655224-18-3Relevant academic research and scientific papers
Enantioseletive Fluorination of 3-Functionalized Oxindoles Using Electron-rich Amino Urea Catalyst
Jiang, Xiaojian,Wang, Haitao,He, Haoquan,Wang, Wei,Wang, Yuqiang,Ke, Zhihai,Yeung, Ying-Yeung
supporting information, p. 4710 - 4714 (2018/11/10)
An enantioselective fluorination of 3-functionalized oxindoles using electron-rich amino urea catalyst is described. Various 3-functionalized 3-fluoro-2-oxindoles were obtained in good yields and enantio-selectivity. The resulting enantioenriched 3-methylene nitrile 3-fluoro-2-oxindole product was found to inhibit indoleamine 2,3-dioxygenase considerably. (Figure presented.).
Highly enantioselective fluorination of unprotected 3-substituted oxindoles: One-step synthesis of BMS 204352 (MaxiPost)
Li, Jun,Cai, Yunfei,Chen, Weiliang,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
, p. 9148 - 9155,8 (2012/12/12)
The catalytic enantioselective fluorination of N-H-free 3-substituted oxindoles was accomplished by a Sc(III)/N,N′-dioxide complex. Under mild reaction conditions, a series of 3-aryl- and 3-alkyl-3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) and enantioselectivities (up to 99% ee) by using N-fluorobisbenzenesulfonimide (NFSI) as the fluorination agent. MaxiPost was synthesized efficiently in 81% yield with 96% ee.
Highly enantioselective fluorination of unprotected 3-substituted oxindoles: One-step synthesis of BMS 204352 (MaxiPost)
Li, Jun,Cai, Yunfei,Chen, Weiliang,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
, p. 9148 - 9155 (2013/01/15)
The catalytic enantioselective fluorination of N-H-free 3-substituted oxindoles was accomplished by a Sc(III)/N,N′-dioxide complex. Under mild reaction conditions, a series of 3-aryl- and 3-alkyl-3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) and enantioselectivities (up to 99% ee) by using N-fluorobisbenzenesulfonimide (NFSI) as the fluorination agent. MaxiPost was synthesized efficiently in 81% yield with 96% ee.
CYCLOHEXYL AMIDE DERIVATIVES AS CRF RECEPTOR ANTAGONISTS
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Page/Page column 89, (2016/02/02)
There are described cydohexyl amide derivatives useful as corticotropin releasing factor (CRF) receptor antagonists
New approaches to enantioselective fluorination: Cinchona alkaloids combinations and chiral ligands/metal complexes
Shibata, Norio,Ishimaru, Takehisa,Nakamura, Shuichi,Toru, Takeshi
, p. 469 - 483 (2008/01/03)
The selective construction of carbon-fluorine bonds is of great interest to medicinal chemists because the replacement of a hydrogen or an oxygen atom with a fluorine atom in biologically active molecules can confer the molecules with improved physicochem
Ionic liquids as solvents of choice for electrophilic fluorination: Fluorination of indoles by F-TEDA-BF4
Baudoux, Jér?me,Salit, Anne-Frédérique,Cahard, Dominique,Plaquevent, Jean-Christophe
, p. 6573 - 6574 (2007/10/03)
Selectfluor was shown to be soluble in ionic liquid, thus allowing the 'green' electrophilic fluorination of indole compounds in high chemoselectivity and yields.
Enantioselective fluorination mediated by cinchona alkaloid derivatives/Selectfluor combinations: Reaction scope and structural information for N-fluorocinchona alkaloids
Shibata,Suzuki,Asahi,Shiro
, p. 7001 - 7009 (2007/10/03)
Cinchona-alkaloid/Selectfluor combinations efficiently fluorinate a variety of carbonyl compounds in a highly enantioselective manner to furnish chiral α-fluorocarbonyl compounds. The DHQB/Selectfluor combination is effective for the enantioselective fluo
A novel and efficient synthesis of 3-fluorooxindoles from indoles mediated by selectfluor
Takeuchi, Yoshio,Tarui, Takanao,Shibata, Norio
, p. 639 - 642 (2007/10/03)
(equation presented) Treatment of several 3-substituted indoles, including derivatives of tryptophan and serotonin, with commercially available Selectfluor in acetonitrile/ water furnished 3-substiuted 3-fluorooxindoles in good to high yields. Since 3-fluorooxindoles obtained are sterically similar to both oxindoles and 3-hydroxyoxindoles, they should be useful as probes for investigating the enzymatic mechanism of indole biosynthesis and metabolism.
