- Unexpected Hydrogenation of C-C-Double Bonds with tert-Butyl Iodide
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Heating of 3-isobutylidene-2,5-diketopiperazines 1 or 4, maleinimide or 2,3-dichloro-5,6-dicyano-p-benzoquinone with tert-butyl iodide in toluene gave rise to hydrogenation of the conjugated C-C-double bond affording 3-isobutyldiketopiperazines 2(rac) and 3(rac), succinimide, or 2,3-dichloro-5,6-dicyanohydroquinone, respectively. Furthermore, an interesting N-O-migration of a benzoyl group as well as reductive aromatization to pyrazines 5 and 6, respectively, were observed.
- Jin, Shangde,Liebscher, Juergen
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- Photometric-Potentiometric Evaluation of the Hydrolysis Constants of N-Bromo Compounds
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The equilibrium concentrations of all reaction products emerging from the hydrolysis of N-bromo compounds in the presence of bromide and thereby also the hydrolysis constants (K1) have been calculated from the absorbance at 392.8 nm, the pH-value and the initial concentrations of the N-bromo compound and the bromide.The following compounds have been investigated: N-bromo-succinimide: K1 = 2.2E-6, 1,3-dibromo-5,5-dimethylhydantoin: K1 = 1.7E-5, N-bromoacetamide: K1 = 1.8E-6, N-bromo-monochloroacetamide: 5.2E-6, N-bromo-dichloroacetamide: K1 = 8.9E-6 and N-bromo-trichloroacetamide: K1 = 1.8E-5.The precision of the method, which is mainly suited for weak hydrolizing N-bromocompounds (K15-12percent.The reactivities in aqueous solution of the most frequently used N-bromo compounds are compared by means of the calculated HOBr equilibrium concentrations.The differences to be expected on the basis of the latters are at concentrations >1E-5 mol/l rather great, while they can be neglected in very dilute solutions (/=1E-6 mol/l).Keywords: Disinfection; Equilibrium concentrations; N-Halogene compounds; Hydrolysis; Reactivity of N-bromo compounds.
- Gottardi, Waldemar
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- Electrochemical Reduction of N-Bromosuccinimide. Reaction Mechanism for Formation of the Succinimidyl Radical
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The electrochemical reduction of N-bromosuccinimide in acetonitrile at a platinum cathode generates the succinimidyl radica;l in an overall process for which the n value is 1.The succinimide anion, generated by two-electron reduction of N-bromosucinimide, is an intermediate in this process, and its electron-transfer reaction with the N-bromo imide generates the radical.The intermediacy of the succinimide anion is demonstrated by trapping experiments in which the anion is captured by alkylating agents to give N-alkylsuccinimides.With increasing capture of the anion the n value for the electrochemical reaction approaches 2 as a limit.The reduction of N-bromosuccinimide by the succinimide anion, added as a quaternary ammonium succinimide, in a purely chemical system has also been studied.Rate constants for the pertinent reactions have been measured, and the reaction mechanisms have been discussed.
- Barry, John E.,Finkelstein, Manuel,Moore, W. Michael,Ross, Sydney D.,Eberson, Lennart,Joensson, Lennart
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- Synthesis, characterization and cytotoxic studies of novel 1,2,4-triazole-azomethine conjugates
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Abstract: A series of 1,2,4-triazole-schiff hybrids were synthesized and characterized by mass spectrometry, FTIR and NMR spectroscopy. The compounds were screened for anticancer activity against human breast cancer cell line (MCF-7 and T47D) and human cervical cancer cell line (HeLa). The result indicates that newly synthesized compounds exhibit cytotoxicity to all cell lines studied. In particular, MCF-7 cells were shown to be more sensitive with EC50 50 13.10?μM/ml. To further investigate the mode of cell death, early and late apoptosis studies were done on MCF-7 cells. The externalization of phosphatidylserine and DNA fragmentation supports the apoptosis as the major mode of cell death induced by derivatives on MCF-7 cells. Graphic abstract: [Figure not available: see fulltext.]
- Mahar, Jamaluddin,Saeed, Aamer,Chaudhry, Gul-e-Saba,Irfan, Madiha,Channar, Pervaiz Ali,Faisal, Muhammad,Larik, Fayaz Ali
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- Photodecomposition of N-Bromosuccinimide: Radical Chain Carriers and Their Interrelations
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The direct photolysis of N-bromosuccinimide (NBS) in the absence and presence of bromine and its bromine atom initiated decomposition were investigated by selective irradiation of NBS or Br2 and by critically examining the β-bromopropionyl isocyanate (BPI) yields and the relative selectivity of intermolecular H abstraction from cyclohexane and CH2Cl2.Experimental results showed (i) that direct photolysis of NBS gave extra amounts of BPI, (ii) that the bromine atom initiated NBS decomposition also generated BPI, and (iii) that the interaction of bromine atoms with NBS or the succinimidyl radical with bromine set up a rapid equilibrium of the radicals.In the NBS + Br2 system the relative selectivities of intermolecular H abstraction, kC6H12/kCH2Cl2, were 16-22, practically the same as those for a bromine atom (15-18), and the BPI percent yields decreased systematically as both initial and observed bromine concentrations increased in the range of 1-100 mM.Therefore, the photodecomposition of the NBS + Br2 system involves the succinimidyl radical and bromine atom in a fast equilibrium and as the radical-propagating species, without the need to invoke another radical.The succinimidyl radical generated from direct photolysis of NBS is proposed to be a vibrationally excited hot species that undergoes much faster ring opening than the ground-state species.These results provide a satisfactory explanation to resolve the most recent controversy over the number of radical intermediates involved in the NBS photodecomposition.
- Chow, Yuan L.,Zhao, Da-Chuan
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- One-Electron Reduction Potential and Ring Opening of the Succinimidyl Radical in Water
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By means of pulse radiolysis in water, N-chlorosuccinimide (SCl) was reduced in a one-electron step to yield the succinimidyl radicals, S*, via the intermediacy of the radical anion, SCl*-.The rate of ring opening of S* was measured to be 8 x 104 s-1.By equilibrium with Cl2*-/2Cl-, the one-electron reduction potential of S* was determined to be 2.22 +/- 0.02 V vs NHE.From this value and other data, the N-H bond strength in succinimide was calculated to be 118 +/- 3 kcal/mol.
