A highly efficient and selective AuI-catalyzed tandem synthesis of diversely substituted pyrrolo[1,2-a]quinolines in aqueous media

被引：136
作者：
Liu, Xin-Yuan [1 ]
Che, Chi-Ming [1 ]
机构：
[1] Univ Hong Kong, Inst Mol Technol Drug Discovery & Synth, Dept Chem, Hong Kong, Hong Kong, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 20期
关键词：
alkynes; gold; pyrrolo[1,2-a]quinolines; tandem reactions; water chemistry;
D O I：
10.1002/anie.200800160
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Bicycles built in water: The Au I-catalyzed tandem cyclization of 1-amino-4-alkynes with alkynes in water offers a simple and efficient method for the synthesis of diversely substituted pyrrolo[1,2-a]quinolines with good to excellent product yields and excellent regio- and chemoselectivities (see scheme). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：3805 / 3810
页数：6
相关论文
共 85 条
[1]   Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations [J].
Ajamian, A ;
Gleason, JL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3754-3760
[2]  
Ajamian A., 2004, ANGEW CHEM, V116, P3842
[3]   VYNYLOGOUS CARBINOLAMINE TUMOR INHIBITORS .23. SYNTHESIS AND ANTILEUKEMIC ACTIVITY OF BIS[[(CARBAMOYL)OXY]METHYL]-SUBSTITUTED PYRROLO[I,1-A]ISOQUINOLINES, PYRROLO[1,2-A]QUINOLINES, PYRROLO[2,1-A]ISOBENZAZEPINES, AND PYRROLO[1,2-A]BENZAZEPINES [J].
ANDERSON, WK ;
HEIDER, AR ;
RAJU, N ;
YUCHT, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (11) :2097-2102
[4]  
[Anonymous], ANGEW CHEM
[5]   Recent applications of gold catalysis in organic synthesis [J].
Arcadi, A ;
Di Giuseppe, S .
CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) :795-812
[6]   Gold- or platinum-catalyzed tandem cycloisomerization/Prins-type cyclization reactions [J].
Barluenga, J ;
Diéguez, A ;
Fernández, A ;
Rodríguez, F ;
Fañanás, FJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (13) :2091-2093
[7]  
BARLUENGA J, 2006, ANGEW CHEM, V118, P2145
[8]   Determining the geometries of transition states by use of antihydrophohic additives in water [J].
Breslow, R .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (07) :471-478
[9]   Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans [J].
Buzas, A ;
Istrate, F ;
Gagosz, F .
ORGANIC LETTERS, 2006, 8 (09) :1957-1959
[10]   Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones [J].
Buzas, Andrea ;
Gagosz, Fabien .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12614-12615
123456789