temperature by treatment with tert-butyl hypochlorite, diiodine, or 1,3-diiodo-5,5-dimethylhydantoin in the presence of (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl (TEMPO), followed by treatment with diiodine and aqueous ammonia. The nitriles were obtained in good yields and high purities simply by extraction of the reaction mixture with chloroform and subsequent removal of the solvent.
- Shimojo, Hiroyuki,Moriyama, Katsuhiko,Togo, Hideo
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p. 2155 - 2164
(2013/08/23)
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- Direct synthesis of nitriles from alcohols or aldehydes using H 5IO 6/KI in aqueous ammonia
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The oxidative conversion of alcohols or aldehydes to the corresponding nitriles in moderate to good yields was easily achieved by treatment of H 5IO6 and KI in aqueous NH3. This simple and one-pot system provides easy workup and separation of the product. Copyright
- Ghorbani-Choghamarani, Arash,Sardari, Sara,Zolfigol, Mohammad Ali,Hajjami, Maryam
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p. 52 - 58,7
(2020/08/24)
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- Cyclic aromatic analogues of the hendrickson reagent; NMR studies and electrophilic properties
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Two novel cyclic aromatic analogues of the Hendrickson POP reagent, 1,1,3,3-tetraphenyl-1,3-dihydro-2,1,3-benzoxadiphosphole-1,3-diium bis(trifluoromethanesulfinate) and bis(trifluoromethanesulfonate), have been readily prepared by the treatment of 1,2-bis(diphenylphosphino)benzene or 1,2-bis(diphenylphosphoryl)benzene, respectively, with trifluoromethanesulfonic anhydride in dichloromethane. 31P and 19F NMR studies indicated that while the latter complex is formed as the sole product, the former species was shown to be the predominant component in equilibrium with 1-(diphenylphosphino)-2-[diphenyl(trifluoromethylsulfonyloxy)phosphonio]benzene trifluoromethanesulfinate and 1,2-bis[diphenyl(trifluoromethylsulfonyloxy) phosphonio]benzene bis(trifluoromethanesulfinate). The dehydrating POP systems were exploited in the conversion of aldoximes into nitriles. The dehydration occurred rapidly at room temperature and produced high yields with a variety of alkyl- and arylaldoximes, tolerating a wide range of substrates and functional groups. Georg Thieme Verlag Stuttgart New York.
- Moussa, Ziad
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experimental part
p. 460 - 468
(2012/03/11)
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- A thiophosphoryl chloride assisted transformation of arylaldoximes to thioamides
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Primary benzothioamides were accessed from benzaldoximes (benzaldehyde oximes) via benzonitriles in a sequential tandem approach utilizing thiophosphoryl chloride as a dehydrating and thionating agent. Georg Thieme Verlag Stuttgart New York.
- Pandey, Lokesh Kumar,Pathak, Uma,Mathur, Sweta,Suryanarayana
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experimental part
p. 377 - 379
(2012/03/27)
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- A non-metal catalysed oxidation of primary azides to nitriles at ambient temperature
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A novel non-metal catalyzed oxidation of organic azides to nitriles under solvent-free conditions is presented employing catalytic amounts of KI, and DABCO in aq. TBHP at room temperature. This non-metal catalyzed oxidation of azides provides good selectivity as double and triple bonds were not oxidized under the present reaction conditions. The Royal Society of Chemistry 2012.
- Lamani, Manjunath,Devadig, Pradeep,Prabhu, Kandikere Ramaiah
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p. 2753 - 2759
(2012/11/07)
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- Microwave promoted rapid dehydration of aldoximes to nitriles using melamine-formaldehyde resin supported sulphuric acid in dry media
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A simple and convenient procedure for the synthesis of nitriles by dehydration of aldoxime using supported sulphuric acid on melamine-formaldehyde resin (MFR) under solvent-free condition has been developed. A variety of aromatic and aliphatic aldoximes were converted to the corresponding nitriles. The resin was recovered and reused for subsequent reactions.
