Koser's Reagent Mediated Oxidation of Aldoximes: Synthesis of Isoxazolines by 1,3-Dipolar Cycloadditions

被引：2
|
作者：
Budhwan, Rajnish [1 ]
Rawat, Megha [1 ]
Peddinti, Rama Krishna [1 ]
机构：
[1] Indian Inst Technol Roorkee, Dept Chem, Roorkee 247667, Uttaranchal, India
来源：
SYNTHESIS-STUTTGART | 2023年 / 55卷 / 12期
关键词：
arylaldoximes; C-C and C-O bond formation; fused isoxazolines; heterocycles; hypervalent iodine; nitrile oxides; oxidation; ONE-POT SYNTHESIS; NITRILE OXIDES; FACILE SYNTHESIS; AQUEOUS-MEDIA; IODINE; GENERATION; OXIMES; DERIVATIVES; ALKENES; ANTICANCER;
D O I：
10.1055/s-0042-1752403
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal-and base-free, robust, and convenient approach for the synthesis of isoxazoline derivatives is reported. This protocol involves 1,3-dipolar cycloaddition between in situ generated nitrile oxides from the corresponding aldoximes using [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser's reagent) and maleimides, styrene and acrylonitrile. The described methodology is very attractive as it is operationally simple, has broad scope, and does not require any base, metal, or other additives.
引用
收藏
页码：1904 / 1914
页数：11
相关论文
共 50 条
  • [21] 1,3-DIPOLAR CYCLOADDITIONS TO ALKYNES - REVIEW
    BASTIDE, J
    HAMELIN, J
    TEXIER, F
    QUANG, YV
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE PARTIE II-CHIMIE MOLECULAIRE ORGANIQUE ET BIOLOGIQUE, 1973, (7-8): : 2555 - 2579
  • [22] Asymmetric 1,3-dipolar cycloadditions of acrylamides
    Kissane, Marie
    Maguire, Anita R.
    CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) : 845 - 883
  • [23] ON MECHANISM OF 1,3-DIPOLAR CYCLOADDITIONS . AREPLY
    HUISGEN, R
    JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (06): : 2291 - &
  • [24] SOME 1,3-DIPOLAR CYCLOADDITIONS TO METHOXYBUTENYNES
    NOEL, M
    VOQUANG, Y
    VOQUANG, L
    COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1970, 270 (01): : 80 - &
  • [25] 1,3-Dipolar cycloadditions of azomethine imines
    Najera, Carmen
    Sansano, Jose M.
    Yus, Miguel
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (32) : 8596 - 8636
  • [26] Stereoselective intramolecular 1,3-dipolar cycloadditions
    Namboothiri, INN
    Hassner, A
    STEREOSELECTIVE HETEROCYCLIC SYNTHESIS III, 2001, 216 : 1 - 49
  • [27] CENTENARY LECTURE - 1,3-DIPOLAR CYCLOADDITIONS
    HUISGEN, R
    PROCEEDINGS OF THE CHEMICAL SOCIETY OF LONDON, 1961, (OCT): : 357 - &
  • [28] Understanding the 1,3-Dipolar Cycloadditions of Allenes
    Yu, Song
    Vermeeren, Pascal
    van Dommelen, Kevin
    Bickelhaupt, F. Matthias
    Hamlin, Trevor A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (50) : 11529 - 11539
  • [29] 1,3-DIPOLAR CYCLOADDITIONS OF FULMINIC ACID
    HUISGEN, R
    CHRISTL, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (05) : 456 - &
  • [30] 1,3-dipolar cycloadditions in aqueous media
    Molteni, Giorgio
    HETEROCYCLES, 2006, 68 (10) : 2177 - +
12345