- Lind, Johan,Jonsson, Mats,Eriksen, Trygve E.,Merenyi, Gabor,Eberson, Lennart
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- Kinetics and mechanism of the reaction of N-chlorosuccinimide with I - and OH-
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In this kinetic study of the reaction between the iodide ion and the N-chlorosuccinimide, we have found that the reaction is first order in N-chlorosuccinimide: namely, first order with respect to the iodide ion and first order with respect to the proton concentration. Based on the experimental results, we propose a mechanism consistent in Cl+ transfer from the N-chlorosuccinimide to the iodide ion. We have found that the reaction presents general acid catalysis with a Broensted exponent value of 0.10. In addition, given that the N-chlorocompounds are not stable in aqueous solution, we have carried out a study on the influence of bases in the presence of N-chlorosuccinimide. We have found that the reaction is first order in hydroxide ion, as well as in the 1,1,1,3,3,3-hexafluoroisopropanoxide ion and the 2,2,2-trifluorethoxide ion. which shows that the reaction is general-base catalyzed.
- Agulla,Antelo,Arce,Parajo
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- Polarographic determination of vitamin C after derivatization with o-phenylenediamine
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A differential pulse polarographic (DPP) method has been developed for the determination of ascorbic acid (AA) and dehydroascorbic acid (DHA), the two main forms of Vitamin C. The method consists of the DPP analysis of a quinoxaline obtained by the derivatization of DHA with o-phenylenediamine. Results using the proposed method correlated well with those obtained by two reference methodologies: the common iodometric method and a published chromatographic methodology. It was also used in the study of Vitamin C degradation in fruit juices, showing that it involves an initial oxidation of AA to DHA, followed by ydrolytic degradation of the latter.
- Rodrigues, Jose Antonio,Valente, Ines Maria,Goncalves, Luis Moreira,Pacheco, Joao Grosso,Barros, Aquiles Araujo
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- Kinetics of radical-initiated chain bromination of 2-methyl-2-propanol by N-bromosuccinimide in water
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The kinetics and product distribution of the radical chain bromination of 2-methyl-2-propanol (RH) by N-bromosuccinimide (SBr) in water have been studied by pulse-radiolytic and γ-radiolytic methods in order to obtain key data for the reactivity of the succinimidyl radical, S?. The products of the reaction after γ-radiolysis are dependent on the concentration of RH, being essentially made up of equal amounts of (CH3)2C(OH)CH2Br and succinimide at [RH] > 0.5 M, while the hydrolyzed ring-opened product, 3-bromopropionamide, increases at the expense of (CH3)2C(OH)CH2Br when the RH concentration is lowered. The chain-propagating steps R? + SBr → RBr + S? (i) and S? + RH → SH + R? (ii) of the S? mediated chain reaction had rate constants ki = (1.8 ± 0.3) × 108 (determined in three ways) and kii = (1 ± 0.5) × 107 M-1 s-1 (determined in four ways), respectively, whereas the corresponding rate constants for the Br? mediated chain under the same conditions were 2.5 × 109 and (5 ± 3) × 103 M-1 s-1. Under pulsed conditions with initial radical concentrations around 10-4 M, the chain length is ≈10. The ratio between kii and the rate constant for ring opening of S?, kiii (S? → ?CH2CH2CONCO), was determined to be 77 M-1, significantly higher than the corresponding value with neopentane as substrate and with dichloromethane as solvent (0.10 M-1). The kii value places S? as having significantly lower reactivity than OH? in hydrogen atom abstraction reactions, whereas a theoretical estimate based on electron affinities puts it in between Cl? and OH?, i.e. at higher reactivity than OH?. This provides kinetic evidence for the II nature of ground state S?. It was also established that Br? complexes rather strongly to SBr according to SBr + Br? → SBr2? (iv). As kiv = (4-7) × 103 M-1 and SBr2? is probably unreactive, the propagation rate of a bromine atom chain is expected to decrease with increasing SBr concentration.
- Lind, Johan,Jonsson, Mats,Xinhua, Shen,Eriksen, Trygve E.,Merényi, Gábor,Eberson, Lennart
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- Mechanism of Photoredox-Initiated C-C and C-N Bond Formation by Arylation of IPrAu(I)-CF3 and IPrAu(I)-Succinimide
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Herein, we report on the photoredox-initiated gold-mediated C(sp2)-CF3 and C(sp2)-N coupling reactions. By adopting gold as a platform for probing metallaphotoredox catalysis, we demonstrate that cationic gold(III) complexes are the key intermediates of the C-C and C-N coupling reactions. The high-valent gold(III) intermediates are accessed by virtue of photoredox catalysis through a radical chain process. In addition, the bond-forming step of the coupling reactions is the reductive elimination from cationic gold(III) intermediates, which is supported by isolation and crystallographic characterization of key Au(III) intermediates.
- Kim, Suhong,Toste, F. Dean
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- Grinding imidation of anhydrides on smectite clays as recyclable and heterogeneous catalysts under solvent-free conditions
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Imidation of various anhydrides employing solvent-free grindstone technique using smectite clays as recyclable and green catalysts was examined and obtained excellent yields.
- Marvi, Omid
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- Synthesis of biobased succinimide from glutamic acid via silver-catalyzed decarboxylation
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Glutamic acid was transformed into succinimide in a two step procedure involving a dehydration in water to pyroglutamic acid followed by an oxidative decarboxylation using a silver catalyst.
