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
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 33期
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
  • [1] Efficient syntheses of 1,3-unsubstituted 1H-pyrazolo[3,4-b]quinolines
    Afghan, Arash
    Baradarani, M. Mehdi
    Joule, John A.
    [J]. ARKIVOC, 2009, : 20 - 30
  • [2] Expedient Synthesis of 3-Alkoxymethyl- and 3-Aminomethyl-Pyrazolo[3,4-b]pyridines
    Beutner, Gregory L.
    Kuethe, Jeffrey T.
    Kim, Mary M.
    Yasuda, Nobuyoshi
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (02) : 789 - 794
  • [3] Towards a bio-based industry: Benign catalytic esterifications of succinic acid in the presence of water
    Budarin, Vitaly
    Luque, Rafael
    Macquarrie, Duncan J.
    Clark, James H.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (24) : 6914 - 6919
  • [4] Protic Acid Immobilized on Solid Support as an Extremely Efficient Recyclable Catalyst System for a Direct and Atom Economical Esterification of Carboxylic Acids with Alcohols
    Chakraborti, Asit K.
    Singh, Bavneet
    Chankeshwara, Sunay V.
    Patel, Alpesh R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) : 5967 - 5974
  • [5] 1,3,5-Triazine-2,4,6-triyltrisulfamic acid (TTSA): A new organic solid acid for the nitrosation of secondary amines and oxidation of urazoles in the presence of NaNO2 under mild and heterogeneous conditions
    Chehardoli, Gholamabbas
    Zolfigol, Mohammad Ali
    Faal-Rastegar, Toktam
    Mallakpour, Shadpour
    Ghorbani-Choghamarani, Arash
    [J]. JOURNAL OF CHEMICAL SCIENCES, 2009, 121 (04) : 441 - 447
  • [6] Clean, reusable and low cost heterogeneous catalyst for amide synthesis
    Comerford, James W.
    Clark, James H.
    Macquarrie, Duncan J.
    Breeden, Simon W.
    [J]. CHEMICAL COMMUNICATIONS, 2009, (18) : 2562 - 2564
  • [7] Perchloric Acid and Its Salts: Very Powerful Catalysts in Organic Chemistry
    Dalpozzo, Renato
    Bartoli, Giuseppe
    Sambri, Letizia
    Melchiorre, Paolo
    [J]. CHEMICAL REVIEWS, 2010, 110 (06) : 3501 - 3551
  • [8] Structure-activity studies for a novel series of tricyclic dihydropyridopyrazolones and dihydropyridoisoxazolones as KATP channel openers
    Drizin, I
    Altenbach, RJ
    Buckner, SA
    Whiteaker, KL
    Scott, VE
    Darbyshire, JF
    Jayanti, V
    Henry, RF
    Coghlan, MJ
    Gopalakrishnan, M
    Carroll, WA
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (08) : 1895 - 1904
  • [9] Pyrazolopyridines as a novel structural class of potent and selective PDE4 inhibitors
    Hamblin, J. Nicole
    Angell, Tony D. R.
    Ballantine, Stuart P.
    Cook, Caroline M.
    Cooper, Anthony W. J.
    Dawson, John
    Delves, Christopher J.
    Jones, Paul S.
    Lindvall, Mika
    Lucas, Fiona S.
    Mitchell, Charlotte J.
    Neu, Margarete Y.
    Ranshaw, Lisa E.
    Solanke, Yemisi E.
    Somers, Don O.
    Wiseman, Joanne O.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (14) : 4237 - 4241
  • [10] A carbon material as a strong protonic acid
    Hara, M
    Yoshida, T
    Takagaki, A
    Takata, T
    Kondo, JN
    Hayashi, S
    Domen, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (22) : 2955 - 2958
1234