- Ceria nanoparticles as heterogeneous catalyst for CO2 fixation by ω-aminoalcohols
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In contrast to γ-Al2O3, TiO2, ZrO2, MgO and Y2O3, CeO2 is a reusable catalyst for the reaction of CO2 with ω-aminoalcohols to form cyclic carbamates; the highest yield (68%) was obtained for the preparation of N-alkyl 1,3-oxazolidin-2-ones from N-alkyl ethanolamines.
- Juarez, Raquel,Concepcion, Patricia,Corma, Avelino,Garcia, Hermenegildo
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Read Online
- Microwave assisted synthesis of fragrant jasmone heterocyclic analogues
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cis-Jasmone, from jasmonoid group, is an important jasmine odor fragrance compound. The syntheses of new heterocyclic analogues of jasmone were described. Five analogues of this compound were prepared under microwave irradiation and the results of the microwave assisted syntheses were compared with classical, thermally initiated reactions in solvent. Microwave reactions were carried out successfully, and reaction times were significantly reduced to a few minutes. Three of five obtained analogues, pyrrolidinone, oxazolidinone and thiazolidinone demonstrated an interesting, specific odor which was compared with floral, typical jasmine odor of jasmone.
- Pawelczyk, Anna,Zaprutko, Lucjusz
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Read Online
- Microwave assisted synthesis of unsaturated jasmone heterocyclic analogues as new fragrant substances
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Taking the rising interest in jasmone structure based fragrant compounds into account it has been decided to take up an attempt to synthesize the new heterocyclic derivatives of this 2,3-disubstituted cyclopentenone, which could be characterized by the ability of interaction with the same receptors with which jasmone affects. Obtained structures of unsaturated heterocyclic derivatives are based on pyrrolidinone, oxazolidinone, pyrazolidinone, pyrazolone and thiazolidinone systems with 2-double or 2-triple unsaturated five-carbon side chain. The rapid, highly yielding and ecofriendly microwave assisted organic syntheses (MAOS) have been used to obtain compounds mentioned above. Odor evaluation and relationships between their structure and osmic properties for all synthesized fragrant compounds have been studied. It has been shown that the majority of the obtained compounds have exhibited interesting, very intensive and fixative fragrant properties.
- Pawelczyk, Anna,Zaprutko, Lucjusz
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Read Online
- Effective scCO2-ionic liquid reaction system based on symmetric aliphatic ammonium salts for the rapid CO2 fixation with aziridine to 2-oxazolidinone
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The hybrid reaction system composed of supercritical carbon dioxide and room temperature ionic liquid based on symmetric tetraalkyl ammonium salts can effectively promote the carbon dioxide fixation from aziridine to 2-oxazolidinone in the presence of iod
- Kawanami, Hajime,Matsumoto, Hajime,Ikushima, Yutaka
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Read Online
- A sustainable protocol for the facile synthesis of zinc-glutamate MOF: An efficient catalyst for room temperature CO2 fixation reactions under wet conditions
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A water stable zinc-MOF (ZnGlu) catalyst was facilely prepared from the proteinogenic amino acid, l-glutamic acid at room temperature in aqueous medium. CO2 fixations were promoted by the ZnGlu catalyst's inherently coordinated water and externally added water in yielding cyclic carbonate and cyclic urethane at room temperature. This eliminates the need for catalyst activation, making ZnGlu a ready-to-use catalyst. The enhanced CO2 cycloaddition with added water hints at the application of ZnGlu in wet flue gas conversions. This is the first reported attempt for the use of an MOF in the cycloaddition of aziridine and CO2.
