Microwave-assisted synthesis of 1-aryl-1H-indazoles via one-pot two-step Cu-catalyzed intramolecular N-arylation of arylhydrazones

被引：83
|
作者：
Pabba, C [1 ]
Wang, HJ [1 ]
Mulligan, SR [1 ]
Chen, ZJ [1 ]
Stark, TM [1 ]
Gregg, BT [1 ]
机构：
[1] Albany Mol Res Inc, Dept Med Chem, Albany, NY 12212 USA
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 44期
关键词：
1H-indazole; hydrazone; copper; cyclization; arylation; microwave irradiation;
D O I：
10.1016/j.tetlet.2005.08.143
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient one-pot two-step microwave procedure was developed for the synthesis of 1-aryl-1H-indazoles. Microwave heating of 2-halobenzaldehydes or 2-haloacetophenones with phenylhydrazines at 160 degrees C for 10 min quantitatively yielded the arylhydrazones, which were further cyclized to give 1-aryl-1H-indazoles via CuI/diamine-catalyzed N-arylation under microwave heating (160 degrees C, 10min). Good to excellent yields were observed for 2-iodo, 2-bromo, and 2-chloro benzaldehydes or acetophenones. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7553 / 7557
页数：5
相关论文
共 50 条
  • [1] Synthesis of 1-aryl-1H-indazoles via palladium-catalyzed intramolecular amination of aryl halides
    Lebedev, AY
    Khartulyari, AS
    Voskoboynikov, AZ
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02): : 596 - 602
  • [2] One-Pot, Two-Step, Microwave-Assisted Palladium-Catalyzed Conversion of Aryl Alcohols to Aryl Fluorides via Aryl Nonaflates
    Wannberg, Johan
    Wallinder, Charlotta
    Unlusoy, Meltem
    Skold, Christian
    Larhed, Mats
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08): : 4184 - 4189
  • [3] Synthesis of N-phenyl- and N-thiazolyl-1H-indazoles by copper-catalyzed intramolecular N-arylation of ortho-chlorinated arylhydrazones
    Barbosa, Yara Cristina Marchioro
    Paveglio, Guilherme Caneppele
    Pereira, Claudio Martin Pereira de
    Moura, Sidnei
    Schwalm, Cristiane Storck
    Casagrande, Gleison Antonio
    Pizzuti, Lucas
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2022, 18 : 1079 - 1087
  • [4] Synthesis of 1-Aryl-1H-indazoles via a Ligand-Free Copper-Catalyzed Intramolecular Amination Reaction
    Gao Mingshan
    Liu Xiujie
    Wang Xianyang
    Cai Qian
    Ding Ke
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (06) : 1199 - 1204
  • [5] Microwave-assisted sequential one-pot protocol to benzothiadiazin-3-one-1,1-dioxides via a copper-catalyzed N-arylation strategy
    Rolfe, Alan
    Hanson, Paul R.
    TETRAHEDRON LETTERS, 2009, 50 (50) : 6935 - 6937
  • [6] Practical One-Pot Two-Step Protocol for the Microwave-Assisted Synthesis of Highly Functionalized Rhodanine Derivatives
    Radi, Marco
    Botta, Lorenzo
    Casaluce, Gianni
    Bernardini, Martina
    Botta, Maurizio
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (01): : 200 - 205
  • [7] Efficient one-pot, two-step, microwave-assisted procedure for the synthesis of polysubstituted 2-aminoimidazoles
    Ermolat'ev, Denis S.
    Babaev, Eugene V.
    Van der Eycken, Erik V.
    ORGANIC LETTERS, 2006, 8 (25) : 5781 - 5784
  • [8] One-Pot Two-Step Microwave-Assisted Synthesis of Alkylidene Acetoacetamido Esters, Useful Intermediates for β-Dehydropeptides
    Viola, Angelo
    Ferrazzano, Lucia
    Greco, Roberto
    Cerisoli, Lucia
    Caldi, Jonathan
    Tolomelli, Alessandra
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (19) : 3217 - 3222
  • [9] A one-pot two-step microwave-assisted synthesis of N1-substituted 5,6-ring-fused 2-pyridones
    Radi, Marco
    Vallerini, Gian Paolo
    Petrelli, Alessia
    Vincetti, Paolo
    Costantino, Gabriele
    TETRAHEDRON LETTERS, 2013, 54 (50) : 6905 - 6908
  • [10] One-Pot Synthesis of Pyrimido[1,6-a]indol-1(2H)-one Derivatives by a Nucleophilic Addition/Cu-Catalyzed N-Arylation/Pd-Catalyzed C-H Activation Sequential Process
    Wang, Zhi-Jing
    Yang, Jian-Guo
    Yang, Fan
    Bao, Weiliang
    ORGANIC LETTERS, 2010, 12 (13) : 3034 - 3037
12345