FeCl3-NaI mediated reactions of aryl azides with 3,4-dihydro-2H-pyran:: a convenient synthesis of pyranoquinolines

被引：37
|
作者：
Kamal, A [1 ]
Prasad, BR [1 ]
Ramana, AV [1 ]
Babu, AH [1 ]
Reddy, KS [1 ]
机构：
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 17期
关键词：
aryl azide; pyranoquinolines; ferric chloride; sodium iodide; reductive cyclization;
D O I：
10.1016/j.tetlet.2004.02.146
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The tetrahydroquinoline moiety is an important structural component of a number of natural products. The reaction of aryl azides with 3,4-dihydro-2H-pyran in the presence of FeCl3-NaI affords the corresponding tetrahydroquinoline derivatives in an efficient manner. Most of the cyclizations exhibited cis selectivity. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3507 / 3509
页数：3
相关论文
共 50 条
  • [31] Directly linked C-disaccharides: Structures of two 3,4-dihydro-2H-pyran derivatives
    Ianelli, S
    Nardelli, M
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 : 2853 - 2857
  • [32] THE THERMAL UNIMOLECULAR DECOMPOSITION OF 3,4-DIHYDRO-2H-PYRAN BEHIND REFLECTED SHOCK-WAVES
    SAITO, K
    ADACHI, K
    WATANABE, M
    SHIMOFUJI, K
    IMAMURA, A
    CHEMICAL PHYSICS LETTERS, 1990, 165 (05) : 383 - 385
  • [33] Control of reactivity of novolac resins:: the use of 3,4-dihydro-2H-pyran as a labile protecting group
    Bateman, SA
    Caulfield, MJ
    Munton, JR
    Solomon, DH
    POLYMER, 2001, 42 (15) : 6339 - 6345
  • [34] NEW SYNTHETIC ROUTES TO SPIROACETALS - THE 3,4-DIHYDRO-2H-PYRAN APPROACH TO (+/-)-TALAROMYCIN-B
    KOCIENSKI, P
    YEATES, C
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (09): : 1879 - 1883
  • [35] SYNTHESIS AND STEREOCHEMICAL CHARACTERIZATION OF OPTICALLY-ACTIVE 2-METHOXY-3,4-DIHYDRO-2H-PYRAN
    MENICAGLI, R
    MALANGA, C
    PECUNIOSO, A
    LARDICCI, L
    GAZZETTA CHIMICA ITALIANA, 1985, 115 (01): : 23 - 27
  • [36] Measurements for the dissociation conditions of methane hydrate in the presence of 2,5-dihydrofuran and 3,4-dihydro-2H-pyran
    Cheng, Chih-Tien
    Chen, Li-Jen
    Lin, Shiang-Tai
    Tang, Muoi
    Chen, Po-Chun
    Chen, Yan-Ping
    FLUID PHASE EQUILIBRIA, 2013, 338 : 114 - 118
  • [37] Unveiling the electron-induced ionization cross sections and fragmentation mechanisms of 3,4-dihydro-2H-pyran
    Wasowicz, Tomasz J.
    Jurkowski, Michal K.
    Harris, Allison L.
    Ljubic, Ivan
    JOURNAL OF CHEMICAL PHYSICS, 2024, 161 (06):
  • [38] On the Nucleophilic Reactions of 5-Trifluoroacetyl-3,4-dihydro-2H-pyranZur nucleophilen Reaktion von 5-Trifluoracetyl-3,4-dihydro-2H-pyran
    Shizheng Zhu
    Guolin Xu
    Chaoyue Qin
    Qianli Chu
    Yong Xu
    Monatshefte für Chemie / Chemical Monthly, 1999, 130 : 671 - 680
  • [39] Specific features of the reaction of 3,4-dihydro-2H-pyran with 2-(chlorosulfanyl)pyridine 1-oxide
    V. K. Osmanov
    G. K. Fukin
    A. V. Borisov
    Russian Chemical Bulletin, 2009, 58 : 650 - 652
  • [40] Specific features of the reaction of 3,4-dihydro-2H-pyran with 2-(chlorosulfanyl)pyridine 1-oxide
    Osmanov, V. K.
    Fukin, G. K.
    Borisov, A. V.
    RUSSIAN CHEMICAL BULLETIN, 2009, 58 (03) : 650 - 652
12345