Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water

Buyck Thomas; Pasche Delphine; Wang Qian; Zhu Jieping

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Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water

机译：异腈，苯基乙烯基硒酮和水的氧化偶联合成恶唑烷-2-酮

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Reaction of alkyl isocyanides, phenyl vinyl selenone, and water in the presence of a catalytic amount of Cs2CO3 afforded oxazolidin-2-ones in good yields. This unprecedented heteroannulation process created four chemical bonds in a single operation with the isocyano group acting formally as a polarized double bond and phenyl vinyl selenone as a latent 1,3-dipole. The phenylselenonyl group played a triple role as an electron-withdrawing group to activate the 1,4-addition, a leaving group, and a latent oxidant in this transformation.

机译：在催化量的Cs 2 CO 3存在下，烷基异氰化物，苯基乙烯基硒酮和水的反应以良好的产率提供了恶唑烷-2-酮。这种前所未有的异环过程在一次操作中产生了四个化学键，其中异氰基以正式形式作用为极化双键，苯基乙烯基硒酮作为潜在的1,3-偶极子。在该转变中，苯基硒壬基作为吸电子基团起三重作用，以激活1,4-加成，离去基团和潜在的氧化剂。

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《Chemistry: A European journal》 |2016年第7期|共4页
作者
Buyck Thomas; Pasche Delphine; Wang Qian; Zhu Jieping;
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正文语种 eng
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annulation; domino reactions; isocyanide; oxazolidinone; selenium;

机译：环化;多米诺反应;异氰化物;恶唑烷酮;硒;

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1. Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water [J] . Buyck Thomas, Pasche Delphine, Wang Qian, Chemistry: A European journal . 2016,第7期

机译：异腈，苯基乙烯基硒酮和水的氧化偶联合成恶唑烷-2-酮
2. Triple Role of Phenylselenonyl Group Enabled a One-Pot Synthesis of 1,3-Oxazinan-2-ones From α-lsocyanoacetates, Phenyl Vinyl Selenones, and Water [J] . Thomas Buyck, Qian Wang, Jieping Zhu Journal of the American Chemical Society . 2014,第32期

机译：苯基硒代壬基的三重作用实现了从α-异氰酸酯，苯基乙烯基硒酮和水的一锅法合成1,3-氧杂嗪酮-2-酮
3. Integrated One-Pot Synthesis of 1,3-Oxazinan-2-ones from Isocyanoacetates and Phenyl Vinyl Selenones [J] . Thomas Buyck, Qian Wang, Jieping Zhu Chimia . 2015,第4期

机译：由异氰基乙酸酯和苯基乙烯基硒酮一体合成一锅法合成1,3-氧杂嗪酮-2-酮
4. Synthesis and characterization of poly (phenyl vinyl sulfoxide) and its coolymers-a soluble precursor to polyacetylene [C] . Louis M.Leung, K-H. Tan, T.S.Lam, Pacific polymer conference preprints . 1999

机译：聚（苯基乙烯基磺氧化砜）及其致乙炔的可溶性前体的合成与表征
5. Synthesis of precursors for the photochemical generation of substituted fluorenyl, phenyl and vinyl allene oxides. [D] . Konecny, Mark W. 2009

机译：用于光化学生成取代芴基，苯基和乙烯基丙二烯氧化物的前体的合成。
6. Enantioselective Synthesis of Oxetanes Bearing All-Carbon Quaternary Stereocenters via Iridium Catalyzed Alcohol-Vinyl Epoxide C-C Coupling [O] . Dr. Yi-An Guo, Dr. Wonchul Lee, Prof. Michael J. Krische -1

机译：铱催化的醇-乙烯基环氧C-C偶联对映合成全碳四元立体中心的氧杂环丁烷
7. A Catalytic Synthesis of Thiosilanes and Silthianes: Palladium Nanoparticle-Mediated Cross-Coupling of Silanes with Thio Phenyl and Thio Vinyl Ethers through Selective Carbon-Sulfur Bond Activation [O] . -1

机译：硫醇和硅藻土的催化合成：钯纳米粒子介导通过选择性碳 - 硫粘合活化与硫酸噻唑烷基和硫乙烯基醚的硅烷的交联偶联
8. Palladium Catalyzed Coupling of F-Vinyl Zinc Reagents with Aryl Iodides. An Improved Synthesis of Alpha, Beta, Beta-Trifluorostyrenes and the Stereospecific Preparation of 1-Phenyl-F-Propenes [R] . Heinze, P. L., Burton, D. J. 1986

机译：钯催化F-乙烯基锌试剂与芳基碘化物的偶联。 α，β，β-三氟苯乙烯的改进合成及1-苯基-F-丙烯的立体特异性制备

Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water

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