Novel Diels-Alder reaction of 4-nitro-1(2H)-isoquinolones

被引:8
作者
Fujita, R [1 ]
Wakayanagi, S [1 ]
Wakamatsu, H [1 ]
Matsuzaki, H [1 ]
机构
[1] Tohoku Pharmaceut Univ, Aoba Ku, Sendai, Miyagi 9818558, Japan
关键词
4-nitro-1(2H)-isoquinolone; 5(6H)-phenanthridone; Diels-Alder reaction; inhibitor; regioselectivity; calculation;
D O I
10.1248/cpb.54.209
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A novel Diels-Alder (DA) reaction with 4-nitro-1(2H)-isoquinolones acting as the dienophile afforded 5(6H)-phenanthridone derivatives. The DA reaction of 4-nitro-1(2H)-isoquinolone with 1-methoxy-1,3-butadiene gave biologically active 5(6H)-phenanthridone possessing in a high yield. Regioselectivity of 4-nitro-1(2H)-isoquinolones with 1-methoxy-3-silyloxy-1,3-butadiene was calculated using molecular orbital (MO) calculations.
引用
收藏
页码:209 / 212
页数:4
相关论文
共 14 条
[1]   SOME DIELS-ALDER REACTIONS WITH 4-VINYL ISOQUINOLINE DERIVATIVES [J].
DYKE, SF ;
SAINSBUR.M ;
BROWN, DW ;
CLIPPERT.RD .
TETRAHEDRON, 1970, 26 (24) :5969-&
[2]  
Frisch M.J., 2004, Gaussian 03
[3]  
Revision C.02
[4]   Aryl-aryl coupling reaction using a novel and highly active palladium reagent prepared from Pd(OAc)2, 1,3-bis [diphenylphosphino]propane (DPPP), and Bu3P [J].
Harayama, T ;
Akiyama, T ;
Nakano, Y ;
Nishioka, H ;
Abe, H ;
Takeuchi, Y .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (04) :519-522
[5]   ISOCARBOSTYRILS .1. ELECTROPHILIC SUBSTITUTION REACTIONS [J].
HORNING, DE ;
LACASSE, G ;
MUCHOWSK.JM .
CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (17) :2785-&
[6]   SYNTHESIS OF PHENANTHRIDIN-6-ONES FROM 3.4-DISUBSTITUTED COUMARINS AND THEIR REACTION WITH METHYLMAGNESIUM IODIDE TO PHENANTHRIDINIUM IODIDES [J].
KRAATZ, U ;
KORTE, F .
CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (01) :62-68
[7]   CHEMISTRY OF NARCICLASINE [J].
MONDON, A ;
KROHN, K .
CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (02) :445-463
[8]   SYNTHETIC APPLICATION OF LITHIATION REACTIONS .14. NOVEL SYNTHESIS OF 7,8-DIMETHOXY PHENANTHRIDINE [J].
NARASIMHAN, NS ;
CHANDRACHOOD, PS ;
SHETE, NR .
TETRAHEDRON, 1981, 37 (04) :825-827
[9]  
OKAMOTO T, 1968, CHEM PHARM BULL, V16, P1860
[10]   Addition of alkyl and aryl isocyanides to benzyne [J].
Rigby, JH ;
Laurent, S .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6742-6744