SYNTHESIS OF 4-ARYL-5,6-DIHYDRO-BENZO[H]QUINOLINES - HETEROCYCLES BY MICHAEL REACTIONS, .2.

被引:28
作者
OTTO, HH [1 ]
RINUS, O [1 ]
SCHMELZ, H [1 ]
机构
[1] UNIV MARBURG,INST PHARMAZEUT CHEM,D-3550 MARBURG 1,FED REP GER
来源
MONATSHEFTE FUR CHEMIE | 1979年 / 110卷 / 01期
关键词
Benzo[h]quinolines; Mechanism; Michael addition;
D O I
10.1007/BF00903753
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new route to the benzo[h]quinoline system 3 by Michael-addition of malononitrile to 2-arylidene-1-tetralones 1 is presented. The mechanism of this reaction is elucidated by isolation of the intermediate 4H-naphtho[1,2-b]-pyrane 2 and its reaction to 3. The reaction is proposed to be a sequence of addition, cyclisation, Dimroth-rearrangement and disproportionation. © 1979 Springer-Verlag.
引用
收藏
页码:115 / 119
页数:5
相关论文
共 11 条
  • [1] [Anonymous], 1959, ORGANIC REACT
  • [2] BARAT C, 1931, J INDIAN CHEM SOC, V8, P699
  • [3] HOUSE HO, 1972, MODERN SYNTHETIC REA, P595
  • [4] Delta ketonic nitriles and their relation to cyclic compounds II
    Kohler, EP
    Souther, BL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1922, 44 : 2903 - 2914
  • [5] KRAUCH H, 1976, REAKTIONEN ORGANISCH
  • [6] Michael A., 1887, J PRAKT CHEM, V35, P349
  • [7] SYNTHESIS OF SOME 4H-PYRANO[2.3-C]PYRAZOLES
    OTTO, HH
    [J]. ARCHIV DER PHARMAZIE, 1974, 307 (06) : 444 - 447
  • [8] RAFFAUF RF, 1970, HDB ALKALOIDS
  • [9] The production of polycycic aromatic types through the cycloDehydration of unsaturated ketones
    Rapson, WS
    Shuttleworth, RG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1940, : 636 - 641
  • [10] SCHMELZ H, 1978, THESIS MARBURG