Facile Synthesis of Trisubstituted Carbazoles by Acid-Catalyzed Ring-Opening Annulation of 2-Amidodihydrofurans with Indoles

被引：35
作者：
Zhao, Jingjing [1 ,2 ]
Li, Pan [1 ]
Xia, Chungu [1 ]
Li, Fuwei [1 ]
机构：
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth Oxidat, Lanzhou 730000, Peoples R China
[2] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 46期
基金：
中国国家自然科学基金;
关键词：
acid-catalysis; carbazoles; chemoselectivity; regioselectivity; ring-opening annulation; TRANSITION-METAL-COMPLEXES; C BOND-CLEAVAGE; 1,3-DICARBONYL COMPOUNDS; DIRECT CARBONYLATION; ORGANIC-SYNTHESIS; PI-EXTENSION; CLAUSINE-L; EFFICIENT; ALKALOIDS; FUNCTIONALIZATION;
D O I：
10.1002/chem.201503260
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A mild and convenient synthesis of carbazoles by TfOTMS (trimethylsilyl trifluoromethanesulfonate)-catalyzed ring-opening annulation of 2-amidodihydrofurans is presented with a high degree of chemoselectivity and regioselectivity. This procedure was also scaled up to a gram-scale synthesis. The reaction could involve an iminonium intermediate through a series of CO, CN bond cleavages, CC bond formations, and a 1,2-migration process.
引用
收藏
页码：16383 / 16386
页数：4
相关论文
共 56 条
[1]   Solvent-free solid acid-catalyzed electrophilic annelations:: A new green approach for the synthesis of substituted five-membered N-heterocycles [J].
Abid, Mohammed ;
Spaeth, Andrew ;
Torok, Bela .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) :2191-2196
[2]   Gold- or Palladium-Catalyzed Allene Carbocyclization/Functionalization: Simple and Efficient Synthesis of Carbazoles [J].
Alcaide, Benito ;
Almendros, Pedro ;
Alonso, Jose M. ;
Teresa Quiros, M. ;
Gadzinski, Pawel .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) :1871-1876
[3]   Palladium(II)/Copper Halide/Solvent Combination for Selective Intramolecular Domino Reactions of Indolecarboxylic Acid Allylamides: An Unprecedented Arylation/Esterification Sequence [J].
Broggini, Gianluigi ;
Barbera, Vincenzina ;
Beccalli, Egle M. ;
Borsini, Elena ;
Galli, Simona ;
Lanza, Giuseppe ;
Zecchi, Gaetano .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (01) :159-170
[4]   Transition metal complexes inorganic synthesis, Part 77.: First enantioselective total synthesis of neocarazostatin B, determination of its absolute configuration and transformation into carquinostatin A [J].
Czerwonka, R ;
Reddy, KR ;
Baum, E ;
Knölker, HJ .
CHEMICAL COMMUNICATIONS, 2006, (07) :711-713
[5]   Transition metals in organic synthesis, part 87:: An efficient palladium-catalyzed route to 2-oxygenated and 2,7-dioxygenated carbazole alkaloids -: Total synthesis of 2-methoxy-3-methylcarbazole, glycosinine, clausine L, mukonidine, and clausine V [J].
Forke, Ronny ;
Krahl, Micha P. ;
Daebritz, Frank ;
Jager, Anne ;
Knoelker, Hans-Joachim .
SYNLETT, 2008, (12) :1870-1876
[6]   First total synthesis of clausine L and pityriazole, a metabolite of the human pathogenic yeast Malassezia furfur [J].
Forke, Ronny ;
Jaeger, Anne ;
Knoelker, Hans-Joachim .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (14) :2481-2483
[7]  
Gallagher P.T., 2000, SCI SYNTHESIS, V10, P693
[8]   Total synthesis of the cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids derived from 2-hydroxy-6-methylcarbazole [J].
Gassner, Cemena ;
Hesse, Ronny ;
Schmidt, Arndt W. ;
Knoelker, Hans-Joachim .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (33) :6490-6499
[9]   Snapshot of the Palladium(II)-Catalyzed Oxidative Biaryl Bond Formation by X-ray Analysis of the Intermediate Diaryl Palladium(II) Complex [J].
Gensch, Tobias ;
Roennefahrt, Marika ;
Czerwonka, Regina ;
Jaeger, Anne ;
Kataeva, Olga ;
Bauer, Ingmar ;
Knoelker, Hans-Joachim .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (03) :770-776
[10]   First Inverse Electron-Demand Diels-Alder Methodology of 3-Chloroindoles and Methyl Coumalate to Carbazoles [J].
Guney, Tezcan ;
Lee, Jennifer J. ;
Kraus, George A. .
ORGANIC LETTERS, 2014, 16 (04) :1124-1127
123456