Synthesis of isoquinolines and naphthyridines by electrophilic ring closure of iminoalkynes

被引:138
作者
Huang, QH [1 ]
Hunter, JA [1 ]
Larock, RC [1 ]
机构
[1] Iowa State Univ Sci & Technol, Dept Chem, Ames, IA 50011 USA
关键词
D O I
10.1021/ol010136h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Substituted isoquinolines and naphthyridines have been prepared in good to excellent yields by the reaction of iminoalkynes with a variety of electrophiles under mild reaction conditions.
引用
收藏
页码:2973 / 2976
页数:4
相关论文
共 21 条
[1]  
ANDERSON CD, 1980, J CHEM SOC P1, P1331
[2]   A new approach to 2,3-disubstituted benzo[b]furans from o-alkynylphenols via 5-endo-dig-iodocyclisation/palladium-catalysed reactions [J].
Arcadi, A ;
Cacchi, S ;
Fabrizi, G ;
Marinelli, F ;
Moro, L .
SYNLETT, 1999, (09) :1432-1434
[3]   A NEW VERSATILE SYNTHESIS OF ISOQUINOLINES BY CONDENSATION OF IMINOPHOSPHORANES WITH ORTHO-PHTHALALDEHYDE [J].
AUBERT, T ;
FARNIER, M ;
HANQUET, B ;
GUILARD, R .
SYNTHETIC COMMUNICATIONS, 1987, 17 (15) :1831-1837
[4]  
BOBBITT JM, 1987, HETEROCYCLES, V25, P601
[5]   A NEW PREPARATION OF DIFUNCTIONALIZED ENAMINES FROM THIOAMIDES USING SILVER(I) CARBONATE [J].
BRILLON, D ;
SAUVE, G .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2246-2249
[6]   First synthesis of the antimalarial naphthylisoquinoline alkaloid dioncophylline C, and its unnatural anti-HIV dimer, jozimine C [J].
Bringmann, G ;
Holenz, J ;
Weirich, R ;
Rübenacker, M ;
Funke, C ;
Boyd, MR ;
Gulakowski, RJ ;
François, G .
TETRAHEDRON, 1998, 54 (3-4) :497-512
[7]  
BROSSI A, 1988, HETEROCYCLES, V12, P2905
[8]   Antidesmone, a novel type isoquinoline alkaloid from Antidesma membranaceum (Euphorbiaceae) [J].
Buske, A ;
Busemann, S ;
Mühlbacher, J ;
Schmidt, J ;
Porzel, A ;
Bringmann, G ;
Adam, G .
TETRAHEDRON, 1999, 55 (04) :1079-1086
[9]   Synthesis of isoquinolines and pyridines via palladium-catalysed iminoannulation of allenes [J].
Diederen, JJH ;
Sinkeldam, RW ;
Frühauf, HW ;
Hiemstra, H ;
Vrieze, K .
TETRAHEDRON LETTERS, 1999, 40 (22) :4255-4258
[10]   REACTION OF BENZOCYCLOBUTENOXIDES WITH NITRILES - SYNTHESIS OF HYPECUMINE AND OTHER 3-SUBSTITUTED ISOQUINOLINES [J].
FITZGERALD, JJ ;
MICHAEL, FE ;
OLOFSON, RA .
TETRAHEDRON LETTERS, 1994, 35 (49) :9191-9194