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Journal articles on the topic 'Phenyloxazolidone'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

A., H. SIDDIQUI, VENKATESHWER RAO K., and VIJAYASENA REDDY K. "Synthesis of Steroidal Extranucleo N-Phenyloxazolidones of Androstane Series." Journal of Indian Chemical Society Vol. 65, Dec 1988 (1988): 850–51. https://doi.org/10.5281/zenodo.6089596.

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Department of Chemistry, Nizam College, Hyderabad-500 001 <em>Manuscript received 13 May 1988, accepted 23 August 1988</em> 17-Oxo-5-androsten-3\(\beta\)-yl acetate (1a) and 3\(\beta\) -chloro-17-oxo-5-androstene (2a) on reaction with hydrazine hydrate in alcoholic solution gave 5-androsten-17-hydrazone-3\(\beta\) -yl acetate (1b) and 3\(\beta\) -chloro-5-androsten-17-hydrazone (2b), respectively. The subsequent reaction of these 17-hydrazones (1b, 2b) with phenyl isocyanate in benzene solution afforded the corresponding 17-<em>N</em>-pbenylsemlcarbazone derivatives (1c, 2c

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2

Katritzky, Alan R., Justo Cobo-Domingo, Baozhen Yang, and Peter J. Steel. "Diastereoselective Synthesis of N-Substituted Ethyl 4-Phenyloxazolidine-2-carboxylates." Journal of Chemical Research 23, no. 2 (1999): 162–63. http://dx.doi.org/10.1177/174751989902300248.

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( S)-2-Phenylglycinol, ethyl glyoxylate, formaldehyde and benzotriazole formed stereospecifically ethyl (2 S,4 S)- N-(benzotriazol-1-yl)methyl-4-phenyloxazolidine-2-carboxylate (1) which was converted into chiral N-substituted oxazolidines, via regiospecific substitutions of the benzotriazolyl residue.

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3

Betz, Richard, and Peter Klüfers. "3-Phenyloxazolidin-2-one." Acta Crystallographica Section E Structure Reports Online 63, no. 12 (2007): o4922. http://dx.doi.org/10.1107/s1600536807061053.

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4

Lemoine, P., B. Viossat, P. G. Martin, and D. J. Aitken. "N,N'-Methylenebis[(S)-5-phenyloxazolidine]." Acta Crystallographica Section C Crystal Structure Communications 54, no. 7 (1998): 1036–38. http://dx.doi.org/10.1107/s010827019701562x.

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5

Pilotzi Xahuentitla, Hugo, Jesús Guadalupe Ortega Montes, Dino Hernán Gnecco Medina, Joel Luis Terán Vázquez, Emanuel Hernández Núñez, and Maria Laura Orea Flores. "Synthesis of Methyl 2-((4R)-3-Acryloyl-4-phenyloxazolidin-2-yl)acetates." Molbank 2024, no. 4 (2024): M1903. http://dx.doi.org/10.3390/m1903.

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The chiral oxazolidine moiety is an important core in asymmetric synthesis due to its ability to participate in various stereoselective chemical reactions and because it forms part of more complex and important active compounds. Therefore, in this letter we report a convenient diastereoselective and practical strategy for the synthesis of chiral methyl 2-((4R)-3-acryloyl-4-phenyloxazolidin-2-yl)acetates, starting from (R)-(–)-2-phenylglycinol and methyl propiolate, which were obtained via two simple chemical and stereoselective reactions.

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6

Abeer, Fauzi Al-Rubaye, Jawad Kadhim Mohanad, and Hadi Hameed Imad. "Phytochemical Profiles of Methanolic Seeds Extract of Cuminum cyminum using GC-MS Technique." International Journal of Current Pharmaceutical Review and Research 8, no. 2 (2017): 114–24. https://doi.org/10.5281/zenodo.12677798.

