Assembly of N,N-Disubstituted Hydrazines and 1-Aryl-1H-indazoles via Copper-Catalyzed Coupling Reactions

被引：117
作者：
Xiong, Xiaodong
Jiang, Yongwen
Ma, Dawei [1 ]
机构：
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 10期
基金：
中国国家自然科学基金;
关键词：
UNSYMMETRICAL AZO-COMPOUNDS; FISCHER INDOLE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; INTRAMOLECULAR AMINATION; ARYL IODIDES; N-ARYLATION; DERIVATIVES; EFFICIENT; ANTAGONISTS; INHIBITORS;
D O I：
10.1021/ol300847v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cul-catalyzed coupling of N-acyl-N-substituted hydrazines with aryl iodides takes place at 60-90 degrees C to afford N-acyl-N,N-disubstituted hydrazines regioselectively and thereby gives a facile method for assembling N,N-diaryl hydrazines. N-Acyl-N-substituted hydrazines can also react with 2-bromoarylcaibonylic compounds at 60-125 degrees C under the catalysis of Cul/4-hydroxy-L-proline to provide 1-aryl-1H-indazoles.
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收藏
页码：2552 / 2555
页数：4
相关论文
共 51 条
[1]   Synthesis and evaluation of pyrazolo[3,4-b] pyridines and its structural analogues as TNF-α and IL-6 inhibitors [J].
Bharate, Sandip B. ;
Mahajan, Tushar R. ;
Gole, Yogesh R. ;
Nambiar, Mahesh ;
Matan, T. T. ;
Kulkarni-Almeida, Asha ;
Balachandran, Sarala ;
Junjappa, H. ;
Balakrishnan, Arun ;
Vishwakarma, Ram A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (15) :7167-7176
[2]  
Blatter H., 1968, TETRAHEDRON LETT, V22, P2701
[3]  
Blumenfeld M., 2011, Improvements Relating to Fabric Treatment Compositions, Patent No. [WO 2009065893, 2009065893]
[4]   Mild Ullmann-type biaryl ether formation reaction by combination of ortho-substituent and ligand effects [J].
Cai, Q ;
Zou, BL ;
Ma, DW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) :1276-1279
[5]   Synthesis and antiplatelet activity of ethyl 4-(1-benzyl-1H-indazol-3-yl)benzoate (YD-3) derivatives [J].
Chen, Hua-Sin ;
Kuo, Sheng-Chu ;
Teng, Che-Ming ;
Lee, Fang-Yu ;
Wang, Jih-Pyang ;
Lee, Yu-Chun ;
Kuo, Chiung-Wen ;
Huang, Ching-Che ;
Wu, Chin-Chung ;
Huang, Li-Jiau .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (03) :1262-1278
[6]   Facile palladium-catalysed synthesis of 1-aryl-1H-indazoles from 2-bromobenzaldehydes and arylhydrazines [J].
Cho, CS ;
Lim, DK ;
Heo, NH ;
Kim, TJ ;
Shim, SC .
CHEMICAL COMMUNICATIONS, 2004, (01) :104-105
[7]   Copper-Catalyzed Guanidinylation of Aryl Iodides: The Formation of N,N′-Disubstituted Guanidines [J].
Cortes-Salva, Michelle ;
Nguyen, Be-Lan ;
Cuevas, Javier ;
Pennypacker, Keith R. ;
Antilla, Jon C. .
ORGANIC LETTERS, 2010, 12 (06) :1316-1319
[8]   Discovery of N-[(1-aryl-1H-indazol-5-yl)methyl]amides derivatives as smoothened antagonists for inhibition of the hedgehog pathway [J].
Dessole, Gabriella ;
Branca, Danila ;
Ferrigno, Federica ;
Kinzel, Olaf ;
Muraglia, Ester ;
Palumbi, Maria Cecilia ;
Rowley, Michael ;
Serafini, Sergio ;
Steinkuhler, Christian ;
Jones, Philip .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (15) :4191-4195
[9]   HYDRAZIDES AND THIOHYDRAZIDES AS SOURCES OF CONDENSED OXADIAZINES AND THIADIAZINES, INCLUDING NOVEL AZO DERIVATIVES BASED ON DITHIZONE [J].
ELLIOTT, AJ ;
GIBSON, MS .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (18) :3677-3681
[10]  
Gao M., 2011, CHINESE J CHEM, V19, P1199
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