- Kathalikkattil, Amal Cherian,Roshan, Roshith,Tharun, Jose,Babu, Robin,Jeong, Gyeong-Seon,Kim, Dong-Woo,Cho, Sung June,Park, Dae-Won
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Read Online
- Room Temperature Cu-Catalyzed N-Arylation of Oxazolidinones and Amides with (Hetero)Aryl Iodides
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N,N′-Bis(pyridin-2-ylmethyl)oxalamide (BPMO) was found to be an apposite promoter for the Cu-catalyzed N-arylation of oxazolidinones and primary and secondary amides with (hetero)aryl iodides at room temperature. Excellent chemoselectivity reached between
- Bhunia, Subhajit,De, Subhadip,Ma, Dawei
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supporting information
p. 1253 - 1257
(2022/02/09)
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- SBA-15 Supported Dendritic ILs as a Green Catalysts for Synthesis of 2-Imidazolidinone from Ethylenediamine and Carbon Dioxide
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In this work, a simple and facile approach is conducted for preparing many new SBA-15 supported dendritic imidazolium ILs heterogeneous catalysts SBA-15/IL(1–3) having high ionic density from SBA-15. SBA-15/IL(3) as a green heterogeneous catalyst can be used for synthesis of 2-imidazolidinone from ethylenediamine and carbon dioxide and considering solvent-free condition. SBA-15/IL(3) showed to have the highest catalytic activity besides a positive dendritic influence on the yields of the synthesis of 2-imidazolidinone in the presence of CO2 is seen because of existing the high-density peripheral zwitterionic ionic liquid functional groups on the biobased SBA-15/IL(3) catalyst surfaces. Graphical Abstract: [Figure not available: see fulltext.]
- Min, Qingwang,Miao, Penghua,Liu, Jinghan,Ma, Jianjun,Qi, Meijuan,Shamsa, Farzaneh
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p. 1476 - 1487
(2021/07/26)
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- Ionic liquids/ZnO nanoparticles as recyclable catalyst for polycarbonate depolymerization
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A useful protocol for waste bis-phenol A-polycarbonates (BPA-PC) chemical recycling is proposed based on a bifunctional acid/basic catalyst composed by nanostructured zinc oxide and tetrabutylammonium chloride (ZnO-NPs/NBu4Cl) in quality of Lewis acid and base, respectively. Retro-polymerization reaction proved to be of general application for several nucleophiles, including water, alcohols, amines, polyols, aminols and polyamines, leading to the complete recovery of BPA monomer and enabling the PC polymer to function as a green carbonylating agent (green phosgene alternative) for preparing carbonates, urethanes and ureas. A complete depolymerization can be obtained in seven hours at 100 °C and ZnO nanocatalyst can be recycled several times without sensible loss of activity. Remarkably, when polycarbonate is reacted with glycerol, it is possible to realize in a single process the conversion of two industrial wastes (BPA-PC and glycerol) into two valuable chemicals like BPA monomer and glycerol carbonate (the latter being a useful industrial solvent and fuel additive).
- Iannone, Francesco,Casiello, Michele,Monopoli, Antonio,Cotugno, Pietro,Sportelli, Maria Chiara,Picca, Rosaria Anna,Cioffi, Nicola,Dell'Anna, Maria M.,Nacci, Angelo
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p. 107 - 116
(2016/12/09)
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- Catalytic Oxidative Carbonylation of Amino Moieties to Ureas, Oxamides, 2-Oxazolidinones, and Benzoxazolones
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The direct syntheses of ureas, oxamides, 2-oxazolidinones, and benzoxazolones by the oxidative carbonylation of amines, β-amino alcohols, and 2-aminophenols allows us to obtain high value added molecules, which have a large number of important applications in several fields, from very simple building blocks. We have found that it is possible to perform these transformations using the PdI2/KI catalytic system in an ionic liquid, such as 1-butyl-3-methylimidazolium tetrafluoroborate, as the solvent, the solvent/catalyst system can be recycled several times with only a slight loss of activity, and the product can be recovered easily by crystallization.
