Synthesis of phenanthridones using Diels-Alder reactions of 4-substituted 2(1H)-quinolones acting as dienophiles

被引:14
作者
Fujita, R
Watanabe, K
Yoshisuji, T
Matsuzaki, H
Harigaya, Y
Hongo, H
机构
[1] Tohoku Pharmaceut Univ, Aoba Ku, Sendai, Miyagi 9818558, Japan
[2] Kitasato Univ, Sch Pharmaceut Sci, Minato Ku, Tokyo 1088642, Japan
关键词
4-substituted 2(1H)-quinolone; Diels-Alder reaction; phenanthridone; MO calculation; high pressure; electron-withdrawing group;
D O I
10.1248/cpb.49.407
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Diels-Alder reactions of 2(1H)-quinolones having an electron-withdrawing group at the 4-position with 1,3-butadiene derivatives were carried out to give the phenanthridones richly functionalized under the conditions of atmospheric and high pressure. Furthermore, the reactivities of 4-substituted 2(1H)-quinolones acting as a dienophile were examined using MO calculation.
引用
收藏
页码:407 / 412
页数:6
相关论文
共 30 条
[1]   REACTIONS OF DIHYDROQUINOLINES AND DIHYDROISOQUINOLINES WITH ARENESULFONYL AZIDES [J].
BAILEY, AS ;
MORRIS, T ;
RASHID, Z .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (05) :420-424
[2]   NARCICLASINE - AN ANTIMITOTIC SUBSTANCE FROM NARCISSUS BULBS [J].
CERIOTTI, G .
NATURE, 1967, 213 (5076) :595-&
[3]   BROMINATION STUDIES OF ALKYL-SUBSTITUTED 2-PYRIDONES AND 2-QUINOLONES [J].
COOK, DJ ;
SORTER, P ;
DANIELS, E ;
BOWEN, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (12) :4949-&
[4]   1-METHYL-4-CARBOSTYRILCARBOXALDEHYDE AND CERTAIN CONDENSATION PRODUCTS [J].
COOK, DJ ;
STAMPER, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (06) :1467-1468
[5]   NYBOMYCIN .7. PREPARATIVE ROUTES TO NYBOMYCIN AND DEOXYNYBOMYCIN [J].
FORBIS, RM ;
RINEHART, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) :5003-5013
[6]  
Frisch M.J., 2016, Gaussian 16 Revision C. 01. 2016, V16, P01
[7]  
Fujita R, 2000, CHEM PHARM BULL, V48, P1814
[8]  
FUJITA R, 1992, ANN REPORT TOHOKU CO, V39, P91
[9]  
FUJITA R, 1999, J TOHOKU PHARM U, V46, P77
[10]  
FUJITA R, 1997, J CHEM SOC P1, V44, P105