A general intramolecular Friedel-Crafts approach to functionalized pyrrolo[3,2,1-ij]quinolin-4-ones

被引：18
作者：
Patil, Dadasaheb V. [1 ]
Cavitt, Marchello A. [1 ]
Grzybowski, Paul [1 ]
France, Stefan [1 ]
机构：
[1] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA
来源：
CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 83期
基金：
美国国家科学基金会;
关键词：
EFFICIENT SYNTHESIS; DERIVATIVES; ALKYLATION; CYCLIZATION;
D O I：
10.1039/c2cc34650h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An indium(III)-catalyzed intramolecular Friedel-Crafts annulation for the efficient synthesis of pyrrolo[3,2,1-ij]quinolin-4-ones is described. The products are formed in good to excellent yields (51-97%) with diastereoselectivities up to >99 : 1 dr.
引用
收藏
页码：10337 / 10339
页数：3
相关论文
共 33 条
  • [1] An efficient one-pot synthesis of 4H-pyrrolo[3,2,1-ij]quinolines
    Adib, M
    Sayahi, MH
    [J]. MONATSHEFTE FUR CHEMIE, 2006, 137 (02): : 207 - 211
  • [2] Cyclization of free radicals at the C-7 position of ethyl indole-2-carboxylate derivatives: an entry to a new class of duocarmycin analogues
    Al-Said, NH
    Shawakfeh, KQ
    Abdullah, WN
    [J]. MOLECULES, 2005, 10 (12) : 1446 - 1457
  • [3] 5-imidazolyl-quinolinones, -quinazolinones and -benzo-azepinones as farnesyltransferase inhibitors
    Angibaud, P
    Bourdrez, X
    Devine, A
    End, DW
    Freyne, E
    Ligny, Y
    Muller, P
    Mannens, G
    Pilatte, I
    Poncelet, V
    Skrzat, S
    Smets, G
    Van Dun, J
    Van Remoortere, P
    Venet, M
    Wouters, W
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (09) : 1543 - 1547
  • [4] Ashwell M. A., 2011, U.S. Patent, Patent No. [US 7960134, 7960134]
  • [5] New mesoionic systems of azolopyridine series -: 2.* Synthesis, structures, and biological activity of 2-aminothiazolo[3,2-a]pyridinium salts and thiazolo[3,2-a]pyridinium 2-imidates
    Babaev, EV
    Bush, AA
    Orlova, IA
    Rybakov, VB
    Iwataki, I
    [J]. RUSSIAN CHEMICAL BULLETIN, 2005, 54 (01) : 231 - 237
  • [6] Chemoselective Asymmetric N-Allylic Alkylation of Indoles with Morita-Baylis-Hillman Carbonates
    Cui, Hai-Lei
    Feng, Xin
    Peng, Jing
    Lei, Jie
    Jiang, Kun
    Chen, Ying-Chun
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) : 5737 - 5740
  • [7] C-C bond formation via C-H bond activation: Synthesis of the core of teleocidin B4
    Dangel, BD
    Godula, K
    Youn, SW
    Sezen, B
    Sames, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) : 11856 - 11857
  • [8] Development of an efficient synthesis of the pyrrolquinolone PHA-529311
    Dorow, RL
    Herrinton, PM
    Hohler, RA
    Maloney, MT
    Mauragis, MA
    McGhee, WE
    Moeslein, JA
    Strohbach, JW
    Veley, MF
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (03) : 493 - 499
  • [9] Inhibition of herpesvirus replication by a series of 4-oxo-dihydroquinolines with viral polyrnerase activity
    Hartline, CB
    Harden, EA
    Williams-Aziz, SL
    Kushner, NL
    Brideau, RJ
    Kern, ER
    [J]. ANTIVIRAL RESEARCH, 2005, 65 (02) : 97 - 105
  • [10] Pyrrolo[3,2,1-ij]quinoline derivatives, a 5-HT2c receptor agonist with selectivity over the 5-HT2a receptor:: Potential therapeutic applications for epilepsy and obesity
    Isaac, M
    Slassi, A
    O'Brien, A
    Edwards, L
    MacLean, N
    Bueschkens, D
    Lee, DKH
    McCallum, K
    De Lannoy, I
    Demchyshyn, L
    Kamboj, R
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (09) : 919 - 921
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