Indium trichloride (InCl3)catalyzed imino Diels-Alder reactions:: An efficient synthesis of cyclopentaquinolines, azabicyclooctanones and azabicyclononanones.

被引:87
|
作者
Babu, G [1 ]
Perumal, PT [1 ]
机构
[1] Cent Leather Res Inst, Div Organ Chem, Adyar 600020, Chennai, India
关键词
D O I
10.1016/S0040-4020(97)10370-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Anhydrous indium trichloride (InCl3) is found to catalyze the imino Diels-Alder reactions of Schiffs bases with cyclopentadiene, cyclohexen-2-one and cyclohepten-2-one which resulted in facile synthesis of cyclopentaquinolines, azabicyclooctanones and previously unreported series of azabicyclononanones. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1627 / 1638
页数:12
相关论文
共 50 条
  • [21] Imino Diels-Alder reactions catalyzed by oxalic acid dihydrate. Synthesis of tetrahydroquinoline derivatives
    Nagarajan, R
    Perumal, PT
    SYNTHETIC COMMUNICATIONS, 2001, 31 (11) : 1733 - 1736
  • [22] Imino Diels-Alder reactions: One-pot synthesis of tetrahydroquinolines
    Kamble, Vinod T.
    Davane, Bhaskar S.
    Chavan, Sanjay A.
    Muley, Dnyanoba B.
    Atkore, Sandeep T.
    CHINESE CHEMICAL LETTERS, 2010, 21 (03) : 265 - 268
  • [23] Imino Diels-Alder reactions:One-pot synthesis of tetrahydroquinolines
    Vinod T.Kamble
    Bhaskar S.Davane
    Sanjay A.Chavan
    Dnyanoba B.Muley
    Sandeep T.Atkore
    ChineseChemicalLetters, 2010, 21 (03) : 265 - 268
  • [24] Intramolecular Aza-Diels-Alder Cyclization of a Dimerized Citral with Anilines Catalyzed by InCl3
    Chen, Yijang
    Ramanathan, Mani
    Liu, Shiuh-Tzung
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2015, 62 (09) : 761 - 765
  • [25] Imino Diels-Alder/transition metal catalyzed reactions to synthesise fused ring heterocycles
    Taylor, Connor J.
    Alter, Alexander
    Pask, Christopher M.
    Sridharan, Visuvanathar
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2020, 913
  • [26] One pot imino Diels-Alder reaction for the synthesis of 3-aryl-3,4-dihydrobenzo[f]quinoline derivatives catalyzed by antimony trichloride
    Maiti, Gourhari
    Karmakar, Rajiv
    Kayal, Utpal
    TETRAHEDRON LETTERS, 2013, 54 (23) : 2920 - 2923
  • [27] Chiral shift reagent catalyzed, diastereoselective imino Diels-Alder reaction - Synthesis of pyrazolyltetrahydroquinolines
    Sridhar, R
    Perumal, PT
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2006, 84 (03): : 464 - 468
  • [28] HIGH DEGREE OF EXO SELECTIVITY IN IMINO DIELS-ALDER REACTIONS CATALYZED BY TERT-BUTYLDIMETHYLSILYLTRIFLATE
    NOGUE, D
    PAUGAM, R
    WARTSKI, L
    TETRAHEDRON LETTERS, 1992, 33 (10) : 1265 - 1268
  • [29] LANTHANIDE TRIFLATE CATALYZED IMINO DIELS-ALDER REACTIONS - CONVENIENT SYNTHESES OF PYRIDINE AND QUINOLINE DERIVATIVES
    KOBAYASHI, S
    ISHITANI, H
    NAGAYAMA, S
    SYNTHESIS-STUTTGART, 1995, (09): : 1195 - &
  • [30] Indium Trichloride (InCl3) Catalyzed Synthesis of Fused 7-Azaindole Derivatives Using Domino Knoevenagel-Michael Reaction
    Dongare, Sakharam B.
    Chavan, Hemant V.
    Surwase, Datta N.
    Bhale, Pravin S.
    Mule, Yoginath B.
    Bandgar, Babasaheb P.
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2016, 63 (04) : 323 - 330