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
  • [1] Diastereoselective synthesis of 2-isoxazolines via silaketal tethered 1,3-dipolar cycloadditions
    Marrugo, H
    Dogbéavou, R
    Breau, L
    TETRAHEDRON LETTERS, 1999, 40 (51) : 8979 - 8983
  • [2] Synthesis of isoxazolines by 1,3-dipolar cycloaddition and their bioactivity
    Cheng, CS
    Li, ZN
    Su, JY
    Li, T
    Zhang, BY
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (11) : 1392 - 1397
  • [3] Enantioselective Synthesis of 4-Isoxazolines by 1,3-Dipolar Cycloadditions of Nitrones to Alkynals Catalyzed by Fluorodiphenylmethylpyrrolidines
    Aleman, Jose
    Fraile, Alberto
    Marzo, Leyre
    Ruano, Jose Luis Garcia
    Izquierdo, Cristina
    Diaz-Tendero, Sergio
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (09) : 1665 - 1671
  • [4] 1,3-DIPOLAR CYCLOADDITIONS OF HETEROCYCLES .22. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF CONDENSED ISOXAZOLINES
    KONOPIKOVA, M
    FISERA, L
    STURDIK, E
    UJHELYOVA, R
    VARKONDA, S
    HYBLOVA, O
    CHEMICAL PAPERS, 1991, 45 (06): : 775 - 787
  • [5] 1,3-DIPOLAR CYCLOADDITIONS TO BICYCLIC OLEFINS .1. 1,3-DIPOLAR CYCLOADDITIONS TO NORBORNADIENES
    TANIGUCHI, H
    IKEDA, T
    YOSHIDA, Y
    IMOTO, E
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (10) : 2694 - 2699
  • [6] 1,3-Dipolar Cycloadditions of β-Fluoroalkyl Vinylsulfones and Nitrile Oxides for Fluoroalkylated Isoxazolines and Isoxazoles
    Ou, Zhi
    Huang, Qian
    Kou, Ying-Da
    Cheng, Feng
    Kalita, Subarna Jyoti
    Zhao, Zhen-Ni
    Huang, Yi-Yong
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (12) : 2184 - 2187
  • [7] ON MECHANISM OF 1,3-DIPOLAR CYCLOADDITIONS
    FIRESTONE, RA
    JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (06): : 2285 - +
  • [8] Natural 1,3-Dipolar Cycloadditions
    Baunach, Martin
    Hertweck, Christian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (43) : 12550 - 12552
  • [9] 1,3-DIPOLAR CYCLOADDITIONS TO OXIDOPYRAZINIUMS
    KISS, M
    RUSSELLMAYNARD, J
    JOULE, JA
    TETRAHEDRON LETTERS, 1987, 28 (19) : 2187 - 2190
  • [10] Studies on 1,3-dipolar cycloadditions
    Banerji, A
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2000, 77 (11-12) : 637 - 649
12345