- PREPARATION OF CYCLIC CARBONATES AND 2-OXAZOLIDONES USING DI-2-PYRIDYL CARBONATE
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Cyclic carbonates and 2-oxazolidones are conveniently prepared in high yields by the reaction of diols and β-amino alcohols with di-2-pyridyl carbonate.It is of synthetic significance that the formation of cyclic carbonates in refluxing toluene occurs under essentially neutral conditions.
- Kim, Sunggak,Ko, Young Kwan
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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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- Synthesis of 2-oxazolidinones from CO2 and 1,2-aminoalcohols catalyzed by n-Bu2SnO
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The dehydrative condensation of 1,2-aminoalcohols with CO2 is found to proceed in NMP as solvent; 2-oxazolidinones are obtained in the yields of 53-94% when a commercially available tin compound, n-Bu2SnO is used as catalyst.
- Tominaga, Ken-Ichi,Sasaki, Yoshiyuki
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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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- Novel α-aminophosphonic acids. Design, characterization, and biological activity
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Novel α-aminophosphonic acids are synthesized reacting 1,3-oxazolidin-2-one derivatives with formaldehyde and phosphorus trichloride. Treatment of N-(phosphonomethyl)oxazolidinones with aqueous NaOH gave the expected α-aminophosphonic acids. The oxidation
- Naydenova, Emilia,Topashka-Ancheva, Margarita,Todorov, Petar,Yordanova,Troev, Kolio
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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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- 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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- Converting urea into high value-added 2-oxazolidinones under solvent-free conditions
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Zn-modified mesoporous Mg-Al nanoplates oxides were prepared by co-precipitation and further characterized and used in the synthesis of 2-oxazolidinones from urea and epoxides under solvent-free conditions. The characterization results suggested that Zn1.1Mg2.0AlO4.6, which featured more accessible active medium basic sites, were favorable for obtaining superior catalytic activity. This synthetic process is mild, convenient, simple and gives good yields up to 80%.
- Wang, Peixue,Li, Qinghe,Liu, Shimin,Deng, Youquan
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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.]
- Liu, Jinghan,Ma, Jianjun,Miao, Penghua,Min, Qingwang,Qi, Meijuan,Shamsa, Farzaneh
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- Synthesis of 2-oxazolidones by sulfur-assisted thiocarboxylation with carbon monoxide and oxidative cyclization with molecular oxygen under mild conditions
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Simple synthetic method on 2-oxazolidone derivatives was established. 2-Aminoethanols were easily subjected to the thiocarboxylation with carbon monoxide promoted by elemental sulfur, followed by the oxidative cyclization with molecular oxygen to give corresponding 2-oxazolidones in good yields under mild conditions (1 atm, rt). Furthermore, 2-imidazolidones and 2-thiazolidone were also prepared in good yields similarly.
- Mizuno, Takumi,Takahashi, Junko,Ogawa, Akiya
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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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- A novel way to chiral 2-oxazolidinones: selenium-catalyzed cyclocarbonylation of 2-aminoethanols
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Selenium-catalyzed cyclocarbonylation of 2-aminoethanols with CO under atmospheric pressure at 30 °C afforded 2-oxazolidinones in excellent yields without any other co-catalyst. The method was then applied to the syntheses of chiral 2-oxazolidinones and no racemization was detected.
- Li, Peng,Yuan, Xiaohua,Wang, Shudong,Lu, Shiwei
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- Synthesis of cyclic N-nitrourethanes by the simultaneous oxidative desulfurization and nitration of cyclic thiourethanes
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The reaction of five- and six-membered cyclic thiourethanes with acetyl nitrate results in a vigorous reaction that generates copious amounts of red-brown nitrogen oxide fumes and produces the corresponding cyclic N-nitrourethanes in high yields (>95%). The overall yield of the cyclic N-nitrourethanes starting from an aminoalcohol using the " thiourethane" route is superior to the conventional route going through the cyclic urethane. Copyright
- Willer, Rodney L.,Campbell, Christopher G.,Storey, Robson F.
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- Microwave-assisted preparation of cyclic ureas from diamines in the presence of ZnO
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A MW-assisted direct synthesis of cyclic ureas has been developed that proceeds expeditiously in the presence of ZnO thus shortening its reaction time; the process also eliminates the formation of byproducts when compared to the traditional methods involving conventional heating. A microwave-assisted facile method for the preparation of various ureas, cyclic ureas, and urethanes has been developed that affords nearly quantitative yield of products at 120°C (150 W), 71 kPa within 10 min using ZnO as a catalyst. The enhanced selectivity in this reaction is attributed to the deployment of ZnO whose absence results in poor yield and the generation of byproducts.
- Kim, Yong Jin,Varma, Rajender S.
