Easy access to aryl- and heteroaryl-annulated[a]carbazoles by the indium-catalyzed reaction of 2-arylindoles with propargyl ethers

被引:76
作者
Tsuchimoto, T [1 ]
Matsubayashi, H
Kaneko, M
Shirakawa, E
Kawakami, Y
机构
[1] Japan Adv Inst Sci & Technol, Grad Sch Mat Sci, Tatsunokuchi, Ishikawa 9231292, Japan
[2] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
关键词
annulation; fused-ring systems; heterocycles; indium; Lewis acids;
D O I
10.1002/anie.200462280
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Indoles and indium: An indium salt catalyzes the assembly of 2-arylindoles and propargyl ethers into diverse aryl- and heteroaryl-annulated[a]carbazoles in a highly regioselective manner, in which two different modes of carbon-carbon bond-forming reactions are successfully incorporated in one step (see scheme). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1336 / 1340
页数:5
相关论文
共 34 条
[1]  
BECCALLI EM, 1992, SYNTHESIS-STUTTGART, P891
[2]   Indolocarbazoles [J].
Bergman, J ;
Janosik, T ;
Wahlström, N .
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 80, 2001, 80 :1-71
[3]   Combined directed ortho and remote metalation -: Cross-coupling strategies.: General method for benzo[a]carbazoles and the synthesis of an unnamed indolo[2,3-a]carbazole alkaloid [J].
Cai, XW ;
Snieckus, V .
ORGANIC LETTERS, 2004, 6 (14) :2293-2295
[4]   DNA binding and topoisomerase I poisoning activities of novel disaccharide indolocarbazoles [J].
Facompre, M ;
Carrasco, C ;
Colson, P ;
Houssier, C ;
Chisholm, JD ;
Van Vranken, DL ;
Bailly, C .
MOLECULAR PHARMACOLOGY, 2002, 62 (05) :1215-1227
[5]   Synthesis of indolo[2,3-a]carbazole glycoside analogs of rebeccamycin:: inhibitors of cyclin D1-CDK4 [J].
Faul, MM ;
Sullivan, KA ;
Grutsch, JL ;
Winneroski, LL ;
Shih, C ;
Sanchez-Martinez, C ;
Cooper, JT .
TETRAHEDRON LETTERS, 2004, 45 (05) :1095-1098
[6]   A short synthesis of staurosporinone (K-252c) [J].
Gaudêncio, SP ;
Santos, MMM ;
Lobo, AM ;
Prabhakar, S .
TETRAHEDRON LETTERS, 2003, 44 (12) :2577-2578
[7]   Kinetics of the Friedel-Crafts alkylations of heterocyclic arenes:: Comparison of the nucleophilic reactivities of aromatic and nonaromatic π-systems [J].
Gotta, MF ;
Mayr, H .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9769-9775
[8]   The use of the fluorescence properties of indolocarbazole analogs of adenosine triphosphate as probes of the activating conformational change in protein kinase C [J].
Ho, CJ ;
Slater, SJ ;
Stubbs, CD .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2001, 142 (2-3) :163-168
[9]   HARD SOFT ACIDS BASES (HSAB) PRINCIPLE AND ORGANIC-CHEMISTRY [J].
HO, TL .
CHEMICAL REVIEWS, 1975, 75 (01) :1-20
[10]   Cycloisomerization of ω-aryl-1-alkynes:: GaCl3 as a highly electrophilic catalyst for alkyne activation [J].
Inoue, H ;
Chatani, N ;
Murai, S .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1414-1417