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

被引：27
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
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 12期
基金：
美国国家科学基金会; 美国国家卫生研究院;
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 ; 081704 ;
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
    Bräse, S
    Gil, C
    Knepper, K
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) : 2415 - 2437
  • [2] Indolyne and Aryne Distortions and Nucleophilic Regioselectivites
    Cheong, Paul H. -Y.
    Paton, Robert S.
    Bronner, Sarah M.
    Im, G-Yoon J.
    Garg, Neil K.
    Houk, K. N.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) : 1267 - +
  • [3] Ruthenium metallopharmaceuticals (vol 232, pg 69, 2002)
    Clarke, MJ
    [J]. 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
    Di Cosimo, S
    Ferretti, G
    Papaldo, P
    Carlini, P
    Fabi, A
    Cognetti, F
    [J]. 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
    Dubrovskiy, Anton V.
    Larock, Richard C.
    [J]. ORGANIC LETTERS, 2011, 13 (15) : 4136 - 4139
  • [7] Radical scavenger activity of bendazac, an anticataract non-steroidal anti-inflammatory agent
    Guglielmotti, A
    DeJoannon, AC
    Cazzolla, N
    Marchetti, M
    Soldo, L
    Cavallo, G
    Pinza, M
    [J]. 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
    HIMESHIMA, Y
    SONODA, T
    KOBAYASHI, H
    [J]. CHEMISTRY LETTERS, 1983, (08) : 1211 - 1214
  • [10] A Review of Granisetron, 5-Hydroxytryptamine3 Receptor Antagonists, and Other Antiemetics
    Hsu, Eric S.
    [J]. AMERICAN JOURNAL OF THERAPEUTICS, 2010, 17 (05) : 476 - 486
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