Annelation of lactam rings to 2,3,4,4a-tetrahydro-1H-carbazole derivatives

被引:0
|
作者
Sackus, A [1 ]
Krikstolaityte, S [1 ]
Martynaitis, V [1 ]
机构
[1] Kaunas Univ Technol, Dept Organ Chem, LT-3028 Kaunas, Lithuania
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the reaction of 4a-methyl-2,3,4,4a-tetrahydro-1H-carbazole and its 6-methyl- and 6-bromosubslituted derivatives with 2-chloroacetamide respective 9-carbamoylmethyl-4a-methyl-2,3,4,4a-tetrahydro- 1H-carbazolium chlorides are formed, which can be cyclized into 5,6,7,7a-tetrahydro-1H,4H-imidazo[2, 1-k] carbazol-2(3H)-one derivatives. Reaction of 4a methyl-2,3,4, 4a-tetrahydro-1H-carbazole hydrochloride with acrylamide gives 4a-methyl-1,2,6,7,8,8a-hexahydro-5H-pyrimido [2,1-k]carbazol-3 (4H)-one. 7a,12-Dimethyl-3,4,4a,5,6,7,7a,12-octahydropyrido [3,2-j]carbazol-2(1H)-one was synthesized by the reaction of 4a,9-dimethyl-2,3,4,4a-tetrahydro-9H-carbazole with acrylamide.
引用
收藏
页码:645 / 648
页数:4
相关论文
共 50 条
  • [31] N-Methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamidesas a novel class of cannabinoid receptors agonists with low CNS penetration
    Wei, Zhongyong
    Yang, Hua
    Liu, Ziping
    Tremblay, Maxime
    Johnstone, Shawn
    Beha, Sara
    Yue, Shi Yi
    Srivastava, Sanjay
    Tomaszewski, Miroslaw J.
    Brown, William
    Walpole, Christopher
    St-Onge, Stephane
    Lessard, Etienne
    Archambault, Anne-Julie
    Groblewski, Thierry
    Page, Daniel
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (12) : 3884 - 3889
  • [32] A NEW SYNTHETIC METHOD FOR PREPARATION OF 1,3,4,5-TETRAHYDRO-2H-1-BENZAZEPIN-2-ONE DERIVATIVES
    ITO, Y
    KOBAYASHI, K
    MAENO, M
    SAEGUSA, T
    CHEMISTRY LETTERS, 1980, (05) : 487 - 490
  • [33] 1,2,3,4-TETRAHYDROCARBAZOLE - CARBAZOLE, 1,2,3,4-TETRAHYDRO
    ROGERS, CU
    CORSON, BB
    ORGANIC SYNTHESES, 1950, 30 : 90 - 92
  • [34] Stereochemical studies of the isomerization of novel 2-alkyl-9-phenyl-2,3,4,4a- and 2,3,4,9-tetrahydro-1H-indeno[2,1-c]pyridines
    Upton, C
    Jaffar, M
    JOURNAL OF PHARMACY AND PHARMACOLOGY, 1998, 50 (08) : 829 - 835
  • [35] MASS-SPECTRA OF NEW "3,5-METHANO-2,3,4,5-TETRAHYDRO-1H-1 AND "3,5-METHANO-2,3,4,5-TETRAHYDRO-1H-2 BENZAZEPINES AND OXO DERIVATIVES
    ESCALE, R
    ELKHAYAT, A
    VIDAL, JP
    GIRARD, JP
    ROSSI, JC
    ORGANIC MASS SPECTROMETRY, 1986, 21 (06): : 379 - 380
  • [36] Synthesis of 9-substituted 2,3,4,9-tetrahydro-1H-carbazole derivatives and evaluation of their anti-prion activity in TSE-infected cells
    Kimura, Tsutomu
    Hosokawa-Muto, Junji
    Asami, Kenji
    Murai, Toshiaki
    Kuwata, Kazuo
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (11) : 5675 - 5679
  • [37] Synthesis and molecular structure of 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives and dimethyl 4-cyano-2,3,6,7-tetrahydro-1H-3-benzazonine-5,6-dicarboxylate
    Soldatenkov, A. T.
    Soldatova, S. A.
    Mamyrbekova-Bekro, J. A.
    Gimranova, G. S.
    Malkova, A. V.
    Polyanskii, K. B.
    Kolyadina, N. M.
    Khrustalev, V. N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (09) : 1332 - 1339
  • [38] Synthesis and molecular structure of 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives and dimethyl 4-cyano-2,3,6,7-tetrahydro-1H-3-benzazonine-5,6-dicarboxylate
    A. T. Soldatenkov
    S. A. Soldatova
    J. A. Mamyrbekova-Bekro
    G. S. Gimranova
    A. V. Malkova
    K. B. Polyanskii
    N. M. Kolyadina
    V. N. Khrustalev
    Chemistry of Heterocyclic Compounds, 2012, 48 : 1332 - 1339
  • [39] Synthesis of 2,3-diaryl-2,3,4,4a-tetrahydro-5H-indeno[1,2-c]pyridazin-5-ones
    Chagarovskiy, Alexey O.
    Strel'tsova, Elena D.
    Rybakov, Victor B.
    Levina, Irina I.
    Trushkov, Igor V.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (03) : 240 - 245
  • [40] Synthesis of novel 1-substituted and 1,9-disubstituted-1,2,3,4-tetrahydro-9H-carbazole derivatives as potential anticancer agents
    Shmeiss, NAMM
    Ismail, MMF
    Soliman, AM
    El-Diwani, HI
    MOLECULES, 2000, 5 (10) : 1101 - 1112