- Mancuso, Raffaella,Raut, Dnyaneshwar S.,Della Ca, Nicola,Fini, Francesco,Carfagna, Carla,Gabriele, Bartolo
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p. 2204 - 2211
(2015/07/15)
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- Copper(II)-catalysed oxidative carbonylation of aminols and amines in water: A direct access to oxazolidinones, ureas and carbamates
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Copper(II) chloride catalyses the oxidative carbonylation of aminols, amine and alcohols to give 2-oxazolidinones, ureas and carbamates. Reaction proceeds smoothly in water under homogeneous conditions (Ptot = 4 MPa; PO2 = 0.6 MPa, PCO), at 100°C in relatively short reaction times (4 h) and without using bases or any other additives. This methodology represents an economic and environmentally benign non-phosgene alternative for the preparation of these three important N-containing carbonyl compounds.
- Casiello, Michele,Iannone, Francesco,Cotugno, Pietro,Monopoli, Antonio,Cioffi, Nicola,Ciminale, Francesco,Trzeciak, Anna M.,Nacci, Angelo
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- Efficient synthesis of 2-oxazolidinones from epoxides and carbamates catalyzed by amine-functionalized ionic liquids
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A series of amine-functionalized ionic liquids were prepared and their catalytic performance was tested in the synthesis of 2-oxazolidinones from epoxides and carbamates. Under optimized reaction conditions, good to excellent yields of various 2-oxazolidinones were achieved with different epoxides and carbamates. Moreover, the amine-functionalized ionic liquid catalyst could be easily recovered and reused without significant loss in activity.
- Shang, Jianpeng,Li, Zuopeng,Su, Caina,Guo, Yong,Deng, Youquan
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p. 71765 - 71769
(2015/09/08)
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- Aluminium-Catalysed Oxazolidinone Synthesis and their Conversion into Functional Non-Symmetrical Ureas
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An efficient and practical aluminium-catalysed approach towards a range of functional oxazolidinones is reported. The method is based on cheap and readily available starting materials including terminal and internal (bicyclic) epoxides and phenyl carbamate. The oxazolidinones serve as highly useful synthons for the high yield preparation of non-symmetrical ureas by nucleophilic ring-opening affording the targeted urea compounds with excellent functional group diversity, high regioselectivity and isolated yields up to >99%.
- Laserna, Victor,Guo, Wusheng,Kleij, Arjan W.
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p. 2849 - 2854
(2015/09/28)
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- Synthesis of tricyclic nitrogen heterocycles by a sequence of palladium-catalyzed N-H and C(sp3)-H arylations
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A range of tricyclic nitrogen heterocycles were synthesized in a straightforward and efficient manner via a sequence involving palladium-catalyzed N-arylation and C(sp3)-H arylation as the key steps. Whereas the C(sp3)-H arylation furnished fused 6,5,6-membered ring systems efficiently, the formation of the more strained 6,5,5-membered systems proved to be more challenging and required a subtle adjustment of the reaction conditions.
- Guyonnet, Mathieu,Baudoin, Olivier
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supporting information; experimental part
p. 398 - 401
(2012/02/15)
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- Efficient synthesis of 2-oxazolidinone from epoxides and carbamates with binary MgFe oxides as a magnetic solid base catalyst
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Magnetic binary MgFe oxides were prepared by co-precipitation method, characterized and tested in the synthesis of 2-oxazolidinones from epoxides and carbamates. The catalytic results showed that the catalyst with Mg/Fe molar ratio of 1 and calcined at 400°C exhibited superior catalytic activity. The catalyst could be magnetically separated, recycled and reused for five runs without noticeable deactivation. Under the optimized conditions, various 2-oxazolidinones derivatives were successfully synthesized with good to excellent isolated yields.