- Deng, Jin,Zhang, Qiu-Ge,Pan, Tao,Xu, Qing,Guo, Qing-Xiang,Fu, Yao
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- Synthesis, physicochemical, and anticonvulsant properties of new N-Mannich bases derived from pyrrolidine-2,5-dione and its 3-methyl analog
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A series of 22 new N-[(4-phenylpiperazin-1-yl)-methyl]-3-methyl-pyrrolidine-2,5-dione and pyrrolidine-2,5-dione derivatives were synthesized and evaluated for their anticonvulsant activities in the maximum electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) seizure tests after intraperitoneal injection into mice. The neurotoxicity was determined applying the rotarod test. The in vivo results in mice showed that seven compounds were effective in the MES or/and scPTZ seizure tests. The quantitative evaluation in both tests after i.p. administration into mice revealed that the most active compounds were N-[{4-(3,4-dichlorophenyl)-piperazin-1-yl}-methyl]-3-methylpyrrolidine-2,5-dione (12) with ED50 = 16.13 mg/kg (MES), ED50 = 133.99 mg/kg (scPTZ) and N-[{4-(3,4-dichlorophenyl)-piperazin-1-yl}-methyl]-pyrrolidine-2,5-dione (23) with ED50 = 37.79 mg/kg (MES), ED50 = 128.82 mg/kg (scPTZ), whereas N-[{4-(3-trifluoromethylphenyl)-piperazin-1-yl}-methyl]-pyrrolidine-2,5-dione (24) was effective only in the MES test with ED50 = 16.37 mg/kg. These molecules showed higher potency and also lower neurotoxicity than the reference antiepileptic drugs such as ethosuximide and valproic acid. New N-[(4-phenylpiperazin-1-yl)-methyl]-3-methyl-pyrrolidine-2,5-dione and pyrrolidine-2,5-dione derivatives were evaluated for their anticonvulsant activities and neurotoxicities. The most active compounds were N-[{4-(3,4-dichlorophenyl)-piperazin-1-yl}-methyl]-3-methylpyrrolidine-2,5-dione and N-[{4-(3,4-dichlorophenyl)-piperazin-1-yl}-methyl]-pyrrolidine-2,5-dione with ED50 values of 16.13 and 37.79 mg/kg in the maximal electroshock test, respectively.
- Rybka, Sabina,Obniska, Jolanta,Rapacz, Anna,Filipek, Barbara,Kamiński, Krzysztof
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- N -Iodosuccinimide-Promoted Selective Construction of Cyclopropyl and Dihydrofuranyl Spirooxindoles from Alkylidene Oxindoles and Annular β-Dicarbonyl Compounds
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An efficient N-iodosuccinimide-promoted cyclization of readily available alkylidene oxindoles with annular β-dicarbonyl compounds has been demonstrated. With five-membered cyclic β-dicarbonyl compounds as the starting materials, a series of cyclopropyl oxindoles can be obtained in good to excellent yields, whereas the method affords dihydrofuranyl spirooxindoles almost quantitatively when six- or seven-membered cyclic β-dicarbonyl compounds are employed. This protocol provides a new alternative to the practical synthesis of structurally diverse spirooxindoles.
- Chen, Hong,He, Zeng-Yang,Huang, Fei-Hong,Jin, Ying,Xu, Hui,Zhang, Ze,Zou, Peng
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supporting information
(2022/03/08)
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- Nucleophilic Substitution at the Guanidine Carbon Center via Guanidine Cyclic Diimide Activation
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Despite the electron-deficient nature of the guanidine carbon centers, nucleophilic reactions at these sites have been underdeveloped because of the resonance stabilization of the guanidine group. We propose a guanidine C-N bond substitution strategy entailing the formation of guanidine cyclic diimide (GCDI) structures, which effectively destabilize the resonance structure of the guanidine group. In the presence of acid additives, the guanidine carbon center of GCDIs undergoes nucleophilic substitution reactions with various amines and alcohols.
- An, Taeyang,Lee, Yan
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supporting information
p. 9163 - 9167
(2021/11/24)
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- Method for preparing diloxitol fumarate
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The invention relates to the technical field of a bulk drug preparation method and in particular relates to a method for preparing a bulk drug diloxitol fumarate. The preparation method comprises thefollowing steps: 1) performing an ammoniation reaction, namely enabling succinic anhydride to react with an ammoniating reagent so as to produce succinimide; 2) performing an alkylation reaction, namely enabling succinimide to react with 1,2 halogenated ethane in the presence of a catalyst and a base so as to generate a compound of a formula IV shown in the description; and 3) performing an esterification reaction, namely enabling a compound of a formula IV compound shown in the description to react with trans-monomethyl fumarate, so as to generate diloxifyl fumarate. The method has the advantages that material reagents used in the method are convenient and easy to obtain, the reaction steps are short, the total yield is high, the product is easy to purify through recrystallization, and base toxic impurities are easy to be controlled through recrystallization, and the like.
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Paragraph 0072-0074; 0081-0083; 0088-0090; 0095-0097
(2020/02/14)
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- Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration
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A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).
- Wang, Yong,Cao, Xinyi,Zhao, Leyao,Pi, Chao,Ji, Jingfei,Cui, Xiuling,Wu, Yangjie
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supporting information
p. 4119 - 4129
(2020/08/10)
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- Hydrogenation reaction method
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The invention relates to a hydrogenation reaction method, and belongs to the technical field of organic synthesis. The hydrogenation reaction method provided by the invention comprises the following steps: carrying out a hydrogen transfer reaction on a hydrogen acceptor compound, pinacol borane and a catalyst in a solvent in the presence of proton hydrogen, so that the hydrogen acceptor compound is subjected to a hydrogenation reaction; the catalyst is one or more than two of a palladium catalyst, an iridium catalyst and a rhodium catalyst; the hydrogen acceptor compound comprises one or morethan two functional groups of carbon-carbon double bonds, carbon-carbon triple bonds, carbon-oxygen double bonds, carbon-nitrogen double bonds, nitrogen-nitrogen double bonds, nitryl, carbon-nitrogentriple bonds and epoxy. The method is mild in reaction condition, easy to operate, high in yield, short in reaction time, wide in substrate application range, suitable for carbon-carbon double bonds,carbon-carbon triple bonds, carbon-oxygen double bonds, carbon-nitrogen double bonds, nitrogen-nitrogen double bonds, nitryl, carbon-nitrogen triple bonds and epoxy functional groups, good in selectivity and high in reaction specificity.
