高等学校化学学报

高等学校化学学报 ›› 2005, Vol. 26 ›› Issue (2): 250.

• 研究论文 • 上一篇    下一篇

3-氨基-6/8取代-1H-吡唑[4,3-c]喹啉类化合物的合成

乔仁忠1,2, 张自义3, 赵玉芬1   

  1. 1. 清华大学化学系,生命有机磷化学及化学生物学教育部重点实验室,北京 100084;
    2. 北京化工大学生命科学与生物技术学院,北京 100029;
    3. 兰州大学化学化工学院,应用有机国家重点实验室,兰州 730000
  • 收稿日期:2004-02-02 出版日期:2005-02-10 发布日期:2005-02-10
  • 通讯作者: 赵玉芬(1948年出生),女,博士,教授,博士生导师,中国科学院院士,主要从事有机化学和化学生物学领域的研究.E-mail:yfzhao@mail.tsinghua.edu.cn E-mail:yfzhao@mail.tsinghua.edu.cn
  • 基金资助:

    国家自然科学基金重点项目(批准号:20132020);博士后科学基金项目(批准号:200303)资助

Synthesis of 3-Amino-6/8-Substituted-1H-pyrazolo[4,3-c]quinolines

QIAO Ren-Zhong1,2, ZHANG Zi-Yi3, ZHAO Yu-Fen1   

  1. 1. The Key Laboratory of Bio-organic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China;
    2. College of Life Science and Biotechnology, Beijing University of Chemical Technology, Beijing 100029, China;
    3. College of Chemistry and Chemical Engineering, National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
  • Received:2004-02-02 Online:2005-02-10 Published:2005-02-10

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被引次数

43

摘要： 研究了合成3-氨基-6/8取代-1H-吡唑[4,3-c]喹啉类化合物的简易方法.通过3-芳基-4-氨基-5-巯基-1,2,4-三唑与6-/8-取代-4-羟基喹啉羧酸在三氯氧磷催化下的缩合反应及所生成的3-芳基-6-(6-/8-取代-4-氯喹啉-3-基)-1,2,4-三唑[3,4-b]-1,3,4-噻二唑类化合物与水合肼在乙醇中的肼解反应,合成了6个3-氨基-6/8取代-1H-吡唑[4,3-c]喹啉类化合物,并对活泼的氨基进行了初步研究,新化合物通过元素分析,IR,1HNMR和MS确定结构,并讨论了其波谱性质.

关键词: 1, 2, 4-三唑[3, 4-b]-1, 3, 4-噻二唑, 3-氨基-6/8取代-1H-吡唑[4, 3-c]喹啉, 合成, 性质

Abstract: A simple synthesis of 3-amino-6/8-substituted-1H-pyrazolo[4,3-c]quinolines via closed ring reaction of 4-amino-3-aryl-5-mercapto-s-1,2,4-triazoles with 1,4-dihydro-4-oxo-quinoline-3-carboxylic acids in the presence of phosphoryl chloride, followed by the ring-opening reaction in the presence of hydrazine hydrate was described. This novel and straightforward method for the construction the 3-amino-1H-pyrazolo[4,3-c]quinolines can be carried out under mild conditions by using readily accessible or commercially available inexpensive materials. The new compounds were dertemined by elementary analyses, IR, 1H NMR and MS spectra. Their spectral properities were also discussed. This mothod may represent a potentially useful route to otherwise laboriously accessible condensed pyrazoles ring systems. With the advantage of economy, a single pot procedure, excellent yields and mild conditions. This condensed pyrazoles can be synthesized on a large scale conveniently and economically.

Key words: 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazole, 3-Amino-6/8-substituted-1H-pyrazolo[4,3-c]quinoline, Synthesis, Property

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