Efficient syntheses of 1,3-unsubstituted 1H-pyrazolo[3,4-b]quinolines

被引：13
|
作者：
Afghan, Arash
Baradarani, M. Mehdi [1 ]
Joule, John A. [2 ]
机构：
[1] Univ Urmia, Fac Sci, Dept Chem, Orumiyeh 57153165, Iran
[2] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
来源：
ARKIVOC | 2009年
关键词：
1H-Pyrazolo[3,4-b]quinolines; 2-chloro-3-formylquinolines; hydrazine; ethylene acetal; ethylene thioacetal; FRIEDLANDER CONDENSATION; ANTIMICROBIAL ACTIVITY; SPECTRAL PROPERTIES; FUSED PYRIDINES; DERIVATIVES; QUINOLINES; PYRAZOLOQUINOLINE; VERSATILE;
D O I：
10.3998/ark.5550190.0010.203
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of pyrazolo[3,4-b]quinolines from 2-chloro-3-formylquinolines is described. Direct reaction of the chloro-aldehydes with hydrazine was unsuccessful, but a very efficient sequence was developed in which protection of the aldehyde group was followed by displacement of the halogen by hydrazine, release of the aldehyde then leading to spontaneous ring closure giving the tricycles. The products were obtained in excellent yields.
引用
收藏
页码：20 / 30
页数：11
相关论文
共 50 条
  • [1] 1H-pyrazolo[3,4-b]quinolines and their performance in electroluminescent devices
    Funaki, J
    Imai, K
    Araki, K
    Danel, A
    Tomasik, P
    [J]. POLISH JOURNAL OF CHEMISTRY, 2004, 78 (06) : 843 - 850
  • [2] Photophysical properties of derivatives of 1H-pyrazolo[3,4-b]quinoline and 1H-pyrazolo[3,4-b]quinoxaline
    Mac, M.
    Uchacz, T.
    Andrzejak, M.
    Dane, A.
    Szlachcic, P.
    Nowak, P.
    [J]. POLISH JOURNAL OF CHEMISTRY, 2007, 81 (04) : 557 - 572
  • [3] 1H-PYRAZOLO[3,4-B] PYRIDINES
    HOHN, H
    JANSSEN, W
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1972, 9 (02) : 235 - &
  • [4] 1H-PYRAZOLO[3,4-B]PYRIDINES
    SNYDER, HR
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (06) : 1303 - 1304
  • [5] A NOVEL SYNTHESIS OF 3-SUBSTITUTED 1H-PYRAZOLO[3,4-B]QUINOLINES
    BHAT, B
    BHADURI, AP
    [J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1982, 21 (08): : 729 - 731
  • [6] 1H-pyrazolo[3,4-b]quinoline and 1H-pyrazolo[3,4-b]quinoxaline derivatives as promising materials for optoelectronic applications
    Danel, Andrzej
    Gondek, Ewa
    Kityk, Iwan
    [J]. OPTICAL MATERIALS, 2009, 32 (02) : 267 - 273
  • [7] SYNTHESIS OF 1H-PYRAZOLO[3,4-B]PYRIDINE
    HATT, TLP
    VASS, JDR
    [J]. CHEMICAL COMMUNICATIONS, 1966, (10) : 293 - &
  • [8] SULFONATION OF 1H-PYRAZOLO(3,4-B)QUINOXALINES
    KOHLSTOC.B
    HENSEKE, G
    [J]. ZEITSCHRIFT FUR CHEMIE, 1973, 13 (03): : 100 - 101
  • [9] NITRATION OF 1H-PYRAZOLO(3,4-B)QUINOXALINE
    KOHLSTOCK, B
    HENSEKE, G
    [J]. ZEITSCHRIFT FUR CHEMIE, 1972, 12 (10): : 385 - +
  • [10] Novel Bisphosphonates Derived from 1H-Indazole, 1H-Pyrazolo[3,4-b]Pyridine, and 1H-Pyrazolo[3,4-b]Quinoline
    Teixeira, Fatima C.
    Lucas, Carla
    Curto, M. Joao M.
    Teixeira, Antonio P. S.
    Duarte, M. Teresa
    Andre, Vania
    [J]. HETEROATOM CHEMISTRY, 2016, 27 (01) : 3 - 11
12345