Synthesis of 2-phenyl-4,5,6,7-tetrahydro-1H-indoles with a chiral substituent at the nitrogen atom

被引:0
|
作者
I. A. Andreev
I. O. Ryzhkov
A. V. Kurkin
M. A. Yurovskaya
机构
[1] M. V. Lomonosov State University,
来源
关键词
2-phenyl-4,5,6,7-tetrahydro-1; -indoles; -amino propargylic alcohols; chiral substituent at nitrogen atom; palladium-catalyzed cyclization;
D O I
暂无
中图分类号
学科分类号
摘要
An efficient method has been developed for the enantioselective synthesis of 2-phenyl-4,5,6,7-tetra-hydro-1H-indoles containing chiral substituents at the nitrogen atom. It is based on opening of the epoxide fragment of 1-phenylethynyl-7-oxabicyclo[4.1.0]heptane with chiral amines and/or amino acid esters followed by intramolecular, metal catalyzed cyclization.
引用
收藏
页码:715 / 719
页数:4
相关论文
共 50 条
  • [1] Synthesis of 2-phenyl-4,5,6,7-tetrahydro-1H-indoles with a chiral substituent at the nitrogen atom
    Andreev, I. A.
    Ryzhkov, I. O.
    Kurkin, A. V.
    Yurovskaya, M. A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (05) : 715 - 719
  • [2] New 2-phenyl-4,5,6,7-tetrahydro-2H-indazole derivatives as paddy field herbicides
    Hwang, IT
    Kim, HR
    Jeon, DJ
    Hong, KS
    Song, JH
    Chung, CK
    Cho, KY
    PEST MANAGEMENT SCIENCE, 2005, 61 (05) : 483 - 490
  • [3] Regioselective synthesis of 2-phenyl-4,5,6,7-tetrahydro-2h-pyrazolo[4,3-c]pyridine.
    Shao, H
    Zhang, Q
    Frampton, C
    Vergnon, A
    Goodnow, R
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U583 - U583
  • [4] 2-Aroylcyclohexanones in the synthesis of 4-aryl-5,6,7,8-tetrahydroquinazolines and 3-aryl-4,5,6,7-tetrahydro-1H-indoles
    A. G. Mikhailovskii
    A. A. Pantyukhin
    Russian Journal of Organic Chemistry, 2014, 50 : 1375 - 1376
  • [5] 2-Aroylcyclohexanones in the synthesis of 4-aryl-5,6,7,8-tetrahydroquinazolines and 3-aryl-4,5,6,7-tetrahydro-1H-indoles
    Mikhailovskii, A. G.
    Pantyukhin, A. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (09) : 1375 - 1376
  • [6] Discovery of the 2-phenyl-4,5,6,7-Tetrahydro-1H-indole as a novel anti-hepatitis C virus targeting scaffold
    Andreev, Ivan A.
    Manvar, Dinesh
    Barreca, Maria Letizia
    Belov, Dmitry S.
    Basu, Amartya
    Sweeney, Noreena L.
    Ratmanova, Nina K.
    Lukyanenko, Evgeny R.
    Manfroni, Giuseppe
    Cecchetti, Violetta
    Frick, David N.
    Altieri, Andrea
    Kaushik-Basu, Neerja
    Kurkin, Alexander V.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 96 : 250 - 258
  • [7] Design, synthesis and biological evaluation of novel 2-phenyl-4,5,6,7-tetrahydro-1H-indole derivatives as potential anticancer agents and tubulin polymerization inhibitors
    Wang, Guangcheng
    He, Min
    Liu, Wenjing
    Fan, Meiyan
    Li, Yongjun
    Peng, Zhiyun
    ARABIAN JOURNAL OF CHEMISTRY, 2022, 15 (01)
  • [8] PORPHYRINS WITH EXOCYCLIC RINGS .1. CHEMISTRY OF 4,5,6,7-TETRAHYDRO-1H-INDOLES - SYNTHESIS OF ACETOXY DERIVATIVES, DIHYDROINDOLES, AND NOVEL PORPHYRINS WITH 4 EXOCYCLIC RINGS
    LASH, TD
    BLADEL, KA
    SHINER, CM
    ZAJESKI, DL
    BALASUBRAMANIAM, RP
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (18): : 4809 - 4820
  • [9] 5-Benzyl-1-(4-fluorophenyl)-2-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c] pyridine
    Chopra, D
    Nagarajan, K
    Row, TNG
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O1588 - O1590
  • [10] Oxidative Dearomatization of 4,5,6,7-Tetrahydro-1H-indoles Obtained by Metal- and Solvent-Free Thermal 5-endo-dig Cyclization: The Route to Erythrina and Lycorine Alkaloids
    Andreev, Ivan A.
    Ratmanova, Nina K.
    Novoselov, Anton M.
    Belov, Dmitry S.
    Seregina, Irina F.
    Kurkin, Alexander V.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (21) : 7262 - 7267