Application of Ynamides in the Synthesis of 2-Amidoindoles

被引:76
作者
Dooleweerdt, Karin [2 ,3 ]
Ruhland, Thomas [1 ]
Skrydstrup, Troels [2 ,3 ]
机构
[1] H Lundbeck & Co AS, DK-2400 Copenhagen, Denmark
[2] Aarhus Univ, Ctr Insoluble Prot Struct inSPIN, Dept Chem, DK-8000 Aarhus C, Denmark
[3] Aarhus Univ, Interdisciplinary Nanosci Ctr, DK-8000 Aarhus C, Denmark
关键词
ONE-POT SYNTHESIS; HIGHLY FUNCTIONALIZED INDOLES; AXIALLY CHIRAL ANILIDES; EFFICIENT SYNTHESIS; SUBSTITUTED YNAMIDES; ALKYNYL BROMIDES; O-HALOANILINES; GENERAL-METHOD; ENE-YNAMIDES; CYCLOADDITIONS;
D O I
10.1021/ol802477d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Pd-catalyzed, one-pot, two-step synthesis of 2-amidoindoles from ynamides and o-lodoanilines Is reported. A key highlight of this sequence is that after the Sonogashira reaction, intramolecular cyclization to the indole occurs spontaneously without activation of the alkyne.
引用
收藏
页码:221 / 224
页数:4
相关论文
共 65 条
[51]   Rhodium(I)-catalyzed [2+2+2] cycloadditions of ynamides in the synthesis of amide-substituted chiral biaryls [J].
Tracey, Michael R. ;
Oppenheimer, Jossian ;
Hsung, Richard P. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) :8629-8632
[52]  
Tsuji J., 2004, PALLADIUM REAGENTS C, P201
[53]   A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles [J].
Yao, Pei-Yuan ;
Zhang, Yu ;
Hsung, Richard P. ;
Zhao, Kang .
ORGANIC LETTERS, 2008, 10 (19) :4275-4278
[54]  
YIEN Y, 2006, J ORG CHEM, V72, P5731
[55]   A two-carbon homologation of aldehydes and ketones using ynamides [J].
You, Lingfeng ;
Al-Rashid, Ziyad F. ;
Figueroa, Ruth ;
Ghosh, Sunil K. ;
Li, Gang ;
Lu, Ting ;
Hsung, Richard P. .
SYNLETT, 2007, (11) :1656-1662
[56]   A highly stereoselective synthesis of chiral α-amino-β-lactams via the Kinugasa reaction employing ynamides [J].
Zhang, Xuejun ;
Hsung, Richard P. ;
Li, Hongyan ;
Zhang, Yu ;
Johnson, Whitney L. ;
Figueroa, Ruth .
ORGANIC LETTERS, 2008, 10 (16) :3477-3479
[57]   A triazole-templated ring-closing metathesis for constructing novel fused and bridged triazoles [J].
Zhang, Xuejun ;
Hsung, Richard P. ;
Li, Hongyan .
CHEMICAL COMMUNICATIONS, 2007, (23) :2420-2422
[58]   Tandem azidination- and hydroazidination-Huisgen [3+2] cycloadditions of ynamides. Synthesis of chiral amide-substituted triazoles [J].
Zhang, Xuejun ;
Hsung, Richard P. ;
You, Lingfeng .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (14) :2679-2682
[59]   Copper salt-catalyzed azide-[3+2] cycloadditions of ynamides and bis-ynamides [J].
Zhang, Xuejun ;
Li, Hongyan ;
You, Lingfeng ;
Tang, Yu ;
Hsung, Richard P. .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2437-2442
[60]   Copper(II)-catalyzed amidations of alkynyl bromides as a general synthesis of ynamides and Z-enamides.: An intramolecular amidation for the synthesis of macrocyclic ynamides [J].
Zhang, Xuejun ;
Zhang, Yanshi ;
Huang, Jian ;
Hsung, Richard P. ;
Kurtz, Kimberly C. M. ;
Oppenheimer, Jossian ;
Petersen, Matthew E. ;
Sagamanova, Irina K. ;
Shen, Lichun ;
Tracey, Michael R. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11) :4170-4177