- Rezaei, Ramin,Karami, Marzeih
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experimental part
p. 815 - 818
(2012/01/06)
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- Simple and efficient one-pot synthesis of nitriles from amides and oximes using in situ-generated burgess-type reagent
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The dehydration of aldoximes and amides, and oxidation of benzoin are accomplished in one-pot using in situ-generated Burgess-type reagent. Taylor & Francis Group, LLC.
- Rappai, John P.,Karthikeyan, Jayakumar,Prathapan, Sreedharan,Unnikrishnan, Perupparampil A.
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experimental part
p. 2601 - 2606
(2011/08/07)
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- Oxidative fragmentation of oxiranes to nitriles with hypervalent iodine(V) reagents in aqueous ammonia
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Oxiranes undergo oxidative fragmentation when treated with hypervalent iodine(V) reagents particularly o-iodoxybenzoic acid in aqueous ammonia to give nitriles. The reaction goes via the formation of 1, 2-amino alcohols as intermediates followed by C-C bond cleavage.
- Deshmukh, Swapnil S.,Huddar, Sameerana N.,Jadhav, Ravindra R.,Akamanchi, Krishnacharya G.
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experimental part
p. 4533 - 4536
(2011/09/20)
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- NMR Studies and electrophilic properties of triphenylphosphine-trifluoromethanesulfonic anhydride; a remarkable dehydrating reagent system for the conversion of aldoximes into nitriles
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NMR Studies on the reaction of triphenylphosphine with various amounts of triflic anhydride at 0 °C is described. The reagent structure resulting from mixing 1.3 equiv of Ph3P with Tf2O (1.0 mmol) has been established as an equilibrium mixture consisting mainly of triphenyl(trifluoromethylsulfonyloxy)phosphonium trifluoromethanesulfinate and the corresponding bis(triphenyl)oxodiphosphonium trifluoromethanesulfinate dimer. The electrophilic properties of the system have been exploited in the development of a mild method for converting aldoximes into nitriles. The dehydration occurs at 0 °C under very mild conditions by initial activation of the oxime oxygen, followed by treatment with a base and subsequent elimination of triphenylphosphine oxide. The substrate scope and functional group tolerance of this useful method are explored.
- Moussa, Ziad,Ahmed, Saleh A.,ElDouhaibi, Ahmad S.,Al-Raqa, Shaya Y.
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experimental part
p. 1826 - 1831
(2010/09/07)
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- Ammoxidation of 2,6-dichloro toluene - From first trials to pilot plant studies
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The scaling-up of the gas phase catalytic ammoxidation of 2,6-dichloro toluene (DCT) to 2,6-dichloro benzonitrile (DCBN) over a promoted vanadium phosphate (VPO) catalyst from first lab-scale experiments to pilot plant runs is reported. First experiments in a row of conversions of isomeric dichloro toluenes using simple, non-promoted VPO catalysts only show poor yield and selectivity. In particular, DCT ammoxidation is hindered due to bulky chlorine substituents probably preventing a sufficient interaction of the methyl group and lattice oxygen and/or N-containing surface species. Improved synthesis of VPO catalyst with the addition of promoters and γ-alumina or titania leads to significant increase in DCT conversion and DCBN yield. A Cr containing vanadyl pyrophosphate catalyst admixed with titania (anatase) showed conversion up to 97% with DCBN yields of ca. 80%. The same catalyst was also used for pilot plant runs, usually in the form of 5 mm × 3.5 mm shaped tablets that were prepared from a larger batch of solid synthesis. The scaling-up of the process using 100 ml of catalyst was investigated both by catalytic experiments and reactor simulations. The results showed that the temperature control will be crucial in scaling-up. Validation of simulation results with that of experimental results was also checked and a good agreement between measured and simulated results is observed.
