Facile Three-Component Synthesis of Macrocyclane-Fused Pyrazolo[3,4-b] pyridine Derivatives

被引：31
|
作者：
Jiang, Bo [1 ]
Liu, Yin-Ping [1 ]
Tu, Shu-Jiang [1 ]
机构：
[1] Xuzhou Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 16期
基金：
中国国家自然科学基金;
关键词：
Multicomponent reactions; Microwave reactions; Fused ring systems; Nitrogen heterocycles; Ketones; DIELS-ALDER REACTION; ASSISTED MULTICOMPONENT REACTIONS; ONE-POT; REGIOSELECTIVE SYNTHESIS; CYCLOADDITION; INHIBITORS; ACCESS;
D O I：
10.1002/ejoc.201100127
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of new functionalized macrocyclane-fused pyrazolo[ 3,4-b]pyridine derivatives with an aryl group at the 2-position of the pyridine nucleus have been synthesized by microwave-assisted three-component reactions of aldehydes, aminopyrazole and cycloketones in HOAc using 1.0 equiv. of TFA as a promoter. The procedure is facile, avoiding time-consuming and costly syntheses, tedious work-ups and purifications of precursors as well as protection/deprotection of functional groups. This method is very efficient due to short reaction times and easy work-up and provides an efficient and promising synthetic strategy for the construction of the macrocyclane-fused pyrazolo[3,4-b] pyridine skeleton.
引用
收藏
页码：3026 / 3035
页数：10
相关论文
共 50 条
  • [1] Three-component, one-pot synthesis of pyrazolo[3,4-b]pyridine derivatives in aqueous media
    Shi, Da-Qing
    Yao, Hao
    Shi, Jing-Wen
    SYNTHETIC COMMUNICATIONS, 2008, 38 (10) : 1662 - 1669
  • [2] Three-Component Synthesis of Chromeno[4,3-d]pyrazolo[3,4-b]-pyridine Derivatives and Their Fluorescence Properties
    Zhang, Mengye
    Wang, Ning
    Xu, Wentao
    Huang, Zhibin
    Shi, Daqing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (04) : 1085 - 1094
  • [3] Three-Component Synthesis of Oxazolo[3,4-b]quinoline Derivatives
    Tong, Guangjin
    Fan, Wei
    Jiang, Bo
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (12) : 2578 - 2582
  • [4] Synthesis and antimicrobial activity of pyrazolo [3,4-b] pyridine derivatives
    Patel, HD
    Mistry, BD
    Desai, KR
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 13 (02) : 177 - 178
  • [5] Alcohol Participates in the Synthesis of Functionalized Coumarin-Fused Pyrazolo[3,4-b]Pyridine from a One-Pot Three-Component Reaction
    Lin, Wei
    Zhuang, Cangwei
    Hu, Xiuxiu
    Zhang, Juanjuan
    Wang, Juxian
    MOLECULES, 2019, 24 (15):
  • [6] A one-pot three-component strategy for highly diastereoselective synthesis of spirocycloalkane fused pyrazolo[3,4-b]pyridine derivatives using recyclable solid acid as a catalyst
    Zhang, Furen
    Li, Chunmei
    Qi, Chenze
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (17) : 2456 - 2466
  • [7] An efficient domino strategy for synthesis of novel spirocycloalkane fused pyrazolo[3,4-b]pyridine derivatives
    Li, Chunmei
    Zhang, Furen
    Shen, Zhenlu
    TETRAHEDRON, 2020, 76 (52)
  • [8] Green Synthesis of Fused Polycyclic Pyrazolo[3,4-b][1,6]naphthyridine Derivatives in Ionic Liquids via Three-Component Reaction
    Feng, Bin-Bin
    Zhang, Mei-Mei
    Wang, Xiang-Shan
    POLYCYCLIC AROMATIC COMPOUNDS, 2016, 36 (04) : 478 - 489
  • [9] A NOVEL SYNTHESIS OF PYRAZOLO 3,4-B!PYRIDINE
    KHAN, MA
    LYNCH, BM
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1970, 7 (01) : 247 - &
  • [10] An Efficient Synthesis of Pyrazolo[3,4-b]pyridine Derivatives in Ionic Liquid
    Shi, Da-Qing
    Zhou, Yao
    Liu, Hai
    SYNTHETIC COMMUNICATIONS, 2010, 40 (24) : 3660 - 3668
12345