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5,5-Dialkyl-2,4-oxazolidinediones1,2

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    5,5-Dialkyl-2,4-oxazolidinediones1,2
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    Cite this: J. Am. Chem. Soc. 1941, 63, 9, 2376–2379
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    https://doi.org/10.1021/ja01854a019
    Published September 1, 1941
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    This article is cited by 27 publications.

    1. Seiya Uema, Nao Kojima, Tohru Yamada. Silver-catalyzed carbon dioxide incorporation into propargylic amides. Chemistry Letters 2024, 53 (3) https://doi.org/10.1093/chemle/upae001
    2. Wei Yi, Xing‐Xiao Fang, Qing‐Yun Liu, Gong‐Qing Liu. Metal‐Free Synthesis of Oxazolidine‐2,4‐diones and 3,3‐Disubstituted Oxindoles via ICl‐Induced Cyclization. European Journal of Organic Chemistry 2018, 2018 (47) , 6671-6681. https://doi.org/10.1002/ejoc.201801250
    3. Rajib Maity, Sandip Naskar, Kanchan Mal, Sandipa Biswas, Indrajit Das. Direct Access to 2‐Thioxooxazolidin‐4‐ones and Oxazolidine‐2,4‐diones from α‐Keto Thioesters through Thiolate Transfer. Advanced Synthesis & Catalysis 2017, 359 (24) , 4405-4410. https://doi.org/10.1002/adsc.201701020
    4. Kyriakos C. Prousis, John Markopoulos, Vickie Mckee, Olga Igglessi-Markopoulou. An efficient synthetic approach towards fully functionalized tetronic acids: the use of 1,3-dioxolane-2,4-diones as novel protected-activated synthons of α-hydroxy acids. Tetrahedron 2015, 71 (45) , 8637-8648. https://doi.org/10.1016/j.tet.2015.09.017
    5. Guido Galliani, Bruno Rindone, Ricardo Suarez-Bertoa, Francesco Saliu, Alberto Terraneo. Stereoselective Addition of Grignard Reagents and Lithium Alkyls onto 3,5-Disubstituted-1,3-oxazolidine-2,4-diones. Synthetic Communications 2013, 43 (5) , 749-757. https://doi.org/10.1080/00397911.2011.609301
    6. Yue H. Li, Li Zhang, Pei-San Tseng, Yongliang Zhang, Yu Jin, Jingkang Shen, Jian Jin. A facile one-pot synthesis of 3-unsubstituted-2,4-oxazolidinediones via in situ generation of carbamates from α-hydroxyesters using trichloroacetyl isocyanate. Tetrahedron Letters 2009, 50 (7) , 790-792. https://doi.org/10.1016/j.tetlet.2008.11.124
    7. Katsumi Iida, Takeshi Chiyoda, Ryo Hirasawa, Akiko Iwata, Masahiro Kajiwara. Synthesis of 13 C‐labelled compounds having a urea unit, and observation of 13 C‐isotope effect in their infrared spectra. Journal of Labelled Compounds and Radiopharmaceuticals 1997, 39 (1) , 69-77. https://doi.org/10.1002/(SICI)1099-1344(199701)39:1<69::AID-JLCR941>3.0.CO;2-#
    8. Yukio Hitotsuyanagi, Yoshitatsu Ichihara, Koichi Takeya, Hideji Itokawa. Synthesis of 4-Oxa-2-azapodophyllotoxin, a novel analog of the antitumor lignan podophyllotoxin. Tetrahedron Letters 1994, 35 (50) , 9401-9402. https://doi.org/10.1016/S0040-4039(00)78553-4
    9. Franz Effenberger, Brigitte Hörsch, Franz Weingart, Thomas Ziegler, Stefan Kühner. Enzyme-catalyzed synthesis or (R)-ketone-cyanohydrins and their hydrolysis to (R)-α-hydroxy-α-methyl-carboxylic acids. Tetrahedron Letters 1991, 32 (23) , 2605-2608. https://doi.org/10.1016/S0040-4039(00)78796-X
    10. Satoshi Inoki, Koji Kato, Shigeru Isayama, Teruaki Mukaiyama. A New and Facile Method for the Direct Preparation of α-Hydroxycarboxylic Acid Esters from α,β-Unsaturated Carboxylic Acid Esters with Molecular Oxygen and Phenylsilane Catalyzed by Bis(dipivaloylmethanato)manganese(II) Complex. Chemistry Letters 1990, 19 (10) , 1869-1872. https://doi.org/10.1246/cl.1990.1869
    11. Gary L. Jones. Anticonvulsant potency and toxicity of 5,5‐diphenyl‐2,4‐oxazolidinedione. Drug Development Research 1990, 21 (1) , 19-27. https://doi.org/10.1002/ddr.430210103
