Redox-Neutral Indole Annulation Cascades

被引:178
作者
Haibach, Michael C. [1 ]
Deb, Indubhusan [1 ]
De, Chandra Kanta [1 ]
Seidel, Daniel [1 ]
机构
[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
基金
美国国家科学基金会;
关键词
C-H BOND; RING-CLOSURE REACTIONS; NITROGEN-CONTAINING HETEROCYCLES; ONE-POT SYNTHESIS; INTERMOLECULAR REACTIONS; CYCLOADDITION REACTION; CATALYZED CYCLIZATION; 1,5-HYDRIDE SHIFTS; ORGANIC-SYNTHESIS; ALKYNYL ETHERS;
D O I
10.1021/ja110713k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Aminobenzaldehydes react with indoles in an unprecedented cascade reaction. This acid-catalyzed redox-neutral annulation proceeds via a condensation/1,5-hydride shift/ring-closure sequence. Polycyclic azepinoindoles and related compounds are obtained in a single step with good to excellent yields.
引用
收藏
页码:2100 / 2103
页数:4
相关论文
共 99 条
[91]   Privileged scaffolds for library design and drug discovery [J].
Welsch, Matthew E. ;
Snyder, Scott A. ;
Stockwell, Brent R. .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (03) :347-361
[92]  
Wölfling J, 1999, ANGEW CHEM INT EDIT, V38, P200, DOI 10.1002/(SICI)1521-3773(19990115)38:1/2<200::AID-ANIE200>3.0.CO
[93]  
2-L
[94]   Synthesis of novel d-secoestrone isoquinuclidines by an unpredicted iminium ion-induced 1,5-hydride shift [J].
Wölfling, J ;
Frank, E ;
Schneider, G ;
Tietze, LF .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (01) :90-100
[95]   α-amination of nitrogen heterocycles:: Ring-fused aminals [J].
Zhang, Chen ;
De, Chandra Kanta ;
Mal, Rudrajit ;
Seidel, Daniel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :416-+
[96]   Azomethine ylide annulations: facile access to polycyclic ring systems [J].
Zhang, Chen ;
Das, Deepankar ;
Seidel, Daniel .
CHEMICAL SCIENCE, 2011, 2 (02) :233-236
[97]   Nontraditional Reactions of Azomethine Ylides: Decarboxylative Three-Component Couplings of α-Amino Acids [J].
Zhang, Chen ;
Seidel, Daniel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) :1798-+
[98]   Facile Formation of Cyclic Aminals through a Bronsted Acid-Promoted Redox Process [J].
Zhang, Chen ;
Murarka, Sandip ;
Seidel, Daniel .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01) :419-422
[99]  
ZHOU G, 2010, J CHEM SOC CHEM COMM, V46, P6593