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
  • [41] NEW METHOD FOR SYNTHESIS OF 2-ACYL-1-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINES
    MOLLOV, NM
    VENKOV, AP
    SYNTHESIS-STUTTGART, 1978, (01): : 62 - 63
  • [42] C1-Functionalization of 1,2,3,4-Tetrahydroisoquinolines (THIQs)
    Tashrifi, Zahra
    Mohammadi Khanaposhtani, Mohammad
    Larijani, Bagher
    Mahdavi, Mohammad
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (10) : 2421 - 2439
  • [43] Preparation of 1,7-disubstituted-1,2,3,4-tetrahydroisoquinolines
    Heer, JP
    Harling, JD
    Thompson, M
    SYNTHETIC COMMUNICATIONS, 2002, 32 (16) : 2555 - 2563
  • [44] Differential roles of 1,2,3,4-tetrahydroisoquinolines in neurodegeneration and neuroprotection
    Antkiewicz-Michaluk, L.
    BEHAVIOURAL PHARMACOLOGY, 2006, 17 (5-6): : 540 - 540
  • [45] SYNTHESIS OF SOME 8-SUBSTITUTED 2-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINES
    REY, M
    VERGNANI, T
    DREIDING, AS
    HELVETICA CHIMICA ACTA, 1985, 68 (07) : 1828 - 1834
  • [46] INTERACTION OF DICHLOROCARBENE WITH SUBSTITUTED 3,4-DIHYDROISOQUINOLINES AND 1-METHYLENE-1,2,3,4-TETRAHYDROISOQUINOLINES
    KHLEBNIKOV, AF
    KOSTIKOV, RR
    SHKLYAEV, VS
    ALEKSANDROV, BB
    DORMIDONTOV, MY
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1990, (08): : 1086 - 1091
  • [47] SYNTHESIS AND STRUCTURE ACTIVITY RELATIONSHIP STUDIES OF A SERIES OF 1,2,3,4-TETRAHYDROISOQUINOLINES SUBSTITUTED IN THE 1-POSITION AND OR 3-POSITION
    MATZ, JR
    DAILEY, MA
    MURRAY, RJ
    RAY, R
    STAGNITTO, M
    PALMER, G
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 204 : 67 - MEDI
  • [48] Synthesis of 1,2,3,4-tetrahydroisoquinolines containing electron-withdrawing groups
    Quallich, GJ
    Makowski, TW
    Sanders, AF
    Urban, FJ
    Vazquez, E
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12): : 4116 - 4119
  • [49] SYNTHESIS OF ISOQUINOLINES .X. 1-ALKYL-1,2,3,4-TETRAHYDROISOQUINOLINES
    BOBBITT, JM
    STEINFEL.AS
    WEISGRAB.KH
    DUTTA, S
    JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (08): : 2478 - &
  • [50] Synthesis of 6,7-dimethoxy-1-halobenzyl-1,2,3,4-tetrahydroisoquinolines
    Cho, SD
    Kweon, DH
    Kang, YJ
    Lee, SG
    Lee, WS
    Yoon, YJ
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (05) : 1151 - 1156