Copper-catalyzed tandem reaction between imines and alcohols leading to indoles

被引:45
作者
Kamijo, S
Sasaki, Y
Yamamoto, Y [1 ]
机构
[1] Tohoku Univ, Res Ctr Sustainable Mat Engn, Inst Multidisciplinary Res Adv Mat, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
基金
日本学术振兴会;
关键词
indole; copper catalyst; imine; alkyne; alcohol;
D O I
10.1016/j.tetlet.2003.10.141
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed tandem reaction between 2-alkynyl-N-arylideneanilines and alcohols is found to produce N-(alkoxybenzyl)indoles in good to high yields. A wide variety of substituted N-(alkoxybenzyl)indole derivatives call be synthesized by utilizing this protocol, since the derived indoles are essentially formed by the four-component assemblies of aldehydes, 2-iodoanilines, terminal alkynes, and alcohols. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:35 / 38
页数:4
相关论文
共 27 条
[1]   Functionalized 1,2-dihydronaphthalenes from the Cu(OTf)2-catalyzed [4+2] cycloaddition of o-alkynyl(oxo)benzenes with alkenes [J].
Asao, N ;
Kasahara, T ;
Yamamoto, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) :3504-3506
[2]   Pd(II) acts simultaneously as a Lewis acid and as a transition-metal catalyst: Synthesis of cyclic alkenyl ethers from acetylenic aldehydes [J].
Asao, N ;
Nogami, T ;
Takahashi, K ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :764-765
[3]   Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes [J].
Asao, N ;
Nogami, T ;
Lee, S ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10921-10925
[4]   AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].
Asao, N ;
Takahashi, K ;
Lee, S ;
Kasahara, T ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651
[5]   PALLADIUM-CATALYZED CYCLIZATION OF 2-ALKYNYLANILINES TO 2-SUBSTITUTED INDOLES UNDER AN ACIDIC 2-PHASE SYSTEM [J].
CACCHI, S ;
CARNICELLI, V ;
MARINELLI, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 475 (1-2) :289-296
[6]   INDOLES BENZOFURANS PHTHALIDES AND TOLANES VIA COPPER(1) ACETYLIDES [J].
CASTRO, CE ;
GAUGHAN, EJ ;
OWSLEY, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) :4071-+
[7]   Recent developments in indole ring synthesis-methodology and applications [J].
Gribble, GW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075
[8]   TRANSITION-METALS IN THE SYNTHESIS AND FUNCTIONALIZATION OF INDOLES [J].
HEGEDUS, LS .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (09) :1113-1226
[9]   Efficient construction of indole rings from 2-ethynylaniline derivatives catalyzed by copper(II) salts and its application to the tandem cyclization reactions [J].
Hiroya, K ;
Itoh, S ;
Ozawa, M ;
Kanamori, Y ;
Sakamoto, T .
TETRAHEDRON LETTERS, 2002, 43 (07) :1277-1280
[10]   PALLADIUM CATALYZED REACTION OF 2-ALKYNYLANILINES WITH ALLYL CHLORIDES - FORMATION OF 3-ALLYLINDOLES [J].
IRITANI, K ;
MATSUBARA, S ;
UTIMOTO, K .
TETRAHEDRON LETTERS, 1988, 29 (15) :1799-1802