New synthesis of ethambutol and related α,β-acetylenic amino alcohols

被引:3
|
作者
Mavrov, M. V. [1 ]
Simirskaya, N. I. [1 ]
机构
[1] Russian Acad Sci, Zelinskii Inst Organ Chem, Moscow, Russia
关键词
ethambutol; alpha-bromoallenic alcohol; vicinal amino alcohols; N-derivatives of hydroxyamino-alkynes; allenyl substitution; enantiomeric separation; ANTITUBERCULOUS AGENTS; (S; S)-ETHAMBUTOL;
D O I
10.1007/s11094-013-0880-y
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Ethambutol was obtained in 35% overall yield in three steps by enantiomeric separation of rac-2-benzylamino-3-butyl-1-ol, alkylation of the S-enantiomer with 1,2-dibromoethane, and catalytic N-debenzylation.
引用
收藏
页码:730 / 735
页数:6
相关论文
共 50 条
  • [1] New synthesis of ethambutol and related α,β-acetylenic amino alcohols
    M. V. Mavrov
    N. I. Simirskaya
    Pharmaceutical Chemistry Journal, 2013, 46 : 730 - 735
  • [2] Mannich synthesis of acetylenic amino alcohols in aqueous ionic liquids
    Simirskaya, Nina I.
    Ignat'ev, Nikolai V.
    Schulte, Michael
    Zlotin, Sergei G.
    MENDELEEV COMMUNICATIONS, 2012, 22 (06) : 317 - 319
  • [3] Stereoselective synthesis of enantioenriched acetylenic 1,2-amino alcohols
    Chemla, Fabrice
    Ferreira, Franck
    Gaucher, Xavier
    Palais, Laetitia
    SYNTHESIS-STUTTGART, 2007, (08): : 1235 - 1241
  • [4] SYNTHESIS OF HIGHER ACETYLENIC ALCOHOLS
    KOVALEV, BG
    MATVEEVA, ED
    STAN, VV
    VOVK, GA
    YUDIN, LG
    KOST, AN
    ZHURNAL ORGANICHESKOI KHIMII, 1980, 16 (10): : 2032 - 2038
  • [5] Synthesis of acetylenic alcohols.
    Yang, KC
    Upasani, RB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U1184 - U1184
  • [6] SYNTHESIS OF DI(2-CHLOROETHYL) AMINO DERIVATIVES OF TERTIARY ACETYLENIC ALCOHOLS AND ETHERS
    AZERBAEV, IN
    POPLAVSK.IA
    KONDAURO.GN
    CHERMANO.GB
    ZHURNAL ORGANICHESKOI KHIMII, 1973, 9 (02): : 252 - 255
  • [7] GENERAL METHOD FOR SYNTHESIS OF ALPHA-AMINO-BETA,GAMMA-ACETYLENIC ALCOHOLS
    EPSZTEIN, R
    MERCIER, F
    SYNTHESIS-STUTTGART, 1977, (03): : 183 - 184
  • [8] Synthesis of Peroxy-Containing Acetylenic Alcohols and Ethers Derived from γ-Amino Ketones
    E. A. Dikusar
    N. G. Kozlov
    L. A. Popova
    K. L. Moiseichuk
    A. P. Yuvchenko
    Russian Journal of General Chemistry, 2003, 73 : 591 - 595
  • [9] SYNTHESIS AND MICROBIOLOGICAL EVALUATION OF ACETYLENIC AMINO ALCOHOLS N-PHENYL CARBAMATE DERIVATIVES
    Kassymova, M. K.
    Nauryzbayev, M. K.
    Mamyrbekova, A. K.
    Mamitova, A. D.
    Mamyrbekova
    Chechina, O. N.
    NEWS OF THE NATIONAL ACADEMY OF SCIENCES OF THE REPUBLIC OF KAZAKHSTAN-SERIES CHEMISTRY AND TECHNOLOGY, 2019, (04): : 43 - 48
  • [10] Synthesis of peroxy-containing acetylenic alcohols and ethers derived from γ-amino ketones
    Dikusar, EA
    Kozlov, NG
    Popova, LA
    Moiseichuk, KL
    Yuvchenko, AP
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2003, 73 (04) : 591 - 595