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
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 32 条
  • [1] [Anonymous], [No title captured], Patent No. [WO 0127086, 0127086]
  • [2] Convenient synthesis of pyrano[3,2-c]quinolines and indeno[2,1-c] quinolines by imino Diels-Alder reactions
    Babu, G
    Perumal, PT
    [J]. TETRAHEDRON LETTERS, 1998, 39 (20) : 3225 - 3228
  • [3] Biller S. A., 1989, U.S. Patent, Patent No. [4843,082, 4843082, 4,843,082]
  • [4] Boger D.L., 1987, HETERO DIELS ALDER M
  • [5] ANTICONVULSANT ACTIVITY OF GLYCINE-SITE NMDA ANTAGONISTS .2. TRANS 2-CARBOXY-4-SUBSTITUTED TETRAHYDROQUINOLINES
    CARLING, RW
    LEESON, PD
    MOSELEY, AM
    SMITH, JD
    SAYWELL, K
    TRICKLEBANK, MD
    KEMP, JA
    MARSHALL, GR
    FOSTER, AC
    GRIMWOOD, S
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (01) : 65 - 70
  • [6] CELING RW, 1992, J MED CHEM, V35, P1942
  • [7] Synthesis of 2-CF3-tetrahydroquinoline and quinoline derivatives from CF3-N-aryl-aldimine
    Crousse, B
    Bégué, JP
    Bonnet-Delpon, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) : 5009 - 5013
  • [8] Cuny G. D., 1999, PCT Int. Appl., Patent No. [WO 9967238, 9967238]
  • [9] JIANHENG Z, 2002, J ORG CHEM, V67, P3969
  • [10] 2,4-DIAMINO-5-BENZYLPYRIMIDINES AND ANALOGS AS ANTIBACTERIAL AGENTS .12. 1,2-DIHYDROQUINOLYLMETHYL ANALOGS WITH HIGH-ACTIVITY AND SPECIFICITY FOR BACTERIAL DIHYDROFOLATE-REDUCTASE
    JOHNSON, JV
    RAUCKMAN, BS
    BACCANARI, DP
    ROTH, B
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (08) : 1942 - 1949