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The aims of this study were identify the chemical components as well as anti-microbial activities of the methanolic seedsextract of Cuminum cyminum. GC-MS analysis revealed the existence of the Benzene , 1,1'-oxybis[4-phenoxy- ,Stearyltrimethylammonium chloride , Benzenemethanol , 4-hydroxy-α-[1-methylamino)ethyl]-,(R*,S*)- , Quinolin2(1H)-one , 3,4,5,6,7,8-hexahydro-3-dimethylaminomethyl- , 5-Hepten-2-amine , N,6-dimethyl- , 2-Pentanone , 4-amino-4-methyl- , Benzedrex , α-Pinene , 10-(dimethylaminomethyl)- , Ethanamine ,2-(2,6-dimethylphenoxy)-N-methyl-, Ephedrine , 1-(1,4-cyclohe

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7

Katritzky, Alan R., Justo Cobo-Domingo, Baozhen Yang, and Peter J. Steel. "Diastereoselective Synthesis of N-Substituted Ethyl 4-Phenyloxazolidine-2-carboxylates." Journal of Chemical Research, no. 2 (1999): 162–63. http://dx.doi.org/10.1039/a807578f.

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8

Suárez-Castillo, Oscar R., Myriam Meléndez-Rodríguez, Luis E. Castelán-Duarte, et al. "Absolute configuration assignment of 3-oxindolylacetyl-4-phenyloxazolidinone derivatives." Tetrahedron: Asymmetry 22, no. 24 (2011): 2085–98. http://dx.doi.org/10.1016/j.tetasy.2011.11.018.

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9

Polyak, Felix, Tatiana Dorofeeva, and Gunar Zelchan. "Catalytic Hydrogenation of Chiral 2-(2-Furyl)-3,4-dimethyl-5-phenyloxazolidine." Synthetic Communications 25, no. 19 (1995): 2895–900. http://dx.doi.org/10.1080/00397919508011419.

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10

García-Merinos, J. Pablo, Heraclio López-Ruiz, Yliana López, and Susana Rojas-Lima. "O-EthylS-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyloxazolidin-3-yl]propan-2-yl} carbonodithioate." Acta Crystallographica Section E Structure Reports Online 70, no. 5 (2014): o584—o585. http://dx.doi.org/10.1107/s1600536814007636.

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In the title compound, C15H17NO4S2, synthesized by addition ofO-ethylxanthic acid potassium salt to a diastereomeric mixture of (4R)-3-(2-chloropropanoyl)-4-phenyloxazolidin-2-one, the oxazolidinone ring has a twist conformation on the C—C bond. The phenyl ring is inclined to the mean plane of the oxazolidinone ring by 76.4 (3)°. In the chain the methine H atom is involved in a C—H...S and a C—H...O intramolecular interaction. In the crystal, molecules are linked by C—H...π interactions, forming chains along [001]. TheSconfiguration at the C atom to which the xanthate group is attached was det

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11

Katritzky, Alan R., Justo Cobo-Domingo, Baozhen Yang, and Peter J. Steel. "ChemInform Abstract: Diastereoselective Synthesis of N-Substituted Ethyl 4-Phenyloxazolidine-2-carboxylates." ChemInform 30, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199934150.

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12

POLYAK, F., T. DOROFEEVA, and G. ZELCHAN. "ChemInform Abstract: Catalytic Hydrogenation of Chiral 2-(2-Furyl)-3,4-dimethyl-5- phenyloxazolidine." ChemInform 26, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199547080.

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13

Eames, Jason, Najla Al Shaye, Tom Broughton, and Elliot Coulbeck. "Resolution of Pentafluorophenyl Active Esters Using (S)-4-Phenyloxazolidin-2-thione." Synlett 2009, no. 06 (2009): 960–64. http://dx.doi.org/10.1055/s-0028-1088218.

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14

Wu, Yikang, Yong-Qing Yang, and Qi Hu. "A Facile Access to Chiral 4-Isopropyl-, 4-Benzyl-, and 4-Phenyloxazolidine-2-thione." Journal of Organic Chemistry 69, no. 11 (2004): 3990–92. http://dx.doi.org/10.1021/jo049799d.