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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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- 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-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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- Highly efficient synthesis of ureas and carbamates from amides by iodosylbenzene-induced hofmann rearrangement
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A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. Symmetric and asymmetric ureas and carbamates can be prepared by this procedure in up to 98 % yield. Ureidopeptides can also be prepared in good yield by this method. A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. By using this method, heterocyclic products can be easily obtained in excellent yield. Ureidopeptides can also be prepared in good yield by this procedure. Copyright
- Liu, Peng,Wang, Zhiming,Hu, Xianming
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experimental part
p. 1994 - 2000
(2012/05/05)
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- NOVEL AMIDE DERIVATIVE AND USE THEREOF AS MEDICINE
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Provided are a novel low-molecular-weight compound that suppresses production of induction type MMPs, particularly MMP-9, rather than production of hemostatic type MMP-2, as well as a prophylactic/therapeutic drug for autoimmune diseases or osteoarthritis
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Page/Page column 30; 31
(2011/10/04)
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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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- 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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- Synthesis of ring-fused oxazolo- and pyrazoloisoquinolinones by a one-pot Pd-catalyzed carboxamidation and aldol-type condensation cascade process
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(Chemical Equation Presented) A three-component cascade process is described for the synthesis of ring-fused oxazolo- and pyrazoloisoquinolinones by a one-pot carboxamidation/aldol-type condensation reaction. The cascade process involves Pd-catalyzed carboxamidation of an aryl halide/active methylene compound with oxazolidinone or pyrazolidinone, and subsequent intramolecular base-catalyzed cyclization/dehydration through an aldol-type condensation process, to give ring-fused oxazolo- and pyrazoloisoquinolinones. This methodology provides an easy one-step approach to these important classesof nitrogen-containing heterocycles and can tolerate a wide array of functional groups, including ester, nitrile, methoxy, and halide.
- Chouhan, Gagan,Alper, Howard
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supporting information; experimental part
p. 6181 - 6189
(2009/12/24)
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- Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines
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(Chemical Equation Presented) N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50°C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.
- May, Aaron E.,Willoughby, Patrick H.,Hoye, Thomas R.
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p. 3292 - 3294
(2008/09/20)
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- Facile one-pot synthesis of oxazolidin-2-ones from phenyl 2-hydroxyalkyl selenides
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A novel, convenient, efficient, three-step, one-pot synthesis of 2-oxazolidinones from phenyl 2-hydroxyalkyl selenides was developed. Using this methodology, 2-oxazolidinones are obtained in good yields (76-85%) by reaction of phenyl 2-hydroxyalkyl seleni
- Sheng, Shou-Ri,Luo, Hai-Rong,Huang, Zhen-Zhong,Sun, Wu-Kang,Liu, Xiao-Ling
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p. 2693 - 2699
(2008/02/12)
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- A facile one-pot solid-phase synthesis of oxazolidin-2-ones using polymer-supported 2-hydroxyalkyl selenide reagent
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A simple, efficient and environmentally friendly procedure for one-pot solid-phase synthesis of 2-oxazolidinones in moderate to good yields by reaction of polystyrene-supported 2-hydroxyalkyl selenide with benzoyl isocyanate and subsequent oxidation/cycli
- Hu, Qiao-Sheng,Sheng, Shou-Ri,Lin, Shu-Ying,Wei, Mei-Hong,Xin, Qin,Liu, Xiao-Ling
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- A novel and efficient (NHC)CuI (NHC = N-heterocyclic carbene) catalyst for the oxidative carbonylation of amino compounds
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Oxidative carbonylation of amino compounds to prepare corresponding 2-oxazolidinones, ureas, and carbamates selectively in the presence of (NHC)CuI without any additives was firstly achieved in good yields and selectivities.
- Zheng, Shuzhan,Li, Fuwei,Liu, Jianming,Xia, Chungu
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p. 5883 - 5886
(2008/02/09)
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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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- Modified Mg: Al hydrotalcite in the synthesis of oxazolidin-2-ones
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The modified Mg: Al (3: 1) hydrotalcite has been found to be an efficient catalyst in the conversion of carbamates into oxazolidin-2-ones under mild reaction conditions. A wide variety of oxazolidin-2-ones were obtained with excellent chemical yield. The Royal Society of Chemistry 2005.
- Cwik, Agnieszka,Fuchs, Aliz,Hell, Zoltan,Boejtoes, Ildiko,Halmai, Dora,Bombicz, Petra
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p. 967 - 969
(2007/10/03)
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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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- 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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- Hypervalent iodine oxidative rearrangement of anthranilamides, salicylamides and some β-substituted amides: A new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds
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Oxidation of anthranilamides, salicylamides and some β-substituted amides with iodobenzene diacetate in methanolic potassium hydroxide led to a new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds, respectively. The reaction probably occurs via initial Hofmann-type rearrangement followed by intramolecular cyclization of intermediate isocyanate.
- Prakash,Batra,Kaur,Sharma,Sharma,Singh,Moriarty
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p. 541 - 543
(2007/10/03)
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- Reactions of Relevance to the Chemistry of Aminoglycoside Antibiotics. Part 12. A Study of Cyclic Iminocarbonates
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A novel method for the replacement of a carbohydrate hydroxy-group by an amino-function via rearrangement of cyclic iminocarbonates has been developed.Several examples from the carbohydrate field illustrate that the overall process is strongly influenced
- Barton, Derek H. R.,Motherwell, William B.
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p. 1124 - 1131
(2007/10/02)
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