- Martin,Kalevaru,Smejkal
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scheme or table
p. 275 - 279
(2011/01/04)
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- Environment friendly protocol for the synthesis of nitriles from aldehydes
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A rapid and eco-friendly one-pot protocol for the synthesis of nitriles has been developed by treating various araldehydes bearing electron withdrawing as well as electron donating groups with hydroxylamine hydrochloride in the presence of non-toxic, non-corrosive and reusable zinc oxide (ZnO) as the catalyst under solvent-free microwave irradiation. The present approach offers the advantages of a clean reaction, simple methodology, employing readily available catalyst, short reaction duration (1. min), high selectivity; and high yield (90-98%).
- Madhusudana Reddy,Pasha
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experimental part
p. 1025 - 1028
(2011/10/08)
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- Efficient and high-yielding protocol for the synthesis of nitriles from aldehydes
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An operationally simple and high-yielding procedure has been developed for the conversion of araldehydes into the corresponding nitriles using p-toluenesulfonic acid (p-TSA) (a mild catalyst) under microwave irradiation. The products are characterized by infrared spectral analysis and by comparison of the melting and boiling points with the reported values. Copyright
- Reddy, M. B. Madhusudana,Pasha
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experimental part
p. 3384 - 3389
(2010/12/25)
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- Zinc chloride-catalyzed expeditious route to nitriles
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Zinc chloride has been found to be an excellent catalyst for a one-pot synthesis of nitriles from araldehydes and hydroxylammonium chloride under solvent-free conditions. The features of the present method are short reaction time, easy workup procedure, and good yields of the nitriles.
- Paesha,Nizam, Aatika
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scheme or table
p. 1276 - 1279
(2010/06/20)
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- Microwave assisted, solvent free one pot synthesis of nitriles from aryl aldehydes on melamin formaldehyde as solid support
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Various aryl aldehydes underwent prompt one pot conversion into the corresponding nitriles in high yields by reacting with hydroxylamine hydrochloride supported on melamine formaldehyde under microwave irradiation in the presence of ammonium acetate as catalyst.
- Rezaei, Ramin,Mohammadi, Mohammad Kazem,Rastin, Nedaa
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scheme or table
p. 993 - 996
(2010/10/02)
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- Compostions and Methods for Controlling Nematodes
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Compositions and processes for controlling nematodes are described herein, e.g., nematodes that infest plants or animals. The compounds include oxazoles, oxadiazoles and thiadiazoles.
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Page/Page column 41
(2009/03/07)
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- Controlled conversion of phenylacetic acids to phenylacetonitriles or benzonitriles using bis(2-methoxyethyl)aminosulfur trifluoride
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A mild, efficient, and practical method for the one-step synthesis of benzonitriles from phenylacetic acids using bis(2-methoxyethyl)aminosulfur trifluoride is described. The reaction was easily extended to the synthesis of the corresponding phenylacetonitriles by inclusion of triethylphosphine.
- Kangani, Cyrous O.,Day, Billy W.,Kelley, David E.
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p. 914 - 918
(2008/09/17)
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- Hydrogen peroxide oxidation of N,N-dimethylhydrazones promoted by selenium compounds, titanosilicalites or acetonitrile
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Hydrogen peroxide oxidation of N,N-dimethylhydrazones 1 promoted by title reagents has been investigated. Depending on the substrate nitrile 2 and/or amide 3 accompanied with carboxylic acid 4 and parent carbonyl compounds 5 were obtained. Formation of nitriles 2 with H2O2-acetonitrile system is limited for a few more active substrates. The mechanism of the reaction, based on generated in situ peroxyiminoacetic acid, is presented. A broad spectrum of aliphatic, unsaturated and aromatic nitriles 2 was obtained by oxidation of corresponding N,N-dimethylhydrazones 1 with hydrogen peroxide in the presence of poly(bis-9,10-anthracenyl) diselenide (PADS) (7) as catalyst.
- Giurg,Mlochowski,Ambrozak
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p. 1713 - 1720
(2007/10/03)
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- TrocCl mediated efficient synthesis of nitriles from primary amides
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In order to establish a rapid conversion method of primary amides to nitriles, various types of carboxamides were treated with 2,2,2- trichloroethyl chloroformate and Et3N, as a dehydrating agent to obtain the desired nitriles in 82-95% yields.