- Shang, Jianpeng,Liu, Shimin,Lu, Liujin,Ma, Xiangyuan,He, Yude,Deng, Youquan
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- Efficient route for oxazolidinone synthesis using heterogeneous biopolymer catalysts from unactivated alkyl aziridine and CO2 under mild conditions
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Biopolymers made of polysaccharide chains are emerging as promising materials for designing efficient, cheap, environmental friendly and recyclable heterogeneous catalysts. In this study, we synthesized a series of covalently functionalized chitosan-alkyl pyridinium halides (CS-RPX, R = ethyl, propyl, butyl, hexyl and X = Cl, Br) and evaluated their potential application as catalysts for the chemical transformation of CO2 to 4-methyl-2-oxazolidinone using 2-methylaziridine under mild reaction conditions. The catalysts were characterized using different physicochemical methods, including X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS), thermo gravimetric analysis (TGA), elemental analysis (EA) and field emission scanning electron microscopy (FE-SEM). 1H NMR, GC-MS, EA and FT-IR were used to confirm successful oxazolidinone formation. Cycloaddition was found to proceed through the synergistic effect of the hydroxyl and amine groups of chitosan together with the anion. The catalyst was reused five times after the cycloaddition reaction, with a loss of 2-6% in conversion and 1-3% in selectivity per cycle. The effect of different reaction parameters, such as catalyst amount, time, temperature and CO2 pressure were studied to determine the reaction conditions that resulted in the highest conversion and selectivity.
- Kathalikkattil, Amal Cherian,Tharun, Jose,Roshan, Roshith,Soek, Han-Geul,Park, Dae-Won
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p. 107 - 114
(2013/02/25)
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- Synthesis of some 2-Oxazolidinones in mild conditions
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One step efficient protocol for the synthesis of 2-oxazolidinones in paste chemical medium is described under microwave activation with 80 % yield.
- Bratulescu, George
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experimental part
p. 929 - 930
(2011/12/15)
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- The solvent-free and catalyst-free conversion of an aziridine to an oxazolidinone using only carbon dioxide
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It has been found for the first time at room temperature that the reaction of an unactivated 2-alkyl or 2-aryl aziridine with carbon dioxide to generate the corresponding oxazolidinone does not need any form of catalysis or solvent to proceed in high yiel
- Phung, Chau,Ulrich, Rani M.,Ibrahim, Mostafa,Tighe, Nathaniel T. G.,Lieberman, Deborah L.,Pinhas, Allan R.
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experimental part
p. 3224 - 3229
(2011/12/16)
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- Synthesis of urea derivatives from amines and CO2 in the absence of catalyst and solvent
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Urea derivatives are obtained in mild to good yield from the reactions of primary aliphatic amines with CO2 in the absence of any catalysts, organic solvents or other additives. To optimize reaction conditions, experimental variables including temperature, pressure, the concentration of amine, reaction time etc. were studied. Satisfactory yields were obtained at the optimized conditions that are comparable to the presence of catalyst and solvent. The preliminary investigation of the reaction mechanism showed that alkyl ammonium alkyl carbamate was quickly formed as the intermediate, and then the final product was formed by the intramolecular dehydration.
- Wu, Chaoyong,Cheng, Haiyang,Liu, Ruixia,Wang, Qiang,Hao, Yufen,Yu, Yancun,Zhao, Fengyu
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experimental part
p. 1811 - 1816
(2011/02/22)
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- ALCOHOL PRODUCTION METHOD BY REDUCING ESTER OF LACTONE WITH HYDROGEN
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Provided is an alcohol production method comprising the step of reducing an ester or a lactone with hydrogen to produce a corresponding alcohol without addition of a base compound by using, as a catalyst, a ruthenium complex represented by the following general formula (1): [in-line-formulae]RuH(X)(L1)(L2)n ??(1)[/in-line-formulae] wherein X represents a monovalent anionic ligand,L1 represents a tetradentate ligand having at least one coordinating phosphino group and at least one coordinating amino group or a bidentate aminophosphine ligand having one coordinating phosphino group and one coordinating amino group, andL2 represents a bidentate aminophosphine ligand having one coordinating phosphino group and one coordinating amino group, provided thatn is 0 when L1 is the tetradentate ligand, and n is 1 when L1 is the bidentate aminophosphine ligand.
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Page/Page column 18
(2010/04/23)
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- Synthesis of 2-oxazolidinones by salen-Co-complexes catalyzed oxidative carbonylation of β-amino alcohols
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2-Oxazolidinones are synthesized in high yield by oxidative carbonylation of β-amino alcohols using salen-Co(II)/NaI or salen-Co(III)-I as a catalyst and using CO as the carbonyl source. Studies of functional group compatibility using a series of substituted salen-Co(II) or salen-Co(III)-I complexes demonstrate a broad tolerance of functionality during the carbonylation reaction.
