Facile and efficient synthesis of pyrazoloisoquinoline and pyrazolopyridine derivatives using recoverable carbonaceous material as solid acid catalyst

被引:32
作者
Chen, Zhu [1 ]
Shi, Yingxia [1 ]
Shen, Qingqing [1 ]
Xu, Haixia [1 ]
Zhang, Furen [1 ]
机构
[1] Shaoxing Univ, Zhejiang Key Lab Alternat Technol Fine Chem Proc, Shaoxing 312000, Zhejiang, Peoples R China
关键词
Synthesis; Pyrazoloisoquinolines; Pyrazolopyridines; Recyclability; Multi-component reaction; REGIOSELECTIVE SYNTHESIS; WATER; INHIBITORS; CHEMISTRY; BIODIESEL; POTENT;
D O I
10.1016/j.tetlet.2015.06.044
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient procedure for the synthesis of pyrazoloisoquinoline and pyrazolopyridine derivatives by one-pot three-component condensation of aminopyrazoles, aldehydes, and cycloketones in water using carbonaceous material as solid acid catalyst is described. The procedure offers several advantages such as simple experimental and work-up procedures, high yield, recovery, and reusability of metal-free solid acid heterogeneous catalyst along with tolerance of a wide range of functional groups. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4749 / 4752
页数:4
相关论文
共 37 条
  • [11] Solvent-free multicomponent reactions using the novel N-sulfonic acid modified poly(styrene-maleic anhydride) as a solid acid catalyst
    Heravi, Majid. M.
    Hashemi, Elaheh
    Beheshtiha, Yahya Shirazi
    Kamjou, Khadijeh
    Toolabi, Maryam
    Hosseintash, Nastaran
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 392 : 173 - 180
  • [12] Superior storage performance of a Si@SiOx/C nanocomposite as anode material for lithium-ion batteries
    Hu, Yong-Sheng
    Demir-Cakan, Rezan
    Titirici, Maria-Magdalena
    Mueller, Jens-Oliver
    Schloegl, Robert
    Antonietti, Markus
    Maier, Joachim
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) : 1645 - 1649
  • [13] Facile Three-Component Synthesis of Macrocyclane-Fused Pyrazolo[3,4-b] pyridine Derivatives
    Jiang, Bo
    Liu, Yin-Ping
    Tu, Shu-Jiang
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (16) : 3026 - 3035
  • [14] Synthesis of tetrahydro-4H-indol-4-one derivatives catalyzed by carbonaceous material
    Li, Chunmei
    Liang, Xuezheng
    Zhang, Furen
    Qi, Chenze
    [J]. CATALYSIS COMMUNICATIONS, 2015, 62 : 6 - 9
  • [15] A green approach for the synthesis of long chain aliphatic acid esters at room temperature
    Li, Xinzhong
    Eli, Wumanjiang
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2008, 279 (02) : 159 - 164
  • [16] One-step synthesis of carbon functionalized with sulfonic acid groups using hydrothermal carbonization
    Liang, Xuezheng
    Zeng, Minfeng
    Qi, Chenze
    [J]. CARBON, 2010, 48 (06) : 1844 - 1848
  • [17] PYRAZOLO[3,4-B]PYRIDINES - SYNTHESES, REACTIONS, AND NUCLEAR MAGNETIC-RESONANCE SPECTRA
    LYNCH, BM
    KHAN, MA
    TEO, HC
    PEDROTTI, F
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (03): : 420 - 428
  • [18] Selective partial hydrogenation of hydroxy aromatic derivatives with palladium nanoparticles supported on hydrophilic carbon
    Makowski, Philippe
    Cakan, Rezan Demir
    Antonietti, Markus
    Goettmann, Frederic
    Titirici, Maria-Magdalena
    [J]. CHEMICAL COMMUNICATIONS, 2008, (08) : 999 - 1001
  • [19] Water-mediated one-pot synthetic route for pyrazolo[3,4-b]quinolines
    Mali, Jyotirling R.
    Pratap, Umesh R.
    Jawale, Dhanaji V.
    Mane, Ramrao A.
    [J]. TETRAHEDRON LETTERS, 2010, 51 (30) : 3980 - 3982
  • [20] Synthesis and 3D QSAR of new pyrazolo[3,4-b]pyridines:: Potent and selective inhibitors of A1 adenosine receptors
    Manetti, F
    Schenone, S
    Bondavalli, F
    Brullo, C
    Bruno, O
    Ranise, A
    Mosti, L
    Menozzi, G
    Fossa, P
    Trincavelli, ML
    Martini, C
    Martinelli, A
    Tintori, C
    Botta, M
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (23) : 7172 - 7185