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15

Sugiyama, Shigeo, Keitaro Ishii, and Satoshi Arai. "Stereoselective Gram-Scale Synthesis of (S)-5,5-Dimethyl-4-phenyloxazolidin-2-one." HETEROCYCLES 65, no. 1 (2005): 149. http://dx.doi.org/10.3987/com-04-10220.

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16

Chavda, Sameer, Jason Eames, Majid Motevalli, and Nela Malatesti. "(–)-(4R,5S)-4-Methyl-3-[2(S)-phenoxypropionyl]-5-phenyloxazolidin-2-one." Acta Crystallographica Section E Structure Reports Online 62, no. 9 (2006): o4043—o4045. http://dx.doi.org/10.1107/s1600536806031850.

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17

Coumbarides, Gregory S., Jason Eames, Majid Motevalli, Nela Malatesti, and Yonas Yohannes. "(+)-(4R,5S)-4-Methyl-3-[2(R)-phenoxypropionyl]-5-phenyloxazolidin-2-one." Acta Crystallographica Section E Structure Reports Online 62, no. 9 (2006): o4041—o4042. http://dx.doi.org/10.1107/s1600536806031862.

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18

Saviozzi, Chiara, Sara Stocchetti, Giulio Bresciani, Lorenzo Biancalana, Guido Pampaloni, and Fabio Marchetti. "Adding Diversity to Diiron Aminocarbyne Complexes with Amine Ligands." Inorganics 11, no. 3 (2023): 91. http://dx.doi.org/10.3390/inorganics11030091.

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The reactions of the diiron aminocarbyne complexes [Fe2Cp2(NCMe)(CO)(μ-CO){μ-CN(Me)(R)}]CF3SO3 (R = Me, 1aNCMe; R = Cy, 1bNCMe), freshly prepared from the tricarbonyl precursors 1a–b, with primary amines containing an additional function (i.e., alcohol or ether) proceeded with the replacement of the labile acetonitrile ligand and formation of [Fe2Cp2(NH2CH2CH2OR’)(CO)(μ-CO){μ-CN(Me)(R)}]CF3SO3 (R = Me, R’ = H, 2a; R = Cy, R’ = H, 2b; R = Cy, R’ = Me, 2c) in 81–95% yields. The diiron-oxazolidinone conjugate [Fe2Cp2(NH2OX)(CO)(μ-CO){μ-CN(Me)2}]CF3SO3, 3, was prepared from 1a, 3-(2-aminoethyl)-5-

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19

Tessier, Arnaud, Julien Pytkowicz, and Thierry Brigaud. "2-Trifluoromethyl-2-methyl-4-phenyloxazolidine: A new chiral auxiliary for highly diastereoselective enolate alkylation." Journal of Fluorine Chemistry 134 (February 2012): 122–27. http://dx.doi.org/10.1016/j.jfluchem.2011.02.020.

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20

Nie, Lei, Rui Yang, Juan Wang, Sheng-Jiao Yan, and Jun Lin. "(R)-3-[(E)-3-(2-Furyl)acryloyl]-5,5-dimethyl-4-phenyloxazolidin-2-one." Acta Crystallographica Section E Structure Reports Online 62, no. 10 (2006): o4493—o4494. http://dx.doi.org/10.1107/s1600536806036890.

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21

Dorn, Helmut, and Dieter Arndt. "3-Methyl-5-(1,2,3,4-tetrahydroxy-butyl)-2-phenyloxazolidine aus Benzaldehyd und 1-Methylamino-1-desoxy-zuckeralkoholen." Zeitschrift für Chemie 11, no. 8 (2010): 306–7. http://dx.doi.org/10.1002/zfch.19710110806.

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22

Lou, Bih-Show, Guigen Li, Feng-Di Lung, and Victor J. Hruby. "NMR Investigation of Asymmetric Conjugate Additions Using Chiral 4-Phenyloxazolidinone as a Mechanistic Probe." Journal of Organic Chemistry 60, no. 17 (1995): 5509–14. http://dx.doi.org/10.1021/jo00122a033.

