Novel, base-promoted reaction of N-alkoxycarbonyl-O-(halosubstituted 4-nitrophenyl)-hydroxylamines

被引:1
|
作者
Boyles, DC [1 ]
Curran, TT [1 ]
Greene, D [1 ]
Macikenas, D [1 ]
Parlett, RV [1 ]
机构
[1] Pfizer Global Res & Dev, Pharmaceut Sci, Ann Arbor, MI 48105 USA
关键词
D O I
10.1016/S0040-4039(02)01536-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper describes base-promoted reactions of N-alkoxycarbonyl-O-(nitrophenyl)hydroxylamines which contain a halogen attached to the aromatic ring. The reaction is promoted under mild conditions (NaHCO3, or K2CO3) and provides the N-alkoxycarbonyl-N-hydroxyaniline. In a crossover experiment, some scrambling was observed which suggests that the reaction is inter- and intramolecular in nature. N-Boc-(2,6-di-Cl-4-NO2-phenyl)hydroxylamine was also found to N-Boc aminate Bn2NH to form the protected hydrazine in modest yield. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6735 / 6737
页数:3
相关论文
共 50 条
  • [1] A NOVEL BASE-PROMOTED N-]O MIGRATION OF A PHOSPHONATE ESTER
    HALL, CR
    INCH, TD
    WILLIAMS, NE
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1983, 18 (1-3): : 441 - 441
  • [2] Chemoselective Amide Formation Using O-(4-Nitrophenyl)hydroxylamines and Pyruvic Acid Derivatives
    Kumar, Sonali
    Sharma, Rashi
    Garcia, Megan
    Kamel, Joseph
    McCarthy, Caroline
    Muth, Aaron
    Phanstiel, Otto
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (23): : 10835 - 10845
  • [3] TRANSITION-STATE STRUCTURES OF BASE-PROMOTED, IMINE-FORMING ELIMINATIONS FROM N-BENZYL-O-(ARYLSULFONYL)HYDROXYLAMINES
    HOFFMAN, RV
    BELFOURE, EL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (08) : 2183 - 2189
  • [4] Synthesis and properties of N-nitro-O-(4-nitrophenyl)hydroxylamine
    Klenov, M. S.
    Churakov, A. M.
    Anikin, O. V.
    Strelenko, Yu. A.
    Tartakovsky, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2009, 58 (10) : 2047 - 2057
  • [5] The formation of aryloxenium ion in the reaction of N-nitro-O-(4-nitrophenyl)hydroxylamine with strong acids
    Klenov, M. S.
    Churakov, A. M.
    Solkan, V. N.
    Strelenko, Yu A.
    Tartakovsky, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2011, 60 (11) : 2263 - 2274
  • [6] The formation of aryloxenium ion in the reaction of N-nitro-O-(4-nitrophenyl)hydroxylamine with strong acids
    M. S. Klenov
    A. M. Churakov
    V. N. Solkan
    Yu. A. Strelenko
    V. A. Tartakovsky
    Russian Chemical Bulletin, 2011, 60 : 2263 - 2274
  • [7] Base-Promoted Ring Expansion Reaction of 4-Quinolones To Access Benzazepinones
    Jiang, Fuhao
    Fan, Rong
    Chen, Bo
    Mu, Tong
    Liu, Xiaofeng
    Xu, Jiasu
    Tan, Xuefei
    Wu, Jun
    ORGANIC LETTERS, 2024, 26 (39) : 8312 - 8316
  • [8] (E)-O-Isopropyl N-(4-nitrophenyl)-thiocarbamate
    Ellis, Carol A.
    Tiekink, Edward R. T.
    Zukerman-Schpector, Julio
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O345 - U5730
  • [9] Synthesis and properties of N-nitro-O-(4-nitrophenyl)hydroxylamine
    M. S. Klenov
    A. M. Churakov
    O. V. Anikin
    Yu. A. Strelenko
    V. A. Tartakovsky
    Russian Chemical Bulletin, 2009, 58 : 2047 - 2057
  • [10] (E)-O-ethyl N-(4-nitrophenyl)thiocarbamate
    Benson, Ronald E.
    Broker, Grant A.
    Daniels, Lee M.
    Tiekink, Edward R. T.
    Wardell, James L.
    Young, David J.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O4106 - O4108