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Paragraph 0034; 0109-0112
(2020/05/14)
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- Synthesis of N-unsubstituted cyclic imides from anhydride with urea in deep eutectic solvent (DES) choline chloride/urea
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N-Unsubstituted cyclic imides were readily synthesized in deep eutectic solvent (DES) choline chloride (ChCl)/urea from anhydrides with urea. Urea serves as both a DES component and a nitrogen source, which endows the protocol with advantages of smooth reaction, easy separation of products, simple recovery and recycling of ChCl/urea.
- Liu, Luxiao,Zhang, Hong-Yu,Yin, Guohui,Zhang, Yuecheng,Zhao, Jiquan
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p. 1351 - 1357
(2019/11/19)
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- Catalyst and Additive-Free Direct Amidation/Halogenation of Tertiary Arylamines with N-haloimide/amides
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An approach has been developed for the amidation (halogenation) of tertiary arylamines by electrophilic activation using N-haloimide/amides. Several control experiments have been performed, and the coupling reaction outcomes indicated that the N-haloimide/amide brings three major functions, including electrophilic activation, aromatic halogenation and nucleophilic nitrogen sources. This cascade reaction features simple manipulation, requires no additional catalyst, oxidant or additives, and is performed under mild conditions. (Figure presented.).
- Xu, Xiu-Juan,Amuti, Adila,Wusiman, Abudureheman
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supporting information
p. 5002 - 5008
(2020/10/06)
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- Method for catalytically oxidizing amine to be synthesized into amide through dipyridyl-type manganese catalyst
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The invention discloses a methodfor catalytically oxidizing amine to be synthesized into amide througha dipyridyl-type manganese catalyst. According to the method, a dipyridyl manganese complex formedafter coordination of a dipyridyl-type complex and cheap metal manganese serves as the catalyst, clean and environment-friendly hydrogen peroxide serves as an oxidizing agent, oxidation of N ortho-position sp3 C-H bonds catalyzed by the cheap metal manganese is achieved, and the amine is directly oxidized to obtain the amide. Compared with existing methods, the method has the advantages that theadopted catalyst is low in price, the preparing method is simple, raw materials are easy to obtain, the use level of the catalyst is low, the substrate range is wide, the reaction condition is mild, the operation is simple and environmentally friendly, the reaction time is short, the yield is high, the selectivity is high, and the industrialization cost is low.
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Paragraph 0017-0030
(2019/06/30)
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- Dual Stereocontrol for Enantioselective Hydrogenation of Dihydroisoquinolines Induced by Tuning the Amount of N-Bromosuccinimide
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An efficient dual stereocontrol in iridium-catalyzed hydrogenation of 1-substituted 3,4-dihydroisoquinolines was realized by tuning the amount of N-bromosuccinimide using chiral ligand of single configuration, providing both enantiomers of 1-substituted 1,2,3,4-tetrahydroisoquinolines with up to 89% ee (S) and 98% ee (R), respectively. Dual activation role of N-bromosuccinimide is proposed to be responsible for the reversal of enantioselectivity under two hydrogenation conditions.
- Ji, Yue,Wang, Jie,Chen, Muwang,Shi, Lei,Zhou, Yonggui
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supporting information
p. 139 - 142
(2018/01/05)
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- Esterification of aryl/alkyl acids catalysed by n-bromosuccinimide under mild reaction conditions
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N-halosuccinimides (NXSs) are well-known to be convenient, easily manipulable and low-priced halogenation reagents in organic synthesis. In the present work, N-bromosuccinimide (NBS) has been promoted as the most efficient and selective catalyst among the NXSs in the reaction of direct esterification of aryl and alkyl carboxylic acids. Comprehensive esterification of substituted benzoic acids, mono-, di- and tri-carboxy alkyl derivatives has been performed under neat reaction conditions. The method is metal-free, air- and moisture-tolerant, allowing for a simple synthetic and isolation procedure as well as the large-scale synthesis of aromatic and alkyl esters with yields up to 100%. Protocol for the recycling of the catalyst has been proposed.
- ?ebular, Klara,Bo?i?, Bojan ?.,Stavber, Stojan
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- Synthesis and evaluation of anticonvulsant properties of new N-Mannich bases derived from pyrrolidine-2,5-dione and its 3-methyl-, 3-isopropyl, and 3-benzhydryl analogs
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The aim of this paper was to describe the synthesis of a library of 28 new 1,3-substituted pyrrolidine-2,5-dione as potential anticonvulsant agents. The anticonvulsant activity was evaluated using three acute models of seizures in mice (MES-maximal electroshock, scPTZ-subcutaneous pentylenetetrazole, and 6?Hz-psychomotor seizure tests). The neurotoxicity was determined by rotarod test. The most promising compound was found to be N-[{morpholin-1-yl}-methyl]-3-benzhydryl-pyrrolidine-2,5-dione (15), as it was active in the MES (ED50?=?41.0?mg/kg), scPTZ (ED50?=?101.6?kg/mg), and 6?Hz (ED50?=?45.42?mg/kg) tests. This compound displayed more beneficial protection index (PI) than antiepileptic drugs such as ethosuximide, lacosamide and valproic acid. In vitro studies for compound 15 were conducted and provided information that its possible mechanism of action is related to blocking of the neuronal voltage-sensitive sodium (site 2) and L-type calcium channels.
- Rybka, Sabina,Obniska, Jolanta,Rapacz, Anna,Filipek, Barbara,?mudzki, Pawe?
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supporting information
p. 1412 - 1415
(2017/03/08)
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- Heterolytic (2 e) vs Homolytic (1 e) Oxidation Reactivity: N?H versus C?H Switch in the Oxidation of Lactams by Dioxirans
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Dioxiranes are powerful oxidants that can act via two different mechanisms: 1) homolytic (H abstraction and oxygen rebound) and 2) heterolytic (electrophilic oxidation). So far, it has been reported that the nature of the substrate dictates the reaction mode independently from the dioxirane employed. Herein, we report an unprecedented case in which the nature of the dioxirane rules the oxidation chemoselectivity. In particular, a switch from C?H to N?H oxidation is observed in the oxidation of lactams moving from dimethyl dioxirane (DDO) to methyl(trifluoromethyl)dioxirane (TFDO). A physical organic chemistry study, which combines the oxidation with two other dioxiranes methyl(fluoromethyl)dioxirane, MFDO, and methyl(difluoromethyl)dioxirane, DFDO, with computational studies, points to a diverse ability of the dioxiranes to either stabilize the homo or the heterolytic pathway.