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23

Marchand-Brynaert, Jacqueline, Jean-Christophe Monbaliu, and Bernard Tinant. "Reactivity of (R)-4-Phenyloxazolidin-2-thione Chiral Auxiliary: From Deprotection to Heterocyclic Interconversion." HETEROCYCLES 75, no. 10 (2008): 2459. http://dx.doi.org/10.3987/com-08-11410.

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24

Chavda, Sameer, Jason Eames, Anthony Flinn, Majid Motevalli, and Nela Malatesti. "(–)-(4R,5S)-4-Methyl-3-[2(R)-(4-methylphenyl)propionyl]-5-phenyloxazolidin-2-one." Acta Crystallographica Section E Structure Reports Online 62, no. 9 (2006): o4037—o4038. http://dx.doi.org/10.1107/s1600536806031825.

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25

Chavda, Sameer, Jason Eames, Anthony Flinn, Majid Motevalli, and Nela Malatesti. "(–)-(4R,5S)-3-[2(R)-(4-Chlorophenyl)propionyl]-4-methyl-5-phenyloxazolidin-2-one." Acta Crystallographica Section E Structure Reports Online 62, no. 9 (2006): o4039—o4040. http://dx.doi.org/10.1107/s1600536806031837.

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26

Coumbarides, Gregory S., Marco Dingjan, Jason Eames, Majid Motevalli, and Nela Malatesti. "(+)-(4R,5S)-3-[2(S)-(4-Isobutylphenyl)propionyl]- 4-methyl-5-phenyloxazolidin-2-one." Acta Crystallographica Section E Structure Reports Online 62, no. 9 (2006): o4035—o4036. http://dx.doi.org/10.1107/s1600536806031849.

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27

Anderson, Alexander E., Kate L. Edler, Raleigh W. Parrott, Shawn R. Hitchcock, and Gregory M. Ferrence. "(6S)-2-tert-Butyl-6-[(4S,5R)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol." Acta Crystallographica Section E Structure Reports Online 66, no. 4 (2010): o902—o903. http://dx.doi.org/10.1107/s1600536810009190.

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28

Yang, Rui, Lei Nie, Mei-Su Zhang, Juan Wang, and Jun Lin. "(3′R,4S)-3-(3′-Cyclohexyl-3′-phenylpropionyl)-5,5-dimethyl-4-phenyloxazolidin-2-one." Acta Crystallographica Section E Structure Reports Online 62, no. 9 (2006): o3618—o3619. http://dx.doi.org/10.1107/s1600536806016035.

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29

Besson, Laure, Marc Le Bail, David J. Aitken, Henri-Philippe Husson, Françoise Rose-Munch та Eric Rose. "An enantiomerically pure tricyclic isoindoline system by cyclisation of tricarbonyl[η6-(R)-N-cyanomethyl-4-phenyloxazolidine]chromium". Tetrahedron Letters 37, № 19 (1996): 3307–8. http://dx.doi.org/10.1016/0040-4039(96)00520-5.

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30

Tessier, Arnaud, Julien Pytkowicz, and Thierry Brigaud. "ChemInform Abstract: 2-Trifluoromethyl-2-methyl-4-phenyloxazolidine: A New Chiral Auxiliary for Highly Diastereoselective Enolate Alkylation." ChemInform 43, no. 28 (2012): no. http://dx.doi.org/10.1002/chin.201228021.

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31

Zhang, Yang, Yan Zhang, Sheng Xie, Mingdi Yan, and Olof Ramström. "Lipase-catalyzed kinetic resolution of 3-phenyloxazolidin-2-one derivatives: Cascade O- and N-alkoxycarbonylations." Catalysis Communications 82 (July 2016): 11–15. http://dx.doi.org/10.1016/j.catcom.2016.04.009.

