Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones with Hypervalent Iodine Reagents

被引：50
作者：
Matassini, Camilla [1 ]
Parmeggiani, Camilla [1 ,2 ,3 ]
Cardona, Francesca [1 ]
Goti, Andrea [1 ]
机构：
[1] Univ Florence, Dipartimento Chim Ugo Schiff Polo Sci & Tecnol, I-50019 Sesto Fiorentino, FI, Italy
[2] CNR, INO, I-50019 Sesto Fiorentino, FI, Italy
[3] LENS, I-50019 Sesto Fiorentino, FI, Italy
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 16期
关键词：
IODOXYBENZOIC ACID IBX; PYRROLINE N-OXIDES; ONE-POT SYNTHESIS; SECONDARY-AMINES; HYDROGEN-PEROXIDE; CATALYTIC-OXIDATION; NITRILE OXIDES; CYCLIC NITRONES; CYCLOADDITION; PYRROLIZIDINE;
D O I：
10.1021/acs.orglett.5b02029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Hypervalent iodine compounds are viable reagents for the oxidation of N,N-disubstituted hydroxylamines to the corresponding nitrones, with IBX performing best. The procedure is very simple and user-friendly and affords the target compounds with high efficiency and regioselectivity, highlighting IBX as the reagent of choice for preparation of aldonitrones from nonsymmetric hydroxylamines. Evidence for a mechanism involving nitrogen to iodine coordination has been collected.
引用
收藏
页码：4082 / 4085
页数：4
相关论文
共 49 条
  • [21] Hypervalent Iodine Mediated Efficient Solvent-Free Regioselective Halogenation and Thiocyanation of Fused N-Heterocycles
    Indukuri, Divakar Reddy
    Potuganti, Gal Reddy
    Alla, Manjula
    SYNLETT, 2019, 30 (13) : 1573 - 1579
  • [22] Hg cathode-free electrochemical detosylation of N,N-disubstituted p-toluenesulfonamides: mild, efficient, and selective removal of N-tosyl group
    Senboku, Hisanori
    Nakahara, Kazuo
    Fukuhara, Tsuyoshi
    Hara, Shoji
    TETRAHEDRON LETTERS, 2010, 51 (02) : 435 - 438
  • [23] Photoredox Catalysis Enables Decarboxylative Cyclization with Hypervalent Iodine(III) Reagents: Access to 2,5-Disubstituted 1,3,4-Oxadiazoles
    Li, Jian
    Lu, Xue-Chen
    Xu, Yue
    Wen, Jin-Xia
    Hou, Guo-Quan
    Liu, Li
    ORGANIC LETTERS, 2020, 22 (24) : 9621 - 9626
  • [24] Copper-Promoted Aerobic Oxidative [3+2] Cycloaddition Reactions of N,N-Disubstituted Hydrazines with Alkynoates: Access to Substituted Pyrazoles
    Zou, Xiaoying
    Zheng, Lvyin
    Zhuo, Xiaoya
    Zhong, Yumei
    Wu, Yingying
    Yang, Beining
    He, Qifang
    Guo, Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (04) : 2190 - 2206
  • [25] Hypervalent iodine(III)-induced methylene acetoxylation of 3-oxo-N-substituted butanamides
    Liu, Wei-Bing
    Chen, Cui
    Zhang, Qing
    Zhu, Zhi-Bo
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 1436 - 1440
  • [26] N-GLYCOSYLATION REACTION OF THIO-GLYCOSIDE USING HYPERVALENT IODINE(III) REAGENT
    Morimoto, Koji
    Yanase, Kana
    Ikeda, Takumi
    Uchikawa, Chihiro
    Kita, Yasuyuki
    Kajimoto, Tetsuya
    HETEROCYCLES, 2020, 101 (02) : 621 - 630
  • [27] Hypervalent Iodine(III)-Mediated Regioselective Cyanation of Quinoline N-Oxides with Trimethylsilyl Cyanide
    Xu, Feng
    Li, Yuqin
    Huang, Xin
    Fang, Xinjie
    Li, Zhuofei
    Jiang, Hongshuo
    Qiao, Jingyi
    Chu, Wenyi
    Sun, Zhizhong
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (03) : 520 - 525
  • [28] Two-pot synthesis of N,N-disubstituted 4H-3,1-benzothiazin-2-amines from aryl(2-isothiocyanatophenyl)methanones and secondary amines
    Kobayashi, Kazuhiro
    Kanbe, Yuuki
    TETRAHEDRON, 2011, 67 (50) : 9680 - 9684
  • [29] Syntheses of N-sulfonyl-N,N-disubstituted amidines via a three-component free-radical coupling reaction of tertiary amines and arenesulfoyl azides with terminal alkynes
    He XinWei
    Shang YongJia
    Hu JinSong
    Ju Kai
    Jiang Wei
    Wang SuFang
    SCIENCE CHINA-CHEMISTRY, 2012, 55 (02) : 214 - 222
  • [30] Hypervalent Iodine-Mediated Oxidative Rearrangement of N-H Ketimines: An Umpolung Approach to Amides
    Zhao, Zhenguang
    Peng, Zhiyuan
    Zhao, Yongli
    Liu, Hao
    Li, Chongnan
    Zhao, Junfeng
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (22) : 11848 - 11853
12345