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Ruthenium-catalyzed regioselective synthesis of 2-substituted indoles via ring-opening of epoxides by anilines

被引：30
作者：
Cho, CS [1 ]
Kim, JH
Choi, HJ
Kim, TJ
Shim, SC
机构：
[1] Kyungpook Natl Univ, Ind Technol Res Inst, Taegu 702701, South Korea
[2] Kyungpook Natl Univ, Dept Ind Chem, Taegu 702701, South Korea
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 14期
基金：
新加坡国家研究基金会;
关键词：
anilines; epoxides; indoles; ring-opening; ruthenium catalyst;
D O I：
10.1016/S0040-4039(03)00396-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Anilines react with epoxides in dioxane at 180degreesC in the presence of a catalytic amount of a ruthenium catalyst along with tin(II) chloride to afford 2-substituted indoles in moderate to good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2975 / 2977
页数：3
相关论文
共 26 条
[1]   Synthesis of quinolines via ruthenium-catalysed amine exchange reaction between anilines and trialkylamines [J].
Cho, CS ;
Oh, BH ;
Kim, JS ;
Kim, TJ ;
Shim, SC .
CHEMICAL COMMUNICATIONS, 2000, (19) :1885-1886
[2]   Ruthenium-catalyzed regioselective α-alkylation of ketones with primary alcohols [J].
Cho, CS ;
Kim, BT ;
Kim, TJ ;
Shim, SC .
TETRAHEDRON LETTERS, 2002, 43 (44) :7987-7989
[3]   An unusual type of ruthenium-catalyzed transfer hydrogenation of ketones with alcohols accompanied by C-C coupling [J].
Cho, CS ;
Kim, BT ;
Kim, TJ ;
Shim, SC .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :9020-9022
[4]   Ruthenium-catalysed oxidative cyclisation of 2-aminobenzyl alcohol with ketones: modified Friedlaender quinoline synthesis [J].
Cho, CS ;
Kim, BT ;
Kim, TJ ;
Shim, SC .
CHEMICAL COMMUNICATIONS, 2001, (24) :2576-2577
[5]   Ruthenium-catalyzed reductive cyclization of nitroarenes with trialkylamines leading to quinolines [J].
Cho, CS ;
Kim, TK ;
Kim, BT ;
Kim, TJ ;
Shim, SC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 650 (1-2) :65-68
[6]   Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles [J].
Cho, CS ;
Kim, JH ;
Kim, TJ ;
Shim, SC .
TETRAHEDRON, 2001, 57 (16) :3321-3329
[7]   Ruthenium-catalysed synthesis of indoles from anilines and trialkanolamines in the presence of tin(II) chloride dihydrate [J].
Cho, CS ;
Lim, HK ;
Shim, SC ;
Kim, TJ ;
Choi, HJ .
CHEMICAL COMMUNICATIONS, 1998, (09) :995-996
[8]   Ruthenium-catalyzed synthesis of indoles from anilines and trialkanolammonium chlorides in an aqueous medium [J].
Cho, CS ;
Kim, JH ;
Shim, SC .
TETRAHEDRON LETTERS, 2000, 41 (11) :1811-1814
[9]   Synthesis of quinolines by ruthenium-catalyzed heteroannulation of anilines with 3-amino-1-propanol [J].
Cho, CS ;
Oh, BH ;
Shim, SC .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (05) :1175-1178
[10]   Ruthenium-catalyzed synthesis of quinolines from anilines and allylammonium chlorides in an aqueous medium via amine exchange reaction [J].
Cho, CS ;
Kim, JS ;
Oh, BH ;
Kim, TJ ;
Shim, SC ;
Yoon, NS .
TETRAHEDRON, 2000, 56 (39) :7747-7750
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