Synthesis of CF3-substituted 1,2,3,4-tetrahydroisoquinolines and 1,2,3,6-tetrahydropyridines

被引：0
|
作者：
I. Yu. Chernyshov
V. V. Levin
A. D. Dilman
P. A. Belyakov
M. I. Struchkova
V. A. Tartakovsky
机构：
[1] Russian Academy of Sciences,N. D. Zelinsky Institute of Organic Chemistry
来源：
Russian Chemical Bulletin | 2010年 / 59卷
关键词：
trifluoromethylation; amines; trimethyl(trifluoromethyl)silane;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A three-step method for the preparation of CF3-substituted 1,2,3,4-tetrahydroisoquino-lines and 1,2,3,6-tetrahydropyridines has been suggested. The first step includes alkylation of isoquinoline or 4-methylpyridine at the nitrogen atom with the formation of salts, which are involved into the reaction with Grignard reagent or lithium triethylborohydride to give enamines. The enamines undergo nucleophilic trifluoromethylation upon the action of Me3SiCF3 under acidic conditions.
引用
收藏
页码：2102 / 2107
页数：5
相关论文
共 50 条
  • [1] Synthesis of CF3-substituted 1,2,3,4-tetrahydroisoquinolines and 1,2,3,6-tetrahydropyridines
    Chernyshov, I. Yu.
    Levin, V. V.
    Dilman, A. D.
    Belyakov, P. A.
    Struchkova, M. I.
    Tartakovsky, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2010, 59 (11) : 2102 - 2107
  • [2] SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLINES
    KASHDAN, DS
    SCHWARTZ, JA
    RAPOPORT, H
    JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13): : 2638 - 2643
  • [3] Synthesis of substituted 1,2,3,4-tetrahydroisoquinolines as anticancer agents
    Redda, Kinfe Ken
    Gangapuram, Madhavi N. A.
    Ardley, Tiffany W.
    CANCER RESEARCH, 2010, 70
  • [4] SYNTHESIS OF SUBSTITUTED 1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES
    VOMERO, S
    CHIMENTI, F
    FARMACO-EDIZIONE SCIENTIFICA, 1976, 31 (02): : 98 - 104
  • [5] Synthesis and Contractile Activity of Substituted 1,2,3,4-Tetrahydroisoquinolines
    Ivanov, Iliyan
    Nikolova, Stoyanka
    Aladjov, Dimo
    Stefanova, Iliyana
    Zagorchev, Plamen
    MOLECULES, 2011, 16 (08): : 7019 - 7042
  • [6] Stereoselective synthesis of substituted isochromans and 1,2,3,4-tetrahydroisoquinolines
    Chen, Zhilong
    Sun, Jianwei
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [7] Expedient synthesis of 3-substituted-1,2,3,6-tetrahydropyridines
    Alcaraz, Lilian
    de Neuville, Bertrand Coquebert
    Lister, Andrew
    Roberts, Bryan
    TETRAHEDRON LETTERS, 2011, 52 (45) : 5940 - 5942
  • [8] A NEW SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLINES
    BOBBITT, JM
    KHANNA, KL
    KIELY, JM
    CHEMISTRY & INDUSTRY, 1964, (47) : 1950 - 1951
  • [9] SYNTHESIS OF DEUTERATED 1,2,3,4-TETRAHYDROISOQUINOLINES
    MEESE, CO
    EBNER, T
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1988, 25 (03): : 335 - 343
  • [10] SUBSTITUTED 1-CYANO-1,2,3,4-TETRAHYDROISOQUINOLINES
    BOHME, H
    SCHWEITZ.R
    ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESSELSCHAFT, 1970, 303 (03): : 225 - &
12345