    12. J. Elks, C. R. Ganellin. D. 1990, 344-475. https://doi.org/10.1007/978-1-4757-2085-3_4
    13. Minoru Maeda, Yoshihiko Tatsuki, Toshimitsu Fukumura, Masaharu Kojima. Synthesis of 5‐fluoroalkyl‐5‐methyloxazolidine‐2,4‐diones and their 18 F‐labeled analogs as potential indicators of tissue pH. Journal of Labelled Compounds and Radiopharmaceuticals 1989, 27 (5) , 553-563. https://doi.org/10.1002/jlcr.2580270508
    14. M. Berridge, D. Comar, D. Roeda, A. Syrota. Synthesis and in vivo characteristics of [2-11C]5,5-dimethyloxazolidine-2,4-dione (DMO). The International Journal of Applied Radiation and Isotopes 1982, 33 (8) , 647-651. https://doi.org/10.1016/0020-708X(82)90064-3
    15. Egon Fahr, Ehrfried Büttner, Karl‐Heinz Keil, Jürgen Markert, Franz Scheckenbach, Reinhard Thiedemann, Johannes Fontaine. Azomethin‐imine durch Umsetzung von Diphenylketen mit Azodicarbonsäureestern. Liebigs Annalen der Chemie 1981, 1981 (8) , 1433-1444. https://doi.org/10.1002/jlac.198119810814
    16. Julius A. Vida, Elisabeth H. Gerry. Cyclic Ureides. 1977, 151-291. https://doi.org/10.1016/B978-0-12-721840-3.50011-8
    17. M. Makosza, T. Goetzen. SYNTHESIS OF PURE ARYLKETONE CYANOHYDRINS AND ARYLKETONES FROM AROMATIC ALDEHYDES. Organic Preparations and Procedures International 1973, 5 (5) , 203-207. https://doi.org/10.1080/00304947309356843
    18. T.P. Karpetsky, E.H. White. The synthesis of cypridina etioluciferamine and the proof of structure of cypridina luciferin. Tetrahedron 1973, 29 (23) , 3761-3773. https://doi.org/10.1016/0040-4020(73)80193-0
    19. D Sardini, A Marzo. Gas chromatographic evaluation of 5,5-dimethyl-2,4-oxazolidinedione ( dmo ) for determination of intracellular pH. Journal of Pharmacy and Pharmacology 1969, 21 (7) , 477-478. https://doi.org/10.1111/j.2042-7158.1969.tb08296.x
    20. A. Marzo, D. Sardini. Quantitative gas chromatographic determination of 5,5-dimethyl-2,4-oxazolidinedione. Journal of Chromatography A 1969, 44 , 611-613. https://doi.org/10.1016/S0021-9673(01)92585-3
    21. M. Pianka. Organophosphorus compounds. VI.—Structure and activity of certain 4‐(diethoxyphosphinothiomethyl) 4 H 1,3,4‐oxadiazoline‐5‐thiones, of certain 4‐diethoxyphosphinothioylthiomethyl‐thiazoles, and related compounds. Journal of the Science of Food and Agriculture 1968, 19 (8) , 475-480. https://doi.org/10.1002/jsfa.2740190814
    22. Hans Beyer, Rudolf Spörl. Über die Synthese von 2‐Benzylidenhydrazono‐oxazolidonen‐(4). Chemische Berichte 1966, 99 (9) , 2719-2724. https://doi.org/10.1002/cber.19660990902
    23. Thomas C. Butler, Jack D. Davidson. Synthesis of 5,5-Dimethyl-2,4-oxazolidinedione-2-C14 (DMO-2-C14). Journal of Pharmaceutical Sciences 1963, 52 (11) , 1110-1111. https://doi.org/10.1002/jps.2600521123
    24. A. Spinks, W.S. Waring. 6 Anticonvulsant Drugs. 1963, 261-331. https://doi.org/10.1016/S0079-6468(08)70120-6
    25. Lemont B. Kier, Devindra Dhawan. Synthesis of Sydnones as Potential Therapeutic Agents. Journal of Pharmaceutical Sciences 1962, 51 (11) , 1058-1061. https://doi.org/10.1002/jps.2600511110
    26. E. Testa, R. Ettorre. Fünfgliedrige, pharmakologisch wirksame Heterocyclen. Archiv der Pharmazie 1957, 290 (11) , 532-536. https://doi.org/10.1002/ardp.19572901105
    27. Frederick A. Fuhrman, John Field. The effect of propazone on the metabolism of rat cerebral cortex in vitro. Journal of Cellular and Comparative Physiology 1942, 19 (3) , 351-359. https://doi.org/10.1002/jcp.1030190310
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    Cite this: J. Am. Chem. Soc. 1941, 63, 9, 2376–2379
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja01854a019
    Published September 1, 1941
    Request reuse permissions

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