- Annese, Cosimo,D'Accolti, Lucia,Fusco, Caterina,Licini, Giulia,Zonta, Cristiano
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supporting information
p. 259 - 262
(2017/01/17)
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- Strong influence of intramolecular Si?O proximity on reactivity: Systematic molecular structure, solvolysis, and mechanistic study of cyclic N-trimethylsilyl carboxamide derivatives
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A comparative alcoholysis study of N-silylated derivatives of simple heterocyclic carboxamides (lactams, imides, ureas) is presented. The second-order rate constant values span a range as wide as three orders of magnitude. On the basis of DFT calculations, a good correlation between reactivity and the Si?O distance was found within each family of compounds. The viability of two different reaction pathways was evaluated using a detailed computational mechanistic study of the methanolysis of cyclic urea homologues. Peculiarities in the single-crystal X-ray diffraction structures of the trimethylsilyl and trimethylsiloxy phthalimides are also discussed.
- Szalay, Roland,Harmat, Veronika,E?ri, János,Pongor, Gábor
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p. 2186 - 2192
(2017/05/16)
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- Asymmetric Hydrogenation of Isoquinolines and Pyridines Using Hydrogen Halide Generated in Situ as Activator
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By employing halogenide trichloroisocyanuric acid as a traceless activation reagent, a general iridium-catalyzed asymmetric hydrogenation of isoquinolines and pyridines is developed with up to 99% ee. This method avoids tedious steps of installation and removal of the activating groups. The mechanism studies indicated that hydrogen halide generated in situ acted as an activator of isoquinolines and pyridines.
- Chen, Mu-Wang,Ji, Yue,Wang, Jie,Chen, Qing-An,Shi, Lei,Zhou, Yong-Gui
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supporting information
p. 4988 - 4991
(2017/09/23)
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- Vanadium(v) oxoanions in basic water solution: A simple oxidative system for the one pot selective conversion of l-proline to pyrroline-2-carboxylate
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The unprecedented, direct chemical oxidation of l-proline to pyrroline-2-carboxylate was achieved in water (pH 9-10) by means of NH4VO3/NH3 or V2O5/MOH (K = Na, K), and the anion was fully characterized as ammonium or alkaline metal salts. Quantitative yield and higher atom economy performance were achieved with the latter system, the alkaline salts being more stable than the ammonium one. Different mixed valence V(iv)/V(v) compounds precipitated from the reaction mixtures depending on the nature of the employed base. A possible reaction mechanism is proposed according to DFT calculations. The analogous reaction of trans-4-hydroxy-l-proline with NH4VO3/NH3 afforded pyrrole-2-carboxylic acid in 81% yield, while sarcosine underwent prevalent decomposition under similar experimental conditions. Instead, no reaction was observed with primary (glycine, l-alanine, l-phenylalanine) and tertiary α-amino acids (N,N-dimethyl-l-phenylalanine, N,N-dimethylglycine).
- Biancalana, Lorenzo,Tuci, Giada,Piccinelli, Fabio,Marchetti, Fabio,Bortoluzzi, Marco,Pampaloni, Guido
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p. 15059 - 15069
(2017/11/14)
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- Direct Synthesis of Cyclic Imides from Carboxylic Anhydrides and Amines by Nb2O5 as a Water-Tolerant Lewis Acid Catalyst
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In the 20 types of heterogeneous and homogenous catalysts screened, Nb2O5 showed the highest activity for the synthesis of N-phenylsuccinimide by dehydrative condensation of succinic anhydride and aniline. Nb2O5 was used in the direct imidation of a wide range of carboxylic anhydrides with NH3 or amines with various functional groups and could be reused. Kinetic studies showed that the Lewis acid Nb2O5 catalyst was more water tolerant than both the Lewis acidic oxide TiO2 and the homogeneous Lewis acid ZrCl4, which resulted in higher yields of imides through the use of Nb2O5. Int-imidation tactics: A general method for the direct synthesis of cyclic imides from cyclic anhydrides with amines (or ammonia) under solvent-free conditions is reported. Kinetic studies indicate that the Lewis acid sites of Nb2O5 are highly water tolerant, which results in high catalytic activity for imidation even in the presence of water formed during the reaction. The catalyst can be recovered and reused four times without a marked decrease in yield.
- Ali, Md. A.,Moromi, Sondomoyee K.,Touchy, Abeda S.,Shimizu, Ken-Ichi
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p. 891 - 894
(2016/03/15)
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- An Efficient One-Pot Synthesis of Bis Butenolides
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3,3′,4,4′-Tetramethyl-5,5′-dioxo-2,2′-bifuran-2,2′(5H,5′H) diyl diacetate was obtained from the reaction between 2,3-dimethyl maleic anhydride and acetic anhydride in the presence of zinc in toluene. This easy synthetic route gave bis butenolide in excellent yield.
- Bayat, Mohammad,Fox, Joseph M.
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p. 1661 - 1664
(2016/09/23)
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- A method for preparing butanediimide (by machine translation)
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The present invention provides a method for preparing butanediimide, including: in the pyroglutamic acid and burnt glutanic acid salt of one or two, with an aqueous solution of a silver salt, persulfate mixed, succinimide obtained after the reaction. In this application in the process of preparing butanediimide, to pyroglutamic acid or burnt glutanic acid salt as raw materials, using the nitrogen source for the amino acid itself, avoid the corrosion resistance caused by the additional nitrogen source, therefore the mild condition of the preparation butanediimide; and this application uses wide raw material sources, the only role of silver salts and persulphate butanediimide can be obtained, therefore the preparation method is simple. (by machine translation)
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Paragraph 0036-0041
(2017/03/17)
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- Chemo- And diastereoselectivities in the electrochemical reduction of maleimides
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The electrochemical cathodic reduction of cyclic imides (maleimides) to succinimides can be achieved chemoselectively in the presence of alkene, alkyne, and benzyl groups. The efficiency of the system was demonstrated by using a 3D electrode in a continuous flow reactor. The reduction of 3,4-dimethylmaleimides to the corresponding succinimides proceeds with a 3:2 diastereomeric ratio, which is independent of the nitrogen substituent and electrode surface area. The stereoselectivity of the process was rationalized by using DFT calculations, involving an acid-catalyzed tautomerization of a half-enol occurring through a double hydrogen-transfer mechanism.