- Liu, Jian-Ming,Peng, Xin-Gao,Liu, Jian-Hua,Zheng, Shu-Zhan,Sun, Wei,Xia, Chun-Gu
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p. 929 - 932
(2008/02/04)
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- Efficient synthesis of oxazolidin-2-one via (chitosan-Schiff base)cobalt(II)-catalyzed oxidative carbonylation of 2-aminoalkan-1-ols
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The (chitosan-Schiff base)cobalt(II) complex was found to be an efficient catalyst for the oxidative carbonylation (CO/O2) of 2-aminoalkan-1-ols 1 to give oxazolidin-2-ones 2, in the presence of NaI. The effects of promoters, temperature, solvents, and other reaction conditions were investigated in this study.
- Liu, Jianming,Sun, Wei,Zheng, Shuzhan,Xia, Chungu
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p. 1593 - 1598
(2008/02/09)
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- Pd(Phen)Cl2 stabilized by ionic liquid: an efficient and reusable catalyst for biphasic oxidative cyclocarbonylation of β-aminoalcohols and 2-aminophenol
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Biphasic oxidative cyclocarbonylation of β-aminoalcohols and 2-aminophenol to synthesize corresponding 2-oxazolidinones were investigated in the presence of ionic liquid stabilized Pd(phen)Cl2 complex. Catalytic comparison results showed that, 1-butyl-3-methyl-imidazolium iodide salts (BMImI) can serve simultaneously as a specific stabilizer to protect the transition metal complex against deactivation, a promoter to increase the catalytic performance and a reaction medium to recycle the catalyst with unprecedented TOF value.
- Li, Fuwei,Xia, Chungu
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p. 4845 - 4848
(2008/02/05)
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- A highly efficient sulfur-catalyzed oxidative carbonylation of primary amines and β-amino alcohols
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A highly efficient sulfur-catalyzed oxidative carbonylation of aliphatic amines and aliphatic β-amino alcohols to ureas and 2-oxazolidinones, respectively, was developed. Sodium nitrite was involved in the reoxidation of hydrogen sulfide to sulfur in the catalytic oxidative carbonylation cycle. Georg Thieme Verlag Stuttgart.
- Peng, Xingao,Li, Fuwei,Xia, Chungu
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p. 1161 - 1164
(2007/10/03)
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- Aliphatic poly(urethane-amine)s synthesized by copolymerization of aziridines and supercritical carbon dioxide
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A reaction of aziridines and carbon dioxide (CO2) proceeds under supercritical conditions to give random copolymers containing urethane and amine moieties. The ratio of urethane and amine linkages in the product can be controlled by reaction conditions including temperature and pressure as well as addition of N,N-dimethylacetamide as a cosolvent. An aqueous solution of the copolymer obtained from 2-methylaziridine and CO2 undergoes a thermally induced phase transition at a lower critical solution temperature (LCST). The critical temperature is highly sensitive to changes in the primary structure of the products. The use of supercritical CO2 (scCO 2) allows us to construct a functional material through the effective chemical fixation of CO2.
- Ihata, Osamu,Kayaki, Yoshihito,Ikariya, Takao
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p. 6429 - 6434
(2008/02/02)
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- FUNGICIDAL 4-(2-AMINOPYRIDIN-4-YL)-N-PHENYL-1,3,5-TRIAZIN-2-AMINE DERIVATIVES
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The present invention relates to triazine derivatives, especially 4-(2-aminopyridin-4-yl)-N-phenyl-1,3,5-triazin-2-amine derivatives and their use as fungicidal compositions. Novel compounds showing fungicidal activity are disclosed and further, novel compositions containing 4-(2-aminopyridin-4-yl)-N-phenyl-1,3,5- triazin-2-amine derivatives can be used in fungicide applications.
