- MACROMOLECULAR COMPOSITIONS FOR BINDING SMALL MOLECULES
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The present invention relates to a method for preparing a macromolecular composition comprising phenylglyoxaldehyde-derivatives. The invention also relates to the macromolecular compositions per se, and to methods of using the macromolecular compositions. The macromolecular compositions are useful for undergoing subsequent reactions with small molecules, for instance to remove such small molecules from a solution.
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Page/Page column 7; 30-31; 34-35
(2021/05/29)
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- Method for continuously and quickly preparing DL-phenylglycine and analogue thereof
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The invention provides a method for continuously and quickly preparing DL-phenylglycine and an analogue thereof. The method comprises the steps of adding 2-hydroxyl-phenylacetonitrile and an analoguethereof (cyanohydrin for short) and an aqueous ammonium bicarbonate solution into a microchannel reactor for a reaction, controlling the reaction temperature to be 80-130 DEG C, and controlling the reaction pressure to be 0.5-2.0 MPa, wherein the standing time of the reactants in a microchannel is 1-8 min, and an aqueous solution of 5-phenyl-hydantoin and an analogue thereof (hydantoin for short)is obtained; adding the hydantoin and alkali into the microchannel reactor for a reaction, controlling the reaction temperature to be 120-200 DEG C, and controlling the reaction pressure to be 1.0-3.5MPa, wherein the standing time of the reactants in the microchannel is 1-8 min, and then a saline solution of phenylglycine and an analogue thereof is obtained; conducting acidification neutralization and crystallization to obtain the phenylglycine and the analogue thereof. According to the method, the microchannel reactor is adopted, the reaction time is greatly shorted, the reaction speed is increased, pyrolysis and polymerization of the cyanohydrin are reduced, no by-products are generated, the products are high in yield, clean and environmentally friendly, and the production cost is lowered.
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Paragraph 0025; 0028
(2019/07/04)
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- Facile One-Pot Synthesis of Substituted Hydantoins from Carbamates
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A novel and simple approach for the preparation of 3-substituted, 5-substituted, or 3,5-disubstituted hydantoins is reported. It involves the reaction of α-amino methyl ester hydrochlorides with carbamates to yield the corresponding ureido derivatives, which subsequently cyclize under basic conditions to produce substituted hydantoins in good yields. By applying this method, the bioactive anticonvulsant drug ethotoin was synthesized in good yield. The process avoids conventional multistep protocols and does not use the hazardous, irritant, toxic, or moisture-sensitive reagents, such as isocyanates or chloroformates, that are commonly used for the synthesis of these important compounds.
- Tanwar, Dinesh Kumar,Ratan, Anjali,Gill, Manjinder Singh
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supporting information
p. 2285 - 2290
(2017/10/06)
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- HAT INHIBITORS AND METHODS FOR THEIR USE
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Compounds having a structure of Formula I or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, wherein R1, R2a, R2b, R3a, R3b, R3c, R4a, R4b, R5, R6, Z and X are as defined herein are provided. Pharmaceutical compositions comprising such compounds and methods for treating various HAT-related conditions or diseases, including cancer, by administration of such compounds are also provided.
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Page/Page column 78; 79
(2016/04/10)
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- A Sustainable, Semi-Continuous Flow Synthesis of Hydantoins
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Hydantoins are an important class of heterocycles with applications in pharmacy, agriculture, and as intermediates in organic synthesis. Traditional synthetic procedures to access hydantoins are target oriented with multiple synthetic steps and often use reagents that are not commercially available or sustainable. Herein, an efficient process is described for accessing hydantoins starting from commercially available amines using consecutive gas–liquid transformations (oxygen, carbon dioxide). This semi-continuous process produced ten benzylic/aliphatic hydantoins in good overall yields (52–84 %).