- Rix, Kathryn,Kelsall, Geoffrey H.,Hellgardt, Klaus,Hii, King Kuok
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p. 665 - 671
(2015/03/04)
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- BICYCLIC AZA COMPOUNDS AS MUSCARINIC M1 RECEPTOR AGONISTS.
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This invention relates to compounds that are agonists of the muscarinic M1 receptor and/or M4 receptor and which are useful in the treatment of muscarinic M1/M4 receptor mediated diseases. Also provided are pharmaceutical compositions containing the compounds and the therapeutic uses of the compounds. Compounds include those according to formula 1, or a salt thereof, wherein Q, R1 , R2, R3 and R4 are as defined herein.
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Page/Page column 64
(2015/09/22)
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- Hydrogenations without hydrogen: Titania photocatalyzed reductions of maleimides and aldehydes
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A mild procedure for the reduction of electron-deficient alkenes and carbonyl compounds is described. UVA irradiations of substituted maleimides with dispersions of titania (Aeroxide P25) in methanol/acetonitrile (1:9) solvent under dry anoxic conditions led to hydrogenation and production of the corresponding succinimides. Aromatic and heteroaromatic aldehydes were reduced to primary alcohols in similar titania photocatalyzed reactions. A mechanism is proposed which involves two proton-coupled electron transfers to the substrates at the titania surface.
- Manley, David W.,Buzzetti, Luca,MacKessack-Leitch, Andrew,Walton, John C.
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p. 15324 - 15338
(2015/01/16)
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- Identification, characterization, and application of three enoate reductases from Pseudomonas putida in in vitro enzyme cascade reactions
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Enoate reductases are versatile enzymes for the enantio- and regioselective addition of hydrogen to double bonds. We identified three EREDs (XenA, XenB, NemA) from Pseudomonas putida ATCC 17453 through a sequence motif search. In addition to cloning, functional expression, and biochemical characterization of these enzymes, the enoate reductases were also applied in enzyme cascade reactions in combination with a Baeyer-Villiger monooxygenase and an alcohol dehydrogenase to produce lactones. Good things come in threes: The identification, cloning, expression, and characterization of three enoate reductases from Pseudomonas putida reveal broad substrate scope and high stereoselectivities. Furthermore, the enoate reductases could be integrated into cascade reactions together with an alcohol dehydrogenase and a Baeyer-Villiger monooxygenase.
- Peters, Christin,Koelzsch, Regina,Kadow, Maria,Skalden, Lilly,Rudroff, Florian,Mihovilovic, Marko D.,Bornscheuer, Uwe T.
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p. 1021 - 1027
(2014/05/06)
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- Tosvinyl and besvinyl as protecting groups of imides, azinones, nucleosides, sultams, and lactams. Catalytic conjugate additions to tosylacetylene
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The use of the 2-(4-methylphenylsulfonyl)-ethenyl (tosvinyl, Tsv) group for the protection of the NH group of a series of imides, azinones (including AZT), inosines, and cyclic sulfonamides has been examined. The Tsvprotected derivatives are obtained in excellent yields by conjugate addition to tosylacetylene (ethynyl p-tolyl sulfone). The stereochemistry of the double bond can be controlled at will: with only 1 mol % of Et3N or with catalytic amounts of NaH, the Z stereoisomers are generated almost exclusively, while the E isomers are obtained using a stoichiometric amount of DMAP. Analogous phenylsulfonylvinyl-protected groups (with the besvinyl or Bsv group instead of Tsv) are obtained stereospecifically by reaction with (Z)- or (E)-bis(phenylsulfonyl)ethene. For lactams and oxazolidinones, this last method is much better. The Tsv and Bsv groups are stable in the presence of non-nucleophilic bases and to acids. They can be removed highly effectively via a conjugate addition-elimination mechanism using pyrrolidine or sodium dodecanethiolate as nucleophiles.
- Petit, Elena,Bosch, Llus,Font, Joan,Mola, Laura,Costa, Anna M.,Vilarrasa, Jaume
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p. 8826 - 8834
(2015/01/08)
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- Nitrile synthesis through catalyzed cascades involving acid-nitrile exchange
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Irreversible acid-nitrile exchange reactions using both glutaronitrile and (phenylsulfonyl)acetonitrile may be catalyzed by Lewis acids. Whereas a cyclization towards imides displaces the equilibria in the reaction with dinitriles, a decarboxylation step is involved when using the (phenylsulfonyl)acetonitrile. Georg Thieme Verlag Stuttgart New York.
- Cartigny, Damien,Dos Santos, Aurelie,El Kaim, Laurent,Grimaud, Laurence,Jacquot, Roland,Marion, Philippe
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p. 1802 - 1806
(2014/07/08)
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- Efficient catalytic hydrogenation of N-unsubstituted cyclic imides to cyclic amines
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The hydrogenation of N-unsubstituted cyclic imides to the corresponding cyclic amines has been performed selectively with heterogeneous catalysts obtained from rhodium and molybdenum carbonyl precursors. Various substrates were reduced in good to high yields and selectivities. Platinum-based catalysts also proved to be efficient. Furthermore, gram-scale experiments were performed and the catalysts could be recycled.
- Maj, Anna M.,Suisse, Isabelle,Pinault, Nathalie,Robert, Nicolas,Agbossou-Niedercorn, Francine
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p. 2621 - 2625
(2015/04/14)
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- AMIDOALKYLPIPERAZINYL DERIVATIVES FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISEASES
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The invention relates to novel amidoalkylpiperazinyl derivatives of tricyclic heterocyclic systems of general formula (I), wherein Z represents -NH- and X represents -S-, or Z represents -S- and X represents >C=C1 represents H or -CH3, R6 and R7 both represent H, n is an integer from 0 to 4 inclusive, G represents a cyclic amide or imide moiety, and optical isomers, geometric isomers, and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of the central nervous system disorders.
