Transition-metal-free synthesis of multisubstituted N-arylindoles via reaction of arynes and α-amino ketones

被引:28
作者
He, Lin [1 ]
Pian, Ji-Xin [1 ]
Shi, Jun-Feng [1 ]
Du, Guang-Fen [1 ]
Dai, Bin [1 ]
机构
[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi 832000, Xinjiang Uygur, Peoples R China
基金
中国国家自然科学基金;
关键词
Indoles; Arynes; Cross-coupling reaction; alpha-Amino ketones; SIMPLE INDOLE ALKALOIDS; EFFICIENT SYNTHESIS; OXIDATIVE CYCLIZATION; BOND; BENZYNE; CONSTRUCTION; AMINATION; ARYLATION; CASCADE;
D O I
10.1016/j.tet.2014.02.028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple transition-metal-free protocol for the synthesis of indoles has been developed using aryne cycloaddition. The in situ-generated arynes couple with alpha-amino ketones through a one-step N-arylation-nucleophilic addition process under mild conditions and efficiently produce multi-substituted N-arylindoles. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2400 / 2405
页数:6
相关论文
共 58 条
[1]   TiCl4/t-BuNH2 as the sole catalyst for a hydroamination-based Fischer indole synthesis [J].
Ackermann, L ;
Born, R .
TETRAHEDRON LETTERS, 2004, 45 (52) :9541-9544
[2]   Zinc-promoted hydrohydrazination of terminal alkynes: An efficient domino synthesis of indoles [J].
Alex, Karolin ;
Tillack, Annegret ;
Schwarz, Nicolle ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2304-2307
[3]  
[Anonymous], 2004, MIGRATION NEWS, V11, P8
[4]   Improved Synthesis of the Benzyne Precursor 2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate [J].
Atkinson, Darcy J. ;
Sperry, Jonathan ;
Brimble, Margaret A. .
SYNTHESIS-STUTTGART, 2010, (06) :911-913
[5]   Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones [J].
Bernini, Roberta ;
Fabrizi, Giancarlo ;
Sferrazza, Alessio ;
Cacchi, Sandro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) :8078-8081
[6]   Arynes in Transition-Metal-Free Multicomponent Coupling Reactions [J].
Bhojgude, Sachin Suresh ;
Biju, Akkattu T. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (07) :1520-1522
[7]   Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes [J].
Bhunia, Anup ;
Yetra, Santhivardhana Reddy ;
Biju, Akkattu T. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) :3140-3152
[8]   Heteroannulation of arynes with N-aryl-α-aminoketones for the synthesis of unsymmetrical N-aryl-2,3-disubstituted indoles: an aryne twist of Bischler-Mohlau indole synthesis [J].
Bunescu, Ala ;
Piemontesi, Cyril ;
Wang, Qian ;
Zhu, Jieping .
CHEMICAL COMMUNICATIONS, 2013, 49 (87) :10284-10286
[9]   Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions [J].
Cacchi, Sandro ;
Fabrizi, Giancarlo .
CHEMICAL REVIEWS, 2011, 111 :PR215-PR283
[10]   The Benzyne Aza-Claisen Reaction [J].
Cant, Alastair A. ;
Bertrand, Guillaume H. V. ;
Henderson, Jaclyn L. ;
Roberts, Lee ;
Greaney, Michael F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5199-5202