An efficient method for the synthesis of benzo[f]quinoline and benzo[a]phenanthridine derivatives catalyzed by iodine by a three-component reaction of arenecarbaldehyde, naphthalen-2-amine, and cyclic ketone

被引：74
作者：
Wang, Xiang-Shan [1 ,2 ]
Li, Qing [1 ]
Yao, Chang-Sheng [1 ]
Tu, Shu-Jiang [1 ,2 ]
机构：
[1] Xuzhou Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Jiangsu, Peoples R China
[2] Key Lab Biotechnol Med Plants, Xuzhou 221116, Jiangsu, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 20期
关键词：
benzo[f]quinoline; benzo[a]phenanthridine; iodine; cycloketone; multicomponent reactions; heterocycles;
D O I：
10.1002/ejoc.200800287
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild, efficient, and general method for the synthesis of benzo[f]quinoline and benzo[a]phenanthridine derivatives by a three-component reaction of arenecarbaldehyde, naphthalen-2-amine, and cyclic ketone using iodine as catalyst is described. A possible reaction mechanism for the formation of the product is proposed based on further experimental results. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
引用
收藏
页码：3513 / 3518
页数：6
相关论文
共 87 条
  • [1] PREPARATIVE CHIRAL HPLC SEPARATION OF ALL POSSIBLE STEREOISOMERS OF LY191704 AND LY266111 AND THEIR IN-VITRO INHIBITION OF HUMAN TYPE-1 AND TYPE-2 STEROID 5-ALPHA-REDUCTASES
    ABELL, AD
    ERHARD, KF
    YEN, HK
    YAMASHITA, DS
    BRANDT, M
    MOHAMMED, H
    LEVY, MA
    HOLT, DA
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (11) : 1365 - 1368
  • [2] Albert P., 2006, TETRAHEDRON, V63, P5341
  • [3] Iodine-catalysed Bohlmann-Rahtz cyclodehydration reactions
    Bagley, MC
    Glover, C
    Chevis, D
    [J]. SYNLETT, 2005, (04) : 649 - 651
  • [4] BAHUGUNA R P, 1988, Egyptian Journal of Chemistry, V31, P89
  • [5] BAHUGUNA RP, 1992, J INDIAN CHEM SOC, V69, P401
  • [6] BAHUGUNA RP, 1994, INDIAN J HETEROCY CH, V3, P265
  • [7] Bandgar BP, 2004, J CHEM RES-S, P389
  • [8] Molecular iodine catalyzed highly rapid synthesis of 1,5-benzodiazepine derivatives under mild conditions
    Bandgar, BP
    Bettigeri, SV
    Joshi, NS
    [J]. SYNTHETIC COMMUNICATIONS, 2004, 34 (08) : 1447 - 1453
  • [9] Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions
    Bandgar, BP
    Shaikh, KA
    [J]. TETRAHEDRON LETTERS, 2003, 44 (09) : 1959 - 1961
  • [10] A remarkable iodine-catalyzed protection of carbonyl compounds
    Banik, BK
    Chapa, M
    Marquez, J
    Cardona, M
    [J]. TETRAHEDRON LETTERS, 2005, 46 (13) : 2341 - 2343
123456789