Synthesis of Imidazo[1′,5′:1,2]pyrido[3,4-b]indole Derivatives

被引：0
|
作者：
Magdolna Solymár
Márta Palkó
Tamás Martinek
Ferenc Fülöp
机构：
[1] Institute of Pharmaceutical Chemistry,
[2] University of Szeged,undefined
[3] H-6701 Szeged,undefined
[4] Hungary,undefined
来源：
Monatshefte für Chemie / Chemical Monthly | 2002年 / 133卷
关键词：
Keywords. β-Carbolines; Hydantoins; Thiohydantoins; Keto-enol tautomerism.;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
 The reactions of 1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid and its ethyl ester with alkyl and aryl isothiocyanates under mild conditions resulted in the corresponding thiohydantoin-fused tetrahydro-β-carbolines. Treatment of the ethyl ester with isocyanates furnished ethyl 2-alkyl- or arylcarbamoyl-1,2,3,4-tetrahydro-β-carboline-1-carboxylates which were transformed to hydantoin-fused tetrahydro-β-carbolines. The structures of the thiohydantoin compounds, involving two conformers and the presence of keto-enol tautomerism, were determined by NMR spectroscopy.
引用
下载
收藏
页码：1423 / 1430
页数：7
相关论文
共 50 条
  • [1] Synthesis of imidazo[1′,5′:1,2]pyrido [3,4-b]indole derivatives
    Solymár, M
    Palkó, M
    Martinek, T
    Fülöp, F
    MONATSHEFTE FUR CHEMIE, 2002, 133 (11): : 1423 - 1430
  • [2] Unprecedented base-promoted oxidation of imidazo[1′,5′:1,2]pyrido[3,4-b]indoles
    De la Figuera, N
    Garcia-Lopez, MT
    Herranz, R
    Gonzalez-Muniz, R
    HETEROCYCLES, 1998, 48 (10) : 2061 - 2070
  • [3] UNUSUAL FORMATION OF A NOVEL PYRROLO[1',2'/1,2]PYRIDO[3,4-B]INDOLE
    GIRI, VS
    DAS, SK
    SANKAR, PJ
    SHOOLERY, JN
    KEIFER, P
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (04) : 767 - 769
  • [4] Synthesis of derivatives of a new heterocyclic system pyrazolo[3,4-b]pyrido[1′,2′:1,2]imidazo[4,5-d]pyridine
    Komarova, E. S.
    Makarov, V. A.
    Alekseeva, L. M.
    Avramenko, G. V.
    Granik, V. G.
    RUSSIAN CHEMICAL BULLETIN, 2006, 55 (04) : 735 - 740
  • [5] Synthesis of derivatives of a new heterocyclic system pyrazolo[3,4-b]pyrido[1′,2′: 1,2]imidazo[4,5-d]pyridine
    E. S. Komarova
    V. A. Makarov
    L. M. Alekseeva
    G. V. Avramenko
    V. G. Granik
    Russian Chemical Bulletin, 2006, 55 : 735 - 740
  • [6] Pyrazolo[3,4-b]pyridine in heterocyclic synthesis:: synthesis of new pyrazolo[3,4-b]pyridines, imidazo[1′,2′:1,5]pyrazolo[3,4-b]pyridines, and pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidines
    Gad-Elkareem, Mohamed A. M.
    Abdel-Fattah, Azza M.
    Elneairy, Mohamed A. A.
    CANADIAN JOURNAL OF CHEMISTRY, 2007, 85 (09) : 592 - 599
  • [7] NMR-SPECTROSCOPY OF HEXAHYDROPYRAZINO[1',2'-1,2]PYRIDO[3,4-B]INDOLES AND OCTAHYDROPYRAZINO[1',2'-1,2]PYRIDO[3,4-B]INDOLES AND 15-AZAYOHIMBANES
    VALLS, N
    SEGARRA, VM
    BONJOCH, J
    MAGNETIC RESONANCE IN CHEMISTRY, 1991, 29 (10) : 985 - 992
  • [8] NEW PYRIMIDO[1',6'/1,2]PYRIDO[3,4-B]INDOLES
    DOMANY, G
    SZANTAY, C
    BIHARI, M
    SCHON, I
    SYNTHETIC COMMUNICATIONS, 1993, 23 (13) : 1787 - 1794
  • [9] 1-METHYL-2,3,4,9-TETRAHYDRO-1H-PYRIDO(3,4-B)INDOLE, 1-PHENYL-2,3,4,9-TETRAHYDRO-1H-PYRIDO(3,4-B)INDOLE AND 1-(2-(2-DIMETHYLAMINOETHOXY)-PHENYL)-2,3,4,9-TETRAHYDRO-1H-PYRIDO[3,4-B]INDOLE AND THEIR 2-SUBSTITUTED DERIVATIVES - SYNTHESIS AND PHARMACOLOGICAL SCREENING
    HULINSKA, H
    TAUFMANN, P
    FRYCOVA, H
    PROTIVA, M
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1988, 53 (02) : 373 - 380
  • [10] Thee-component, one-pot synthesis of hexahydroazepino [3,4-b]indole and tetrahydro-1H-pyrido[3,4-b]indole derivatives and evaluation of their cytotoxicity
    Reddy, B. V. Subba
    Ganesh, A. Venkata
    Vani, M.
    Murthy, T. Ramalinga
    Kalivendi, Shasi V.
    Yadav, J. S.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (18) : 4501 - 4503
12345