A practical and mild chlorination of fused heterocyclic N-oxides

被引:34
|
作者
Wang, Dong [1 ]
Jia, Hailing [2 ]
Wang, Wuchang [2 ]
Wang, Zhe [1 ]
机构
[1] Longwood Biopharmaceut Co Ltd, Tianjin Int Joint Acad Biomed, Tianjin 300457, Peoples R China
[2] Nankai Univ, Sch Med, Tianjin 300071, Peoples R China
关键词
Chlorination; N-Oxides; Vilsmeier reagent; Quinoline; Isoquinoline; INHIBITORS; QUINOLINES; CONVERSION;
D O I
10.1016/j.tetlet.2014.11.005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Fused azine N-oxides were selectively chlorinated at C2 in moderate to excellent yields, employing Vilsmeier reagent as both the activating agent and the nucleophilic chloride source. Remarkable features of the method include simple operation, mild reaction conditions, a wide substrate scope, and the use of only stoichiometric amount of POCl3. The potential extension of this method to a one-pot oxidation/chlorination sequence that obviates the need for isolation of the N-oxide intermediates is also validated. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7130 / 7132
页数:3
相关论文
共 50 条
  • [21] Mild and efficient reduction of amine N-oxides
    Kokatla, Hari P.
    Thomson, Paul F.
    Bae, Suyeal
    Lakshman, Mahesh K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [22] Deoxygenation of N-heterocyclic N-oxides with Selectfluor and disulfane
    Celikoglu, Muhammed Hanifi
    Ucar, Sefa
    Nisanci, Bilal
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 61 (07) : 1029 - 1034
  • [23] Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents
    An, Ju Hyeon
    Kim, Kyu Dong
    Lee, Jun Hee
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (03): : 2876 - 2894
  • [24] Heterocyclic N-Oxides - An Emerging Class of Therapeutic Agents
    Mfuh, A. M.
    Larionov, O. V.
    CURRENT MEDICINAL CHEMISTRY, 2015, 22 (24) : 2819 - 2857
  • [25] DEOXYGENATION OF HETEROCYCLIC N-OXIDES BY CHROMIUM(II) CHLORIDE
    AKITA, Y
    MISU, K
    WATANABE, T
    OHTA, A
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1976, 24 (08) : 1839 - 1841
  • [26] AN IMPROVED PROCEDURE FOR THE PREPARATION OF AROMATIC HETEROCYCLIC N-OXIDES
    RHIE, SY
    RYU, EK
    HETEROCYCLES, 1995, 41 (02) : 323 - 328
  • [27] NATURAL ABUNDANCE O-17 NMR-SPECTROSCOPY OF HETEROCYCLIC N-OXIDES AND DI N-OXIDES
    BALAKRISHNAN, P
    BAUMSTARK, AL
    BOYKIN, DW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 189 (APR-): : 135 - ORGN
  • [28] IMIDAZOLE N-OXIDES AND BENZIMIDAZOLE N-OXIDES
    LETTAU, H
    ZEITSCHRIFT FUR CHEMIE, 1970, 10 (06): : 211 - &
  • [29] Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN
    Qiao, Kai
    Wan, Li
    Sun, Xiaoning
    Zhang, Kai
    Zhu, Ning
    Li, Xin
    Guo, Kai
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (08) : 1606 - 1611
  • [30] MEDIUM AND SUBSTITUENT EFFECTS ON THE PHOTOCHEMISTRY OF PHENANTHRIDINE N-OXIDES - IS AN INTERMEDIATE OF DIRADICAL CHARACTER INVOLVED IN THE PHOTOREARRANGEMENT OF HETEROCYCLIC N-OXIDES
    ALBINI, A
    FASANI, E
    FRATTINI, V
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1988, (02): : 235 - 240