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Page/Page column 15-16
(2008/06/13)
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- Synthesis of 2-oxazolidinone catalyzed by palladium on charcoal: A novel and highly effective heterogeneous catalytic system for oxidative cyclocarbonylation of β-aminoalcohols and 2-aminophenol
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Oxidative cyclocarbonylation of β-aminoalcohols and 2-aminophenol to synthesize corresponding 2-oxazolidinones catalyzed by a Pd/C-I2 heterogeneous catalytic system has been developed which gave excellent selectivity and high turnover frequency (TOF) values 15 times larger than the best results previously reported. The catalyst could be reused for five times almost without losing its catalytic activity and selectivity. The effects of promoters, pretreatment, solvents, and reaction conditions have been investigated.
- Li, Fuwei,Xia, Chungu
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p. 542 - 546
(2007/10/03)
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- ORGANIC COMPOUNDS
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Tertiary non-vinylic carbamates of molecular weight less than 350 are useful as fragrance ingredients. A method of preparation is also described.
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- Highly efficient chemical fixations of carbon dioxide and carbon disulfide by cycloaddition to aziridine under atmospheric pressure
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Cycloaddition of aziridine with carbon dioxide was successfully catalyzed by alkali metal halide or tetraalkylammonium halide to give the corresponding 5-membered cyclic urethane, 1,3-oxazolidin-2-one, selectively. The reaction can be performed at ambient
- Sudo, Atsushi,Morioka, Yosuke,Koizumi, Eri,Sanda, Fumio,Endo, Takeshi
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p. 7889 - 7891
(2007/10/03)
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- An improved procedure for the palladium-catalyzed oxidative carbonylation of β-amino alcohols to oxazolidin-2-ones
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A highly efficient oxidative cyclocarbonylation of β-amino alcohols and 2-aminophenol to oxazolidin-2-ones has been achieved by using PdI2 in conjunction with KI as the catalytic system in DME under relatively mild conditions (100 °C and 20 atm of a 4:1 mixture of CO and air).
- Gabriele, Bartolo,Mancuso, Raffaella,Salerno, Giuseppe,Costa, Mirco
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p. 601 - 604
(2007/10/03)
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- Regioselectivity and selective enhancement of carbon dioxide fixation of 2-substituted aziridines to 2-oxazolidinones under supercritical conditions
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Under supercritical CO2 conditions, regioselectivity in the carbon dioxide fixation of 2-substituted aziridines to 2-oxazolidinones was observed with good yields around 75%. Furthermore, when propylene imine was used in the place of aziridine,
- Kawanami, Hajime,Ikushima, Yutaka
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p. 3841 - 3844
(2007/10/03)
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- Synthesis of 2-oxazolidinones by direct palladium-catalyzed oxidative carbonylation of 2-amino-1-alkanols
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(equation presented) 2-Oxazolidinones 2 are obtained in excellent yields (up to 100%) and with unprecedented catalytic efficiencies (up to 2000 mol of product/mol of catalyst used) by direct Pdl2/Kl-catalyzed oxidative carbonylation of the readily available 2-amino-1-alkanols 1. Reactions are carried out in MeOH as the solvent at 100 °C using a 1/6/5 CO/O2/air mixture (60 atm total pressure at 25 °C).
- Gabriele, Bartolo,Salerno, Giuseppe,Brindisi, Donatella,Costa, Mirco,Paolo Chiusoli, Gian
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p. 625 - 626
(2007/10/03)
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- DERIVATIVES OF HETEROCYCLIC α-IMINOCARBOXYLIC ACIDS. 4. REDUCTION OF N-ALKOXYCARBONYL DERIVATIVES OF α-IMINOCARBOXYLIC ACIDS.
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When N-methoxycarbonyl and N-benzoxycarbonyl derivatives of methyl esters of aziridine-2-carboxylic acid, L-proline, L-thioproline, and pipecolic acid interact with NaBH4 in tert-butanol/methanol, the products of reduction of the C-methoxycarbonyl group o
- Nurdinov, R.,Liepin'sh, E. E.,Kalvin'sh, I. Ya.
