One-pot synthesis of 1-alkyl-1H-indazoles from 1,1-dialkylhydrazones via aryne annulation

被引:28
作者
Markina, Nataliya A. [1 ]
Dubrovskiy, Anton V. [1 ]
Larock, Richard C. [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
INDAZOLES; EFFICIENT; CHEMISTRY; FACILE;
D O I
10.1039/c2ob07117g
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
The reaction of readily accessible 1,1-dialkylhydrazones with commercially available o-(trimethylsilyl) aryl triflates provides a direct one-step route to pharmaceutically important 1-alkylindazoles. The products are obtained in high yields by one-pot NCS-chlorination/aryne annulation or Ac2O-acylation/ deprotection/aromatization protocols.
引用
收藏
页码:2409 / 2412
页数:4
相关论文
共 21 条
[1]
The recent impact of solid-phase synthesis on medicinally relevant benzoannelated nitrogen heterocycles [J].
Bräse, S ;
Gil, C ;
Knepper, K .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) :2415-2437
[2]
Indolyne and Aryne Distortions and Nucleophilic Regioselectivites [J].
Cheong, Paul H. -Y. ;
Paton, Robert S. ;
Bronner, Sarah M. ;
Im, G-Yoon J. ;
Garg, Neil K. ;
Houk, K. N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1267-+
[3]
Ruthenium metallopharmaceuticals (vol 232, pg 69, 2002) [J].
Clarke, MJ .
COORDINATION CHEMISTRY REVIEWS, 2003, 236 (1-2) :207-+
[4]
Dees EC, 2000, CLIN CANCER RES, V6, P3885
[5]
Lonidamine: Efficacy and safety in clinical trials for the treatment of solid tumors [J].
Di Cosimo, S ;
Ferretti, G ;
Papaldo, P ;
Carlini, P ;
Fabi, A ;
Cognetti, F .
DRUGS OF TODAY, 2003, 39 (03) :157-173
[6]
Synthesis of o-(Dimethylamino)aryl Ketones and Acridones by the Reaction of 1,1-Dialkylhydrazones and Arynes [J].
Dubrovskiy, Anton V. ;
Larock, Richard C. .
ORGANIC LETTERS, 2011, 13 (15) :4136-4139
[7]
Radical scavenger activity of bendazac, an anticataract non-steroidal anti-inflammatory agent [J].
Guglielmotti, A ;
DeJoannon, AC ;
Cazzolla, N ;
Marchetti, M ;
Soldo, L ;
Cavallo, G ;
Pinza, M .
PHARMACOLOGICAL RESEARCH, 1995, 32 (06) :369-373
[8]
Hartmann M., 1995, J INORG BIOCHEM, V59, P214
[9]
FLUORIDE-INDUCED 1,2-ELIMINATION OF ORTHO-TRIMETHYLSILYLPHENYL TRIFLATE TO BENZYNE UNDER MILD CONDITIONS [J].
HIMESHIMA, Y ;
SONODA, T ;
KOBAYASHI, H .
CHEMISTRY LETTERS, 1983, (08) :1211-1214
[10]
A Review of Granisetron, 5-Hydroxytryptamine3 Receptor Antagonists, and Other Antiemetics [J].
Hsu, Eric S. .
AMERICAN JOURNAL OF THERAPEUTICS, 2010, 17 (05) :476-486