Synthesis of Isoxazolines and Isoxazoles via Metal-Free Desulfitative Cyclization

被引:7
作者
Cheng, Jiaxin [1 ]
Yang, Ze [1 ]
Li, Yuansheng [1 ]
Xi, Yulan [1 ]
Sun, Qiu [2 ]
He, Ling [1 ]
机构
[1] Sichuan Univ, West China Sch Pharm, Dept Med Chem, Chengdu 610041, Sichuan, Peoples R China
[2] Sichuan Univ, West China Med Ctr, Chengdu 610041, Sichuan, Peoples R China
来源
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 12期
基金
美国国家科学基金会;
关键词
isoxazolines; isoxazoles; desulfurization; radical cyclization; tandem reaction; AEROBIC OXIDATIVE AMINATION; C-H BONDS; NITRILE OXIDES; INTERMOLECULAR AMINATION; REGIOSELECTIVE SYNTHESIS; OXIMES; ALKENES; AMIDATION; EFFICIENT; POLYMERIZATION;
D O I
10.1055/s-0037-1609480
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel, one-pot reaction for the synthesis of isoxazolines and isoxazoles is developed via a cascade process under metal-free conditions. The approach involves the formation of intramolecular C-N and C-O bonds and intermolecular C-C bonds from aromatic alkenes or alkynes and N -hydroxysulfonamides using hypervalent iodine(VII) and iodine as the oxidant. Activation of C-H and C-C bonds/construction of C-O bonds/elimination of SO (2) /C-N bond formation is achieved in sequence in the reaction system.
引用
收藏
页码:2385 / 2393
页数:9
相关论文
共 75 条
  • [71] Synthesis of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of tomentosin
    Zaki, Mohamed
    Oukhrib, Abdelouahd
    Akssira, Mohamed
    Berteina-Raboin, Sabine
    [J]. RSC ADVANCES, 2017, 7 (11): : 6523 - 6529
  • [72] Controlled/"living" radical precipitation polymerization: A versatile polymerization technique for advanced functional polymers
    Zhang, Huiqi
    [J]. EUROPEAN POLYMER JOURNAL, 2013, 49 (03) : 579 - 600
  • [73] Trichloroisocyanuric Acid Promoted Cascade Cyclization/Trifluoromethylation of Allylic Oximes: Synthesis of Trifluoromethylated Isoxazolines
    Zhang, Weigang
    Su, Yingpeng
    Wang, Ke-Hu
    Wu, Lili
    Chang, Bingbing
    Shi, Ya
    Huang, Danfeng
    Hu, Yulai
    [J]. ORGANIC LETTERS, 2017, 19 (02) : 376 - 379
  • [74] Insect γ-Aminobutyric Acid Receptors and Isoxazoline Insecticides: Toxicological Profiles Relative to the Binding Sites of [3H]Fluralaner, [3H]-4′-Ethynyl-4-n-propylbicycloorthobenzoate, and [3H]Avermectin
    Zhao, Chunqing
    Casida, John E.
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2014, 62 (05) : 1019 - 1024
  • [75] TEMPO-Mediated Aliphatic C-H Oxidation with Oximes and Hydrazones
    Zhu, Xu
    Wang, Yi-Feng
    Ren, Wei
    Zhang, Feng-Lian
    Chiba, Shunsuke
    [J]. ORGANIC LETTERS, 2013, 15 (13) : 3214 - 3217