Fe(OTf)3-Catalyzed Aromatization of Substituted 3-Methyleneindoline and Benzofuran Derivatives: A Selective Route to C-3-Alkylated Indoles and Benzofurans

被引:28
作者
Kundal, Sandip [1 ]
Jalal, Swapnadeep [1 ]
Paul, Kartick [1 ]
Jana, Umasish [1 ]
机构
[1] Jadavpur Univ, Dept Chem, Kolkata 700032, W Bengal, India
关键词
Indoles; Benzofurans; Aromatization; Iron; Isomerization; Homogeneous catalysis; ALKYNE; FUNCTIONALIZATION; ALKYLATION; ALKALOIDS;
D O I
10.1002/ejoc.201500540
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and convenient approach was developed to the selective synthesis of 3-substituted indoles and benzofurans by the isomerization of 3-methyleneindoline and benzofuran derivatives catalyzed by Fe(OTf)(3). The salient features of this method are the easy availability of substrates, high yield, mild reaction conditions, tolerance of a variety of functional groups, and use of an environmentally friendly catalyst. A possible mechanism has also been proposed for the isomerization process.
引用
收藏
页码:5513 / 5517
页数:5
相关论文
共 34 条
[1]   Palladium-Catalyzed Cascade Reactions of 1-(3-Arylprop-2-ynyloxy)-2-bromo Benzene Derivatives with Organoboron Compounds [J].
Arcadi, Antonio ;
Blesi, Federico ;
Cocchi, Sandro ;
Fabrizi, Giancarlo ;
Goggiamani, Antonella ;
Marinelli, Fabio .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (09) :4490-4498
[2]   Scandium Triflate-Catalyzed Nucleophilic Additions to Indolylmethyl Meldrum's Acid Derivatives via a Gramine-Type Fragmentation: Synthesis of Substituted Indolemethanes [J].
Armstrong, Erin L. ;
Grover, Huck K. ;
Kerr, Michael A. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) :10534-10540
[3]   A journey across recent advances in catalytic and stereoselective alkylation of indoles [J].
Bandini, M ;
Melloni, A ;
Tommasi, S ;
Umani-Ronchi, A .
SYNLETT, 2005, (08) :1199-1222
[4]  
Bandini M., 2009, ANGEW CHEM, V121, P9786, DOI DOI 10.1002/ange.200901843
[5]   Catalytic Functionalization of Indoles in a New Dimension [J].
Bandini, Marco ;
Eichholzer, Astrid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644
[6]   Recent Advances in the Synthesis of Indole and Quinoline Derivatives through Cascade Reactions [J].
Barluenga, Jose ;
Rodriguez, Felix ;
Fananas, Francisco J. .
CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (07) :1036-1048
[7]   FeCl3-catalyzed synthesis of functionally diverse dibenzo[b,f]oxepines and benzo[b]oxepines via alkyne-aldehyde metathesis [J].
Bera, Krishnendu ;
Jalal, Swapnadeep ;
Sarkar, Soumen ;
Jana, Umasish .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (01) :57-61
[8]   Synthesis of Substituted Phenanthrene by Iron(III)-Catalyzed Intramolecular Alkyne-Carbonyl Metathesis [J].
Bera, Krishnendu ;
Sarkar, Soumen ;
Jalal, Swapnadeep ;
Jana, Umasish .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19) :8780-8786
[9]   Iron-Catalyzed Synthesis of Functionalized 2H-Chromenes via Intramolecular Alkyne-Carbonyl Metathesis [J].
Bera, Krishnendu ;
Sarkar, Soumen ;
Biswas, Srijit ;
Maiti, Sukhendu ;
Jana, Umasish .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) :3539-3544
[10]  
Biswal S., 2012, ASIAN J PHARM CLIN R, V5, P1