HYPERVALENT IODINE-CATALYZED CYCLOADDITION OF NITRILE OXIDES TO ALKENES

被引：24
|
作者：
Xiang, Changbin [1 ]
Li, Tingting [1 ]
Yan, Jie [1 ]
机构：
[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310032, Zhejiang, Peoples R China
来源：
SYNTHETIC COMMUNICATIONS | 2014年 / 44卷 / 05期
关键词：
Catalytic reaction; cycloaddition; hypervalent iodine intermediate; iodobenzene; isoxazoline; HYDROXIMOYL CHLORIDES; POTENT INHIBITORS; BENZISOXAZOLES; ISOXAZOLINES; DERIVATIVES; OXIDATIONS; GENERATION; ALDOXIMES; CHEMISTRY; OXIMES;
D O I：
10.1080/00397911.2013.834364
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new and convenient method for preparation of isoxazolines was developed by a catalytic cycloaddition of nitrile oxides generated in situ from aldoximes to alkenes in the presence of a catalytic amount of iodobenzene. In this protocol, iodobenzene was first oxidized into the hypervalent iodine intermediate by m-chloroperbenzoic acid, which then transformed aldoximes into nitrile oxides, and a 1,3-dipolar cycloaddition of nitrile oxides to alkenes to provide the isoxazolines in moderate to good yields. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
引用
收藏
页码：682 / 688
页数：7
相关论文
共 50 条
  • [31] Iodine-Catalyzed Etherification of Morroniside
    Sunghwa, Fortunatus
    Sakurai, Hiroaki
    Saiki, Ikuo
    Koketsu, Mamoru
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2009, 57 (01) : 112 - 115
  • [32] IODINE-CATALYZED AROMATIZATION OF MENTHANES
    HO, TL
    CHEMISTRY & INDUSTRY, 1987, (08) : 295 - 296
  • [33] IODINE-CATALYZED IODINE EXCHANGE-REACTIONS
    KOROS, E
    ORBAN, M
    MAGYAR KEMIAI FOLYOIRAT, 1972, 78 (2-3): : 124 - &
  • [34] Iodine-Catalyzed Regioselective Sulfonylation of Quinoline N-Oxides with Sulfonyl Hydrazides
    Yu, Haiyang
    Pi, Chao
    Wang, Yong
    Cui, Xiuling
    Wu, Yangjie
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (01) : 124 - 130
  • [35] Cyclopropanation of alkenes using hypervalent iodine reagents
    Biland, AS
    Altermann, S
    Wirth, T
    ARKIVOC, 2003, : 164 - 169
  • [36] Intramolecular aminocyanation of alkenes promoted by hypervalent iodine
    Shen, Hang
    Deng, Qingfu
    Liu, Ruojuan
    Feng, Yangyang
    Zheng, Congke
    Xiong, Yan
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (09): : 1806 - 1811
  • [37] Ruthenium-Catalyzed Cycloaddition of Nitrile Oxides and Alkynes: Practical Synthesis of Isoxazoles
    Grecian, Scott
    Fokin, Valery V.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (43) : 8285 - 8287
  • [38] Cycloaddition of nitrile oxides to substituted vinylphosphonates
    Ye, Y
    Xu, GY
    Zheng, Y
    Liu, LZ
    HETEROATOM CHEMISTRY, 2003, 14 (04) : 309 - 311
  • [39] Cycloaddition of nitrile oxides to unsaturated phosphonates
    Department of Chemistry, Korea Adv. Inst. Sci. and Technol., 373-1, Kusong Dong, Yusong Gu, Taejon, 305-701, Korea, Republic of
    不详
    Synth. Commun., 20 (3621-3626):
  • [40] Cycloaddition of nitrile oxides to unsaturated phosphonates
    Lee, SY
    Lee, BS
    Lee, CW
    Oh, DY
    SYNTHETIC COMMUNICATIONS, 1999, 29 (20) : 3621 - 3626
12345