- Vukeli?, Stella,Koksch, Beate,Seeberger, Peter H.,Gilmore, Kerry
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p. 13451 - 13454
(2016/09/13)
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- Continuous Synthesis of Hydantoins: Intensifying the Bucherer-Bergs Reaction
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A continuous Bucherer-Bergs hydantoin synthesis utilizing intensified conditions is reported. The methodology is characterized by a two-feed flow approach to independently feed the organic substrate and the aqueous reagent solution. The increased interfacial area of the biphasic reaction mixture and the lack of headspace enabled almost quantitative conversions within ca. 30 minutes at 120 °C and 20 bar even for unpolar starting materials. In addition, a selective N(3)-monoalkylation of the resulting heterocycles under batch microwave conditions is reported yielding potential acetylcholinesterase inhibitors.
- Monteiro, Julia L.,Pieber, Bartholom?us,Corrêa, Arlene G.,Kappe, C. Oliver
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supporting information
p. 83 - 87
(2015/12/26)
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- A one-pot synthesis of 5,5-disubstituted hydantoin derivatives using magnetic Fe3O4 nanoparticles as a reusable heterogeneous catalyst
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A facile and rapid method for the one-pot synthesis of 5,5-disubstituted hydantoins in the presence of magnetic Fe3O4 nanoparticles has been developed. The multicomponent reactions of carbonyl compounds (aldehydes and ketones), potassium cyanide and ammonium carbonate were carried out under solvent-free conditions to obtain various hydantoin derivatives. The magnetic catalyst could be readily separated by an external magnet from the reaction mixture. This procedure has many advantages, such as the use of a reusable magnetic catalyst, high yields, short reaction times, simplicity and very easiness with implementing the methodology.
- Safari, Javad,Javadian, Leila
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p. 1165 - 1171
(2013/12/04)
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- Microwave-promoted facile and rapid synthesis procedure for the efficient synthesis of 5,5-disubstituted hydantoins
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A fast, general, environmentally friendly, and facile method for preparation of 5, 5-disubstituted hydantoins from the reaction between ketone (or aldehyde) derivatives with KCN and ammonium carbonate under microwave irradiation is presented. The microwaves remarkably accelerated this reaction, the reaction times decreased dramatically, the reaction conditions were milder, and the yields were also greater. Also a comparative study of microwave versus classical conditions has been done. All the products were characterized by infrared, NMR, and CHN analysis, and their melting points are identical to those of the known compounds reported in the literature. This method might be useful in the future for the preparation of similar derivatives. Taylor & Francis Group, LLC.
- Safari, Javad,Gandomi-Ravandi, Soheila,Javadian, Leila
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supporting information
p. 3115 - 3120
(2014/01/06)
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- Ruthenium catalyzed hydroaminoalkylation of isoprene via transfer hydrogenation: Byproduct-free prenylation of hydantoins
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The ruthenium catalyst derived from Ru3(CO)12 and triphos [Ph2P(CH2CH2PPh2) 2] promotes the direct C-C coupling of isoprene with aryl substituted hydantoins 1a-1f at the diene C4-position to furnish products of n-prenylation 2a-2f. A mechanism involving hydantoin dehydrogenation followed by diene-imine oxidative coupling to furnish a transient aza-ruthencyclopentene is proposed.
- Schmitt, Daniel C.,Lee, Jungyong,Dechert-Schmitt, Anne-Marie R.,Yamaguchi, Eiji,Krische, Michael J.
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supporting information
p. 6096 - 6098
(2013/07/11)
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- Facile one-pot synthesis of 5-substituted hydantoins
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5-Substituted and 5,5-disubstituted hydantoins are synthesised from the corresponding aldehydes or ketones, using a one-pot, gallium(iii) triflate-catalysed procedure that is compatible with a range of substrates and solvents.
- Murray, Ross G.,Whitehead, David M.,Le Strat, Franck,Conway, Stuart J.
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supporting information; scheme or table
p. 988 - 991
(2009/02/05)
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- A Cu(I)-catalyzed C-H α-amination of esters. Direct synthesis of hydantoins
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This paper describes a novel intermolecular α-amination process of esters using CuCl as catalyst and di-tert-butyldiaziridinone as nitrogen source. A variety of hydantoins can be formed effectively under mild reaction conditions. Copyright
- Zhao, Baoguo,Du, Haifeng,Shi, Yian
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p. 7220 - 7221
(2008/12/20)
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- [(11)C] Carbon monoxide in selenium-mediated synthesis of (11)C-carbamoyl compounds.
