Double nucleophilic attack on isocyanide carbon: a synthetic strategy for 7-aza-tetrahydroindoles

被引:24
作者
Li, Yifei [1 ]
Xu, Xianxiu [1 ]
Xia, Chunyu [1 ]
Zhang, Lingjuan [1 ]
Pan, Ling [1 ]
Liu, Qun [1 ]
机构
[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China
关键词
DERIVATIVES; DOMINO; ANNULATION; ALKYNES;
D O I
10.1039/c2cc35896d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel and efficient route for the synthesis of 7-aza-tetrahydroindoles from N-aryl/alkyl-alkenoylacetamides and ethyl isocyanoacetate is described. A mechanism, involving a stepwise [3+2] cycloaddition-intramolecular aza-Michael addition cascade, is proposed that explains the origin of the double nucleophilic attack on the isocyanide carbon atom.
引用
收藏
页码:12228 / 12230
页数:3
相关论文
共 36 条
[1]   Metal-catalyzed regiodivergent cyclization of γ-allenols:: Tetrahydrofurans versus oxepanes [J].
Alcaide, Benito ;
Almendros, Pedro ;
del Campo, Teresa Martinez .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (35) :6684-6687
[2]   Silver-mediated synthesis of heterocycles [J].
Alvarez-Corral, Miriam ;
Munoz-Dorado, Manuel ;
Rodirguez-Garcia, Ignacio .
CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198
[3]   [5+1] annulation: A synthetic strategy for highly substituted phenols and cyclohexenones [J].
Bi, XH ;
Dong, DW ;
Liu, Q ;
Pan, W ;
Zhao, L ;
Li, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4578-4579
[4]   Synthesis of indole derivatives via isocyanides [J].
Campo, J ;
García-Valverde, M ;
Marcaccini, S ;
Rojo, MJ ;
Torroba, T .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (05) :757-765
[5]   [5C+1N] Annulation: a novel synthetic strategy for functionalized 2,3-dihydro-4-pyridones [J].
Dong, DW ;
Bi, XH ;
Liu, Q ;
Cong, FD .
CHEMICAL COMMUNICATIONS, 2005, (28) :3580-3582
[6]   Computation-Guided Development of Au-Catalyzed Cycloisomerizations Proceeding via 1,2-Si or 1,2-H Migrations: Regiodivergent Synthesis of Silylfurans [J].
Dudnik, Alexander S. ;
Xia, Yuanzhi ;
Li, Yahong ;
Gevorgyan, Vladimir .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (22) :7645-7655
[7]   Asymmetric organocatalytic domino reactions [J].
Enders, Dieter ;
Grondal, Christoph ;
Huettl, Matthias R. M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1570-1581
[8]   Regiodivergent Ligand-Controlled Rhodium-Catalyzed [(2+2)+2] Carbocyclization Reactions with Alkyl Substituted Methyl Propiolates [J].
Evans, P. Andrew ;
Sawyer, James R. ;
Inglesby, Phillip A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (33) :5746-5749
[9]   Total synthesis of (±)-perophoramidine [J].
Fuchs, JR ;
Funk, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) :5068-5069
[10]   Silver acetate catalysed cycloadditions of isocyanoacetates [J].
Grigg, R ;
Lansdell, MI ;
Thornton-Pett, M .
TETRAHEDRON, 1999, 55 (07) :2025-2044