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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (03): 364-367. 上一篇    下一