Synthesis of fused indoles by sequential palladium-catalyzed Heck reaction and N-heteroannulation

被引:43
作者
Söderberg, BCG [1 ]
Hubbard, JW [1 ]
Rector, SR [1 ]
O'Neil, SN [1 ]
机构
[1] W Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26506 USA
基金
美国国家卫生研究院;
关键词
palladium-catalyzed; indoles; reductive; annulation;
D O I
10.1016/j.tet.2005.02.033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A route to 3,4-fused indoles via two consecutive palladium-catalyzed reactions; an intramolecular Heck reaction followed by a reductive N-heteroannulation is described. Using this route, a number of indoles have been prepared having a variety of ring sizes anchored to the 3- and 4-position of the indole nucleus. Furthermore, a number of functional groups, both carbon and heteroatom substituents can be introduced in (and on) the additional ring without any detrimental effects on the two reactions. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3637 / 3649
页数:13
相关论文
共 30 条
[1]   PALLADIUM COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION OF NITROARENES - NOVEL SYNTHESIS OF INDOLE AND 2H-INDAZOLE DERIVATIVES [J].
AKAZOME, M ;
KONDO, T ;
WATANABE, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3375-3380
[2]   Cyclopalladation of the primary amine (R)-(+)-1-(1-naphthyl)ethylamine: A new resolving agent for monodentate phosphines [J].
Albert, J ;
Cadena, JM ;
Granell, J .
TETRAHEDRON-ASYMMETRY, 1997, 8 (07) :991-994
[3]   A mild and efficient procedure for the oxidation of organic sulfides to sulfones by use of urea-hydrogen peroxide trifluoroacetic anhydride system [J].
Balicki, R .
SYNTHETIC COMMUNICATIONS, 1999, 29 (13) :2235-2239
[4]   Palladium (II) acetate-tris(triphenylphosphine)rhodium(I) chloride: A novel catalytic couple for the intramolecular Heck reaction [J].
Bankston, D ;
Fang, F ;
Huie, E ;
Xie, SP .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3461-3466
[5]  
CENINI S, 1997, REDUCTIVE CARBONYLAT
[6]   DEOXYGENATION REACTIONS OF ORTHO-NITROSTYRENES WITH CARBON-MONOXIDE CATALYZED BY METAL-CARBONYLS - A NEW ROUTE TO INDOLES [J].
CROTTI, C ;
CENINI, S ;
RINDONE, B ;
TOLLARI, S ;
DEMARTIN, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) :784-786
[7]  
CROTTI C, 1991, J CHEM SOC FARADAY T, P2811
[8]   A novel palladium-catalyzed synthesis of β-carbolines:: application in total synthesis of naturally occurring alkaloids [J].
Dantale, SW ;
Söderberg, BCG .
TETRAHEDRON, 2003, 59 (29) :5507-5514
[9]   PYRROLO[4,3,2-DE]ISOQUINOLINES WITH CENTRAL NERVOUS-SYSTEM AND ANTIHYPERTENSIVE ACTIVITIES [J].
DEMERSON, CA ;
PHILIPP, AH ;
HUMBER, LG ;
KRAML, MJ ;
CHAREST, MP ;
TOM, H ;
VAVRA, I .
JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (11) :1140-1145
[10]   Synthesis of the benzophenone fragment of balanol via an intramolecular cyclization event [J].
Denieul, MP ;
Laursen, B ;
Hazell, R ;
Skrydstrup, T .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6052-6060