Iodine-Catalyzed Oxidative Cross-Coupling of Indoles and Azoles: Regioselective Synthesis of N-Linked 2-(Azol-1-yl)indole Derivatives

被引：65
作者：
Beukeaw, Danupat
Udomsasporn, Kwanchanok
Yotphan, Sirilata [1 ]
机构：
[1] Mahidol Univ, Fac Sci, Ctr Catalysis, Bangkok 10400, Thailand
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 07期
关键词：
ANTIMITOTIC BICYCLIC PEPTIDES; CONCISE TOTAL-SYNTHESIS; AMINATION; KETONES; SEEDS; FUNCTIONALIZATION; AMIDATION; MOROIDIN; ACCESS; HYDROARYLATION;
D O I：
10.1021/jo502933e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient iodine-catalyzed regioselective oxidative cross-coupling of an indole C-H bond and azole N-H bond is described. This metal-free reaction can be easily carried out at room temperature under mild and environmentally friendly conditions and provides a series of N-linked 2-(azol-1-yl)indole derivatives in moderate to excellence yields.
引用
收藏
页码：3447 / 3454
页数：8
相关论文
共 63 条
[1]   Cardioprotective activity of melatonin and its novel synthesized derivatives on doxorubicin-induced cardiotoxicity [J].
Ahmed, HH ;
Mannaa, F ;
Elmegeed, GA ;
Doss, SH .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (05) :1847-1857
[2]   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
[3]   Catalytic Functionalization of Indoles in a New Dimension [J].
Bandini, Marco ;
Eichholzer, Astrid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644
[4]   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
[5]   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
[6]   Iodine-Catalyzed Oxidative Amination of Sodium Sulfinates: A Convenient Approach to the Synthesis of Sulfonamides under Mild Conditions [J].
Buathongjan, Chonchanok ;
Beukeaw, Danupat ;
Yotphan, Sirilata .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (07) :1575-1582
[7]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
[8]   I2/TBHP-Catalyzed Chemoselective Amination of Indoles [J].
Cai, Zhong-Jian ;
Wang, Shun-Yi ;
Ji, Shun-Jun .
ORGANIC LETTERS, 2013, 15 (20) :5226-5229
[9]  
COMBER MF, 1992, SYNTHESIS-STUTTGART, P731
[10]   Gold-catalyzed cycloisomerization of N-propargylindole-2-carboxamides:: Application toward the synthesis of lavendamycin analogues [J].
England, Dylan B. ;
Padwa, Albert .
ORGANIC LETTERS, 2008, 10 (16) :3631-3634
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