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Using either amines, amino alcohols, or alcohols in selenium-mediated synthesis with [(11)C]carbon monoxide, 3 ureas, 6 carbamates, and 1 carbonate were labeled. Tetrabutylammonium fluoride ((TBA)F) was discovered to form a soluble and reactive complex with selenium and drastically increase the radiochemical yields. Of the selected carbamoyl compounds, one was a receptor ligand, one was an enzyme inhibitor, and one was a muscular relaxant pharmaceutical. The (11)C-target compounds were obtained in radiochemical yields ranging from low to almost quantitative and with specific radioactivity up to 1300 GBq/micromol. The radiochemical purity of the final products exceeded 98%. In one case, the corresponding (13)C-substituted compound was produced to verify the position of the (11)C-label. In a typical experiment starting with 16.4 GBq [(11)C]carbon monoxide, 7.0 GBq of LC-purified 5-phenyl-1,3-oxazolidin-[2-(11)C]-2-one was obtained within 20 min from start of the carbonylation reaction (84% decay-corrected radiochemical yield). The presented approach is an interesting alternative to the use of [(11)C]phosgene in labeling chemistry.
- Kihlberg, Tor,Karimi, Farhad,Langstroem, Bengt
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p. 3687 - 3692
(2007/10/03)
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- Process for the preparation of imidazolidine-2, 4-diones
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A process for the preparation of compounds of the general formula (I) by reacting an aldehyde compound of the general formula (II) with a urea compound of the general formula (III) in the presence of carbon monoxide and a catalytically active metal compound. Compounds of the general formula (I) are important intermediates for the synthesis of α-amino acids.
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- Palladium-catalyzed synthesis of substituted hydantoins - A new carbonylation reaction for the synthesis of amino acid derivatives
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One-step synthesis of substituted hydantoins can be achieved by the palladium-catalyzed 'ureidocarbonylation' of aldehydes with urea derivatives and carbon monoxide [Eq. (1)]. This surprisingly selective protocol converts substituted ureas into 1,5- and 1,3,5-substituted hydantoins in yields of up to 93 %.
- Beller, Matthias,Eckert, Markus,Moradi, Wahed A.,Neumann, Helfried
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p. 1454 - 1457
(2007/10/03)
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- Ultrasound-promoted synthesis of 5-substituted and 5,5-disubsntuted hydantoins
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Sonication of a mixture of industrial grade sodium cyanide (aqueous solution) and ammonium carbonate in aqueous alcohol with aldehydes or ketones affords the 5-substituted or 5,5-disubstituted hydantoins in 30-92percent yield.
- Li, Jital,Li, Lijun,Li, Tongshuang,Waog, Jianzhong
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p. 298 - 300
(2007/10/03)
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- Production of ring-substituted D-phenylglycines by microbial or enzymatic hydrolysis/deracemisation of the corresponding DL-hydantoins
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A series of 17 ring-mono and -disubstituted D-phenylglycine derivatives was prepared in high enantiomeric purity by enzymatic hydrolysis and deracemisation of the corresponding DL-hydantoins, using D-hydantoinase activities of microorganisms or purified enzymes, followed by diazotation of the resulting N-carbamyl-D-amino acids. No significant L-hydantoinase activity was found to produce the corresponding L-enantiomers.
- Garcia, Maria J.,Azerad, Robert
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- Preparation of 2,4-imidazolidinediones (hydantoins) from α-keto hemithioacetal and ureas
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5-Phenyl-2,4-imidazolidinedione (3a) and 1-aryl-5-phenyl-2,4-imidazolidinediones (3b-d) have been synthesized from α-keto hemithioacetal and urea or arylureas.
- Zou, Jian Ping,Lu, Zhong E.,Qiu, Li Hua,Chen, Ke Qian
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- Process for the preparation of arylhydantoins
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Process for the preparation of 5-arylhydantoins by reaction of an allantoin acid alkyl ester with an aryl compound in a concentrated inorganic acid at temperatures from room temperature to 150° C., with or without a phase transfer agent.
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- Synthesis of 5-benzoyl-5-phenyl- and 5-phenylhydroxymethyl-5phenylhydantoins as potential anticonvulsants
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A series of 5-benzoyl-5-phenyl- and 5-phenyl-5-phenylhydroxymethylhydantoins have been synthesized from the reaction of urea, N-monosubstituted ureas and sym-N,N-disubstituted ureas with phenyltriketone hydrate, via a pinacol-pinacolone-type rearrangement mechanism. The compounds were evaluated for anti-convulsant activity in mice.
- Crooks,Deeks,DeSimone
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p. 1113 - 1117
(2007/10/02)
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- Preparation of α-aminothioamides from aldehydes
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The conversion of aldehydes into α-aminonitriles and thence into imidazolidin-4-thiones has been studied.Hydrolysis of the appropriate imidazolidin-4-thiones gave thioamides of nine naturally occuring α-amino acids.The possible pre-biotic significance of these compounds is discussed.
- Paventi, Martino,Edward, John T.
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p. 282 - 289
(2007/10/02)
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- KINETICS AND MECHANISM OF BASE-CATALYZED CYCLIZATION OF SUBSTITUTED AMIDES AND NITRILES OF HYDANTOIC ACID
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Rates of base-catalyzed cyclizations of 8 substituted derivatives of hydantoic acid amide type R3-NH(5)-CO(4)-NR2(3)-CH2(2)-CO(1)-NHR1 and 9 nitriles type R3-NH(5)-CO(4)-NR2(3)-CHR1(2)-CN have been measured in aqueous and methanolic media.The cyclization of the amides in aqueous medium is also accompanied by hydrolysis of the hydantoins formed.In some cases the hydrolysis rate constant is greater than the corresponding cyclization reaction rate constant.With the least reactive amides, the cyclization is also accompanied by hydrolysis of the amide group.The ra te of the cyclization reactions in water is higher than that in methanol (at the same concentration of the lyate ions) by the factor of 10 - 100.Substitution of hydrogen at 3 and 5 positions by methyl or phenyl groups causes an acceleration of the cyclization reaction, whereas a substitution in the amide group causes a considerable retardation.The greatest acceleration of the cyclization (by as much as 4 orders) is caused by introduction of phenyl group to the N(5) position, which is due to a substantial increase of concentration of the reactive anion.
- Machacek, Vladimir,Svobodova, Gabriela,Sterba, Vojeslav
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p. 140 - 155
(2007/10/02)
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- Synthesis of Optically Active Spirohydantoins by Asymmetric Induction. Hydantoin Formation from Amino Nitriles and Chlorosulfonyl Isocyanate
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Conversion of 6-chloro- or 6-fluoro-2,3-dihydro-4H-1-benzopyran-4-one with optically active (S)-α-methylbenzylamine in the presence of TiCl4 to the ketimine followed by treatment in EtOH with HCN gas gives excellent yields of crystalline, enantiomerically pure (4S)-4-cyano-2,3-dihydro-6-chloro(or 6-fluoro)-4--4H-1-benzopyran.These sterically hindered amino nitriles react smoothly with chlorosulfonyl isocyanate to give, after hydrolysis, the hydantoins (4S)-2,3-dihydro-6-chloro(or 6-fluoro)-3'-spiro-2',5'-dione.The α-methylbenzyl groups can be removed by aqueous HBr/acetic acid to give the unprotected spirohydantoins.
- Sarges, Reinhard,Howard, Harry R.,Kelbaugh, Paul R.
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p. 4081 - 4085
(2007/10/02)
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- Photo-oxidation of Oxazolidones and Hydantoins in the Presence of Benzophenone
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Irradiation in the presence of benzophenone and oxygen of nitrogen-containing heterocycles having an NCO group yields products arising out of regioselective oxidation α to the nitrogen atom.Direct irradiation (in the absence of benzophenone and oxygen) of 5-methyl- and 5,5-dimethyl-hydantoins yields allophanates.The first step of this reaction involves the homolysis of the C(4) - C(5) bond of the hydantoin.
- Gramain, Jean-Claude,Remuson, Roland
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p. 2341 - 2346
(2007/10/02)
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