I2/TBHP-Catalyzed Chemoselective Amination of Indoles

被引：77
作者：
Cai, Zhong-Jian [1 ]
Wang, Shun-Yi [1 ]
Ji, Shun-Jun [1 ]
机构：
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 20期
基金：
中国国家自然科学基金;
关键词：
CONCISE TOTAL-SYNTHESIS; N BOND FORMATION; METAL-FREE ROUTE; CATALYZED SYNTHESIS; ALKALOIDS; FUNCTIONALIZATION; BENZOXAZOLES; DERIVATIVES; IODINE; SERIES;
D O I：
10.1021/ol4023936
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel I-2/TBHP-mediated direct oxidative diamination reaction of indoles with anilines was developed. The reaction proceeded smoothly under aqueous and open air reaction conditions. This protocol provides a practical synthetic method for the synthesis of Tryptanthrin and the construction of N-C3 linked pyrrolidinoindolines which is the core structure of Psychotrimine.
引用
收藏
页码：5226 / 5229
页数：4
相关论文
共 88 条
[1]   Antinociceptive profile of Hodgkinsine [J].
Amador, TA ;
Verotta, L ;
Nunes, DS ;
Elisabetsky, E .
PLANTA MEDICA, 2000, 66 (08) :770-772
[2]  
Anthoni U, 1999, ALKAL CHEM, V13, P163, DOI 10.1016/S0735-8210(99)80025-9
[3]   Direct Azole Amination: C-H Functionalization as a New Approach to Biologically Important Heterocycles [J].
Armstrong, Alan ;
Collins, James C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (13) :2282-2285
[4]   Cascade Palladium- and Copper-Catalysed Aromatic Heterocycle Synthesis: The Emergence of General Precursors [J].
Ball, Catherine J. ;
Willis, Michael C. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (03) :425-441
[5]   Catalytic Functionalization of Indoles in a New Dimension [J].
Bandini, Marco ;
Eichholzer, Astrid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644
[6]   Electrosynthesis of tryptanthrin [J].
Batanero, Belen ;
Barba, Fructuoso .
TETRAHEDRON LETTERS, 2006, 47 (47) :8201-8203
[7]   Catalytic Oxyamidation of Indoles [J].
Beaumont, Stephane ;
Pons, Valerie ;
Retailleau, Pascal ;
Dodd, Robert H. ;
Dauban, Philippe .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (09) :1634-1637
[8]   Oxaziridine-Mediated Oxyamination of Indoles: An Approach to 3-Aminoindoles and Enantiomerically Enriched 3-Aminopyrroloindolines [J].
Benkovics, Tamas ;
Guzei, Ilia A. ;
Yoon, Tehshik P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) :9153-9157
[9]   SPORIDESMINS .16. STRUCTURE OF CHETOMIN, A TOXIC METABOLITE OF CHAETOMIUM-COCHLIODES, BY N-15 AND C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY [J].
BREWER, D ;
MCINNES, AG ;
SMITH, DG ;
TAYLOR, A ;
WALTER, JA ;
LOOSLI, HR ;
KIS, ZL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (10) :1248-1251
[10]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
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