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Page/Page column 28
(2013/03/26)
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- METHOD FOR CONVERSION OF DIAMMONIM SUCCINATE IN FERMENTATION BROTH TO 2-PYRROLIDONE AND N-METHYLPYRROLIDONE
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This invention relates to a process for preparing 2-pyrroiidone (also called 2- pyrrolidinone) and N-methylpyrrolidone (also called N-methylpyrrolidinone) from diammonium succinate in fermentation broth. In the first stage of this invention, renewable carbon resources are utilized to produce diammonium succinate through biological fermentation. In the second stage of this present invention, diammonium succinate is converted into 2-pyrroiidone and N-methylpyrrolidone through a two step reaction. Both the steps of the reaction leading to the production of 2-pyrroiidone and N-methylpyrrolidone are carried out in a solvent phase to prevent the loss of succinimide through hydrolysis.
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Paragraph 094
(2013/03/28)
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- NBS-initiated electrophilic phenoxyetherification of olefins
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A one-pot electrophilic phenoxyetherification using an olefin, a cyclic ether, a phenol, and N-bromosuccinimide has been developed. This type of multicomponent reaction (MCR) is useful in the synthesis of building blocks that are potentially applicable to
- Ke, Zhihai,Yeung, Ying-Yeung
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supporting information
p. 1906 - 1909
(2013/06/04)
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- Molecular products from the thermal degradation of glutamic acid
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The thermal behavior of glutamic acid was investigated in N2 and 4% O2 in N2 under flow reactor conditions at a constant residence time of 0.2 s, within a total pyrolysis time of 3 min at 1 atm. The identification of the main pyrolysis products has been reported. Accordingly, the principal products for pyrolysis in order of decreasing abundance were succinimide, pyrrole, acetonitrile, and 2-pyrrolidone. For oxidative pyrolysis, the main products were succinimide, propiolactone, ethanol, and hydrogen cyanide. Whereas benzene, toluene, and a few low molecular weight hydrocarbons (propene, propane, 1-butene, and 2-butene) were detected during pyrolysis, no polycyclic aromatic hydrocarbons (PAHs) were detected. Oxidative pyrolysis yielded low molecular weight hydrocarbon products in trace amounts. The mechanistic channels describing the formation of the major product succinimide have been explored. The detection of succinimide (major product) and maleimide (minor product) from the thermal decomposition of glutamic acid has been reported for the first time in this study. Toxicological implications of some reaction products (HCN, acetonitrile, and acyrolnitrile), which are believed to form during heat treatment of food, tobacco burning, and drug processing, have been discussed in relation to the thermal degradation of glutamic acid.
- Kibet, Joshua K.,Khachatryan, Lavrent,Dellinger, Barry
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p. 7696 - 7704
(2013/09/02)
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- PROCESS FOR THE PREPARATION OF IMIDES AND DERIVATIVES THEREOF AND USES
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A process for the preparation of imides and also the uses thereof, especially as intermediates for the preparation of solvents, in particular of diester solvents, is described. Further described is a process for preparing cyclic imides and derivatives thereof, especially the corresponding carboxylic acids.
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Paragraph 0169-0172
(2014/01/08)
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- A novel ene-reductase from Synechococcus sp. PCC 7942 for the asymmetric reduction of alkenes
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The increasing demand for enantiopure molecules in the pharmaceutical and fine-chemical industry requires the availability of well-characterized and efficient biocatalysts for asymmetric syntheses. Thereby, asymmetric reduction of alkenes represents one of the most employed reactions for the production of chiral molecules. Here, we present a novel ene-reductase from the cyanobacterium Synechococcus sp. PCC 7942, a member of the old yellow enzyme family, capable of reducing CC bonds in a anti-specific fashion. We evaluated its biocatalytic potential by characterizing the substrate spectrum, cofactor preference, stereoselectivity and biochemical properties. This NADPH-dependent flavoprotein accepted a wide range of activated alkenes and displayed a pH optimum between pH 7.6 and pH 8.6. A C-terminal His6-tag decreased the enzyme activity 2.7-fold, but did not influence the stereoselectivity. The reduction of (R)-carvone and 2-methylmaleimide yielded (R)-products with high optical purities (98% de and >99% ee, respectively), pointing out the applicability of this new biocatalyst in the stereoselective production of chiral compounds.
- Fu, Yilei,Hoelsch, Kathrin,Weuster-Botz, Dirk
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p. 1988 - 1997
(2013/02/25)
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- Method for producing pyrrolidones from succinates from fermentation broths
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The present invention relates to a process for preparing a compound II or a composition comprising the compound II to a composition comprising succinimide and to a composition prepared by the process according to the invention.
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Page/Page column 18-19
(2011/10/03)
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- Triphenylene-Benzofuran/Benzothiophene/Benzoselenophene Compounds With Substituents Joining To Form Fused Rings
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Compounds comprising a triphenylene moiety and a benzo- or dibenzo-moiety are provided. In particular, the benzo- or dibenzo-moiety has a fused substituent. These compounds may be used in organic light emitting devices, particularly in combination with yellow, orange and red emitters, to provide devices with improved properties.
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- A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine
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A divergent and regioselective synthesis of either 3-substituted benzisoxazoles or 2-substituted benzoxazoles from readily accessible ortho-hydroxyaryl N-H ketimines is described. The reaction proceeds in two distinct pathways through a common N-Cl imine intermediate: (a) N-O bond formation to form benzisoxazole under anhydrous conditions and (b) NaOCl mediated Beckmann-type rearrangement to form benzoxazole, respectively. The reaction path also depends on the electronic nature of the aromatic ring, with the electron-rich aromatic rings favoring the rearrangement and the electron-deficient rings favoring the N-O bond formation. A Beckmann-type rearrangement mechanism via net [1,2]-aryl migration for the formation of 2-substituted benzoxazole is proposed.
- Chen, Cheng-Yi,Andreani, Teresa,Li, Hongmei
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supporting information; scheme or table
p. 6300 - 6303
(2012/01/05)
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- A mild and facile synthesis of cyclic imides using pyridinium chlorochromate
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A mild and facile synthetic method of cyclic imides is presented. These compounds are widely used in the synthesis of novel medical, polymeric, photonic and electronic materials. Compared with traditional syntheses, the method reported has several advantages including mild conditions, simplified work-up and low cost.