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p. 1352 - 1357
(2007/10/02)
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- Substituted benzo[b]pyrans, processes for their preparation, their use and pharmaceutical preparations based on these compounds
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Benzo[b]pyran derivatives of the formula I STR1 with E--D equal to CH--CHOH or C=CH; X equal to oxygen or sulfur; Y equal to oxygen, sulfur, SO, SO2 or NR9 ; R1 equal to CN, NO2, Hal, alkoxycarbonyl, SO1-2
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- Practical Preparation of Chiral 4-Substituted 2-Oxazolidinones
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A versatile and practical route to both enantiomers of a wide variety of 4-substituted 2-oxazolidinones from the parent heterocycle is provided by regioselective substitutions via 4-methoxy derivative followed by chromatographic separation of the diastereomers derived from N-2-exo-methoxy-1-apocamphanecarbonylation.
- Ishizuka, Tadao,Kimura, Koreichi,Ishibuchi, Seigo,Kunieda, Takehisa
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p. 991 - 994
(2007/10/02)
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- Lipophilic analogues of sparsomycin as strong inhibitors of protein synthesis and tumor growth: A structure-activity relationship study
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Fourteen derivatives of sparsomycin (1) were synthesized. Six of them were prepared following a novel synthetic route starting from the L-amino acid alanine. Some physicochemical properties, viz. lipophilicity and water solubility, of selected derivatives were measured. The biological activity was tested in vitro in cell-free protein synthesis inhibition assays, in bacterial and tumor cell growth inhibition assays, and in the L1210 leukemia in vivo model in mice. Also for selected drugs the acute toxicity in mice was determined. Ribosomes from both an eukaryotic and a prokaryotic organism were used in the protein synthesis inhibition systems. A linear correlation between the lipophilicity parameters measured was observed. Water solubility and drug toxicity in mice were found to be linearly correlated with lipophilicity. All the derivatives studied are more lipophilic than 1. The deshydroxysparsomycin analogues (30-33) showed an interesting phenomenon: increase in hydrophobicity was accompanied by a considerable increase in water solubility. We found that an increase in hydrophobicity of the drug as a result of replacing the SMe group of 1 with larger alkylthio groups causes an increase in the biological activity of the drug. However, not only the hydrophobicity but also shape and size of the substituent are important; in the homologous series 1-9-10-11-12, 21-22-23-24, and 30-31-32-33, highest protein synthesis inhibitory and in vitro cytostatic activity is found with compounds 11, 23, and 32, respectively, and in comparison with the highly active n-butyl compound 10, the isomeric tert-butyl compound 13 is rather inactive. Polar substituents replacing the SMe group, i.e. Cl in 17 and 35, also render the molecule inactive. Substituting the bivalent sulfur atom for a methylene group decreases the drug's activity. This effect can be compensated for by increasing the length of the alkylsulfinyl side chain. The agreement between the results derived from cell-free and 'in vivo' tests is good. The assays using ribosomes of bacterial and eukaryotic organisms give similar results although the latter seem to be more sensitive to changes in hydrophobicity of the drug. Our results confirm the presence of a hydrophobic region at the peptidyl transferase center of the ribosome; the interaction of sparsomycin with this region is more pronounced in the eukaryotic particles. The sparsomycin analogues 11, 23, and 30 show the highest antitumor activity against L1210 leukemia in mice, their median T/C values are 386, 330, and 216%, respectively. Sparsomycin (1), showing a T/C value of 117%, is only marginally active against this tumor. The analogues tested are 5-100 times less toxic than 1.
- Van den Broek,Lazaro,Zylicz,Fennis,Missler,Lelieveld,Garzotto,Wagener,Ballesta,Ottenheijm
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p. 2002 - 2015
(2007/10/02)
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- Process for preparing 2-oxazolidone and its derivatives
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Process for preparing 2-oxazolidone and its derivatives by reacting react carbon dioxide with aziridine compound, preferably, in the presence of Lewis acid as a catalyst.
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