- Bose, D. Subhas,Kumar, K. Kiran
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p. 3047 - 3052
(2007/10/03)
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- New NO donors with antithromobotic and vasodilating activities, part 27: Azide oximes and 1-hydroxytetrazoles
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Eleven azide oximes were prepared and tested for their antiplatelet (in vitro), antithrombotic, and blood pressure lowering activities. Nine of them inhibited the aggregation of blood platelets (Born test, inducer collagen) with IC50 values between 10 and 50 μM. The most active compounds i.e. azido-4-nitrophenylbenzaldoxime (2h) had an IC50 = 2 μM. Nine azide oximes exhibited significant antithrombotic properties. The most active compounds were 2h and 2c (azido-4-methylphenylbenzaldoxime) with an inhibition of thrombus formation above 20% in arterioles after a single p.o. dose of 60 mg/kg. Both compounds lowered the blood pressure in spontaneously hypertensive rats by 11% (2h) or 5% (2c), respectively. Seven azide oximes were rearranged to the title tetrazololes which however showed smaller antithrombotic effects. In separate in vitro experiments at 37 °C it could be demonstrated that azide oximes release nitric oxide (conversion rate ~ 10% · h-1) and nitrosohydrogen (conversion rate ~ 2% · h-1). This makes it appear probable that the above effects are mediated by these molecules.
- Rehse, Klaus,Brehme, Franziska
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p. 157 - 161
(2007/10/03)
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- Microwave-assisted methods for conversion of aldehydes into nitriles
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A rapid conversion of aldehydes to corresponding nitriles has been achieved under microwave irradiation using hydroxylamine and phthalic anhydride or hydroxylamine and Envirocatalyst EPZG(R) in solvent free conditions.
- Veverkova, Eva,Toma, Stefan
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p. 3109 - 3114
(2007/10/03)
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- Microwave activation in organic synthesis: Natural Indian clay, EPIC(R) EPZG(R) and EPZ10(R) as novel heterogenous catalysts for rapid synthesis of nitriles from aldoximes in absence of solvent
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The Conversion of aldoximes into nitriles was carried out in the absence of solvent under microwave irradiation using environmentally-friendly catalysts like natural kaolinitic clay, EPIC(R) EPZG(R) and EPZ10(R). Acceleration of reaction rate, simple work-up and formation of clean products are salient features of this method.
- Bandgar,Sadavarte,Sabu
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p. 3409 - 3413
(2007/10/03)
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- Dialkyltin oxide-catalyzed synthesis of nitriles from primary amides under neutral conditions
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A new and versatile method for the conversion of primary amides to nitriles in good yields using organostannyl oxides as catalytic neutral dehydrating agents is described.
- Bose, D. Subhas,Jayalakshmi,Goud, P. Ravinder
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p. 1724 - 1726
(2007/10/03)
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- A simple method for the synthesis of nitriles from primary amides under neutral conditions
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1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) is a very useful reagent for the preparation of nitriles in good yields under neutral conditions.
- Bose, D. Subhas,Sunder, K. Sugnana
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p. 4235 - 4239
(2007/10/03)
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- A direct synthesis of aromatic nitriles from methylaromatic compounds by ammoxidation on DC-108 catalyst
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Aromatic nitriles were prepared from corresponding methylaromatic compounds by ammoxidation on DC-108 catalyst, giving 51-89 percent in yield. This method is simple and convenient without pollution.
- Qiong, Zheng,Chi, Huang,Guangyong, Xie,Chongwen, Xu,Yuanyin, Chen
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p. 2349 - 2354
(2007/10/03)
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- Efficient one pot synthesis of nitriles from aldehydes in solid state using peroxymonosulfate on alumina
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In an environmentally benign solvent-free system, aldehydes are rapidly transformed into nitriles using peroxymonosulfate-alumina under microwave irradiation.
- Bose, D. Subhas,Narsaiah, A. Venkat
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p. 6533 - 6534
(2007/10/03)
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