- Yang, Yanyan,Wang, Ge,Cao, Xiaohui,Yan, Xilong,Chen, Ligong
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p. 657 - 658,2
(2020/07/30)
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- METHOD FOR PREPARING ORTHO-SUBSTITUTED AMINOFERROCENES
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The present disclosure relates to a method for preparing an ortho-substituted aminoferrocene comprising reacting an aminoferrocene with a Lewis acid and a lithiating reagent in the presence of an electrophile to form the ortho-substituted aminoferrocene.
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Page/Page column 22
(2010/06/16)
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- ANALOGS OF INDOLE-3-CARBINOL AND THEIR USE AS AGENTS AGAINST INFECTION
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Compounds useful as antibacterial agents are provided. The compounds are analogs of indole-3-carbinol and have a backbone selected from dihydroindolo[2,3-b]carbazole, 2,2'-diindolylmethane, 2',3-diindolylmethane, and 3,3'-diindolylmethane. The compounds are useful therapeutic and prophylactic treatment of bacterial infections in mammals. Methods of synthesis of the compounds are provided, as are pharmaceutical compositions containing the compounds.
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Page/Page column 64
(2010/04/23)
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- Preparative and mechanistic studies toward the rational development of catalytic, enantioselective selenoetherification reactions
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A systematic investigation into the Lewis base catalyzed, asymmetric, intramolecular selenoetherification of olefins is described. A critical challenge for the development of this process was the identification and suppression of racemization pathways available to arylseleniranium ion intermediates. This report details a thorough study of the influences of the steric and electronic modulation of the arylselenenyl group on the configurational stability of enantioenriched seleniranium ions. These studies show that the 2-nitrophenyl group attached to the selenium atom significantly attenuates the racemization of seleniranium ions. A variety of achiral Lewis bases catalyze the intramolecular selenoetherification of alkenes using N-(2-nitrophenylselenenyl)succinimide as the electrophile along with a Bronsted acid. Preliminary mechanistic studies suggest the intermediacy of ionic Lewis base-selenium(II) adducts. Most importantly, a broad survey of chiral Lewis bases revealed that 1,1′-binaphthalene-2,2′-diamine (BINAM)-derived thiophosphoramides catalyze the cyclization of unsaturated alcohols in the presence of N-(2-nitrophenylselenenyl)succinimide and methanesulfonic acid. A variety of cyclic seleno ethers were produced in good chemical yields and in moderate to good enantioselectivities, which constitutes the first catalytic, enantioselective selenofunctionalization of unactivated olefins.
- Denmark, Scott E.,Kalyani, Dipannita,Collins, William R.
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supporting information; experimental part
p. 15752 - 15765
(2011/02/22)
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- Visible-light-promoted Wohl-Ziegler functionalization of organic molecules with N-bromosuccinimide under solvent-free reaction conditions
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The visible-light-induced transformation of toluenes with N-bromosuccinimide (NBS) under solvent-free reaction conditions (SFRC) was studied. The reaction took place in spite of the very restricted molecular motion; toluenes could be regioselectively converted to benzyl bromides. Selective radical-chain reactions with NBS were carried out in liquid/liquid and in solid/solid systems; furthermore, reactions could be performed in the presence of air. The radical scavenger TEMPO (=2,2,6,6-tetramethylpiperidin-1- yloxy) completely suppressed the side-chain bromination of toluenes with NBS under SFRC. Electron-withdrawing groups decreased the reactivity of the toluenes, and the Hammett reaction constant ρ+ = -1.7 indicated involvement of polar radical intermediates with electrophilic character.
- Jereb, Marjan,Zupan, Marko,Stavber, Stojan
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scheme or table
p. 555 - 566
(2009/09/06)
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- METHOD OF PRODUCING A CARBOXYLIC ALKYL ESTER
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The present invention relates to a novel process for preparing alkyl polycarboxylates from an aqueous solution of an ammonium salt of the polycarboxylic acid by reactive distillation, and to a process for hydrogenating the alkyl carboxylates prepared in this way.
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Page/Page column 7; 8-9
(2009/06/27)
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- The synthesis of unsubstituted cyclic imides using hydroxylamine under microwave irradiation
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Unsubstituted cyclic imides were synthesized from a series of cyclic anhydrides, hydroxylamine hydrochloride (NH2OH·HCl), and 4-N,N-dimethylamino-pyridine (DMAP, base catalyst) under microwave irradiation in monomode and multimode microwaves. This novel microwave synthesis produced high yields of the unsubstituted cyclic imides for both the monomode (61-81%) and multimode (84-97%) microwaves.
- Benjamin, Ellis,Hijji, Yousef
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p. 157 - 169
(2008/09/17)
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- Oligomers and Polymers
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An optionally substituted oligomer or polymer comprising a repeat unit of formula (I); wherein each Ar1 and Ar3 is the same or different and independently represents an optionally substituted aryl or heteroaryl; n is at least 1; Ar2 represents an optionally substituted aryl or heteroaryl comprising a linking ring to which the two nitrogen atoms are both directly linked; and at least one of Ar2 and either or both of Ar1 is substituted with at least one substituent.
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- Gold and gold-platinum as active and selective catalyst for biomass conversion: Synthesis of γ-butyrolactone and one-pot synthesis of pyrrolidone
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It has been found that gold is highly active and selective catalyst for the hydrogenation of succinic anhydride (SAN) to γ-butyrolactone (GBL). Using TiO2 as support and performing the reaction in presence of molecular sieves, it was possible to obtain the highest reaction rate ever obtained with 97% selectivity to GBL at 97% conversion. The process appears to be controlled by H2 dissociation on gold and the catalytic activity can be further improved, without loss of selectivity, by adding a very small amount of Pt (100 ppm) to increase the rate of H2 dissociation. We also found that gold is an efficient catalyst for the one-pot conversion of SAN into pyrrolidone and pyrrolidone derivates.
- Budroni, Gerolamo,Corma, Avelino
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experimental part
p. 403 - 408
(2009/02/05)
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