Dirhodium(II) Carboxylate Catalyzed Formation of 1,2,3-Trisubstituted Indoles from Styryl Azides

被引:62
作者
Jones, Crystalann [1 ]
Quyen Nguyen [1 ]
Driver, Tom G. [1 ]
机构
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
基金
美国国家卫生研究院;
关键词
azides; electrocyclic reactions; indole; rhodium; synthetic methods; C-H AMINATION; BOND AMINATION; ARYL AZIDES; PHOTO-ISOMERIZATION; IMIDO COMPLEXES; AROMATIC-AMINES; ONE-POT; CONVERSION; ALKALOIDS; 2-ALKYLIDENECYCLOPENTANONES;
D O I
10.1002/anie.201308611
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Dirhodium(II)-carboxylate complexes were discovered to promote the selective migration of acyl groups in trisubstituted styryl azides to form 1,2,3-trisubstituted indoles. The styryl azides are readily available in three steps from cyclobutanone and 2-iodoaniline.
引用
收藏
页码:785 / 788
页数:4
相关论文
共 55 条
[1]   Palladium-Catalyzed Direct Arylation-Based Domino Synthesis of Annulated N-Heterocycles Using Alkenyl or (Hetero)Aryl 1,2-Dihalides [J].
Ackermann, Lutz ;
Althammer, Andreas ;
Mayer, Peter .
SYNTHESIS-STUTTGART, 2009, (20) :3493-3503
[2]  
[Anonymous], ANGEW CHEM
[3]  
[Anonymous], 2008, ANGEW CHEM, DOI DOI 10.1002/adsc.200900065
[4]  
Badiei Y.M., 2008, ANGEW CHEMIE, V120, P10109
[5]   Copper-Nitrene Complexes in Catalytic C-H Amination [J].
Badiei, Yosra M. ;
Dinescu, Adriana ;
Dai, Xiliang ;
Palomino, Robert M. ;
Heinemann, Frank W. ;
Cundari, Thomas R. ;
Warren, Timothy H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (51) :9961-9964
[6]   A SYNTHETIC ROAD TO THE FOREST OF STRYCHNOS, ASPIDOSPERMA, SCHIZOZYGANE AND EBURNAMINE ALKALOIDS BY WAY OF THE NOVEL PHOTO-ISOMERIZATION [J].
BAN, Y ;
YOSHIDA, K ;
GOTO, J ;
OISHI, T ;
TAKEDA, E .
TETRAHEDRON, 1983, 39 (22) :3657-3668
[7]   NOVEL PHOTO-ISOMERIZATION OF 1-ACYLINDOLES TO 3-ACYLINDOLENINES - GENERAL ENTRY TO THE TOTAL SYNTHESIS OF STRYCHNOS AND ASPIDOSPERMA ALKALOIDS [J].
BAN, Y ;
YOSHIDA, K ;
GOTO, J ;
OISHI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (23) :6990-6992
[8]   Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages [J].
Barral, Karine ;
Moorhouse, Adam D. ;
Moses, John E. .
ORGANIC LETTERS, 2007, 9 (09) :1809-1811
[9]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
[10]   Ruthenium-Catalyzed γ-Carbolinium Ion Formation from Aryl Azides; Synthesis of Dimebolin [J].
Dong, Huijun ;
Latka, Regina T. ;
Driver, Tom G. .
ORGANIC LETTERS, 2011, 13 (10) :2726-2729