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32

Koyanagi, Takaoki, Kate L. Edler, Raleigh W. Parrott, Shawn R. Hitchcock, and Gregory M. Ferrence. "(6R)-2-tert-Butyl-6-[(4R,5S)-3-isopropyl-4-methyl-5-phenyloxazolidin-2-yl]phenol." Acta Crystallographica Section E Structure Reports Online 66, no. 4 (2010): o898—o899. http://dx.doi.org/10.1107/s1600536810009591.

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33

Belokoń, Yu N., Yu N. Bubnov, T. D. Churkina, et al. "Diastereoselective bromination of(R)-N-cinnamoyl-4-phenyloxazolidin-2-one in the presence of Lewis acids." Russian Chemical Bulletin 46, no. 5 (1997): 982–89. http://dx.doi.org/10.1007/bf02496131.

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34

Doyle, Michael P., William R. Winchester, Marina N. Protopopova, et al. "Tetrakis[(4S)-4-phenyloxazolidin-2-one]dirhodium(II) and Its Catalytic Applications for Metal Carbene Transformations." Helvetica Chimica Acta 76, no. 6 (1993): 2227–35. http://dx.doi.org/10.1002/hlca.19930760606.

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35

BESSON, L., M. LE BAIL, D. J. AITKEN, H. P. HUSSON, F. ROSE-MUNCH та E. ROSE. "ChemInform Abstract: An Enantiomerically Pure Tricyclic Isoindoline System by Cyclization of Tricarbonyl(η6-(R)-N-cyanomethyl-4-phenyloxazolidine)chromium." ChemInform 27, № 33 (2010): no. http://dx.doi.org/10.1002/chin.199633139.

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36

Campbell, Ian Sean, Kate L. Edler, Raleigh W. Parrott, Shawn R. Hitchcock, and Gregory M. Ferrence. "(6S)-2,4-Di-tert-butyl-6-[(4S,5R)-3-isopropyl-4-methyl-5-phenyloxazolidin-2-yl]phenol." Acta Crystallographica Section E Structure Reports Online 66, no. 4 (2010): o900—o901. http://dx.doi.org/10.1107/s1600536810009074.

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37

Feroci, Marta, Achille Inesi, Monica Orsini, and Laura Palombi. "Electrochemical Carboxylation ofN-(2-Bromopropionyl)-4R- phenyloxazolidin-2-one: An Efficient Route to Unsymmetrical Methylmalonic Ester Derivatives." Organic Letters 4, no. 16 (2002): 2617–20. http://dx.doi.org/10.1021/ol025939z.

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38

Pyne, Stephen G., Javad Safaei-G., and Fiona Koller (in part). "Exo-Diastereoselective 1,3-dipolar cycloadditions of azomethine ylides to (2R)-3-Benzoyl-4-methylene-2-phenyloxazolidin-5-one." Tetrahedron Letters 36, no. 14 (1995): 2511–14. http://dx.doi.org/10.1016/0040-4039(95)00294-m.

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39

Lucet, Denis, Philippe Heyse, Arnaud Gissot, Thierry Le Gall, and Charles Mioskowski. "Synthesis of the Diastereomers of Dethiobiotin Using the Conjugate Addition of 4-Phenyloxazolidin-2-one to a Nitroalkene." European Journal of Organic Chemistry 2000, no. 21 (2000): 3575–79. http://dx.doi.org/10.1002/1099-0690(200011)2000:21<3575::aid-ejoc3575>3.0.co;2-r.

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40

BELOKON', YU N., YU N. BUBNOV, T. D. CHURKINA, et al. "ChemInform Abstract: Diastereoselective Bromination of (R)-N-Cinnamoyl-4-phenyloxazolidin-2- one in the Presence of Lewis Acids." ChemInform 28, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.199743038.

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41

DOYLE, M. P., W. R. WINCHESTER, M. N. PROTOPOPOVA, et al. "ChemInform Abstract: Tetrakis((4S)-4-phenyloxazolidin-2-one)dirhodium(II) and Its Catalytic Applications for Metal Carbene Transformations." ChemInform 24, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199352066.

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42

KANEMASA, S., K. ONIMURA, E. WADA, and J. TANAKA. "ChemInform Abstract: 2,2-Dimethyl-4-phenyloxazolidine and 2,2-Dimethyl-4,5- diphenylimidazolidine as New Chiral Auxiliaries. Applications to Asymmetric Nitrile Oxide Cycloadditions." ChemInform 23, no. 14 (2010): no. http://dx.doi.org/10.1002/chin.199214073.

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43

Monbaliu, Jean-Christophe, Raphaël Robiette, Daniel Peeters, and Jacqueline Marchand-Brynaert. "(R)-4-phenyloxazolidin-2-thione: an efficient chiral auxiliary for [4+2] cycloaddition of 1-aminodiene and activated phosphonodienophiles." Tetrahedron Letters 50, no. 12 (2009): 1314–17. http://dx.doi.org/10.1016/j.tetlet.2009.01.036.

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44

TARAROV, V. I., T. F. SAVEL'EVA, YU T. STRUCHKOV, A. P. PISAREVSKII, N. I. RAEVSKII та YU N. BELOKON'. "ChemInform Abstract: Mechanism of Kharash Reaction Catalyzed by Fe(CO)5. Part 1. Stereochemistry of BrCCl3 Addition to (R)-3-(E)-Cinnamoyl-4- phenyloxazolidin-2-one, (R)-3-(E)-Acryloyl-4-phenyloxazolidin-2-one and Their π-Complexes with Fe(CO)4." ChemInform 27, № 37 (2010): no. http://dx.doi.org/10.1002/chin.199637041.

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45

Bakhtiar, R., C. E. C. A. Hop, and R. B. Walker. "Effect of Cyclodextrins on the Hydrolysis of an Oxazolidine Prodrug of (1R,2S)-(−)-Ephedrine-cis-2-(4-Methoxyphenyl)-3,4-dimethyl-5-phenyloxazolidine." Rapid Communications in Mass Spectrometry 11, no. 6 (1997): 598–602. http://dx.doi.org/10.1002/(sici)1097-0231(199704)11:6<598::aid-rcm903>3.0.co;2-v.

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46

Abed Badrian, Manouchehr Mamaghani, Khalil Tabatabaeian, and Hassan Valizadeh. "Asymmetric Induction in Darzens Condensation by Means of (R)-5,5- Dimethyl-4-Phenyloxazolidin-2-One as an Effective Chiral Auxiliary." Letters in Organic Chemistry 4, no. 4 (2007): 228–31. http://dx.doi.org/10.2174/157017807781024327.

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47

Romanenko, Vadim D., Claire Thoumazet, Vincent Lavallo, Fook S. Tham, and Guy Bertrand. "Synthesis and reactivity of a stable crystalline diastereomerically pure trifluoromethanesulfinic acid derivative: (S)-(−)-1-trifluoromethylsulfinyl-(R)-4-phenyloxazolidin-2-one." Chem. Commun., no. 14 (2003): 1680–81. http://dx.doi.org/10.1039/b303574c.

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48

PYNE, S. G., J. SAFAEI-G., and F. KOLLER. "ChemInform Abstract: exo-Diastereoselective 1,3-Dipolar Cycloadditions of Azomethine Ylides to (2R)-3-Benzoyl-4-methylene-2-phenyloxazolidin-5-one." ChemInform 26, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199531208.

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49

Lucet, Denis, Philippe Heyse, Arnaud Gissot, Thierry Le Gall, and Charles Mioskowski. "ChemInform Abstract: Synthesis of the Diastereomers of Dethiobiotin Using the Conjugate Addition of 4-Phenyloxazolidin-2-one to a Nitroalkene." ChemInform 32, no. 6 (2001): no. http://dx.doi.org/10.1002/chin.200106197.

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50

Feroci, Marta, Achille Inesi, Monica Orsini, and Laura Palombi. "ChemInform Abstract: Electrochemical Carboxylation of N-(2-Bromopropionyl)-4R-phenyloxazolidin-2-one: An Efficient Route to Unsymmetrical Methylmalonic Ester Derivatives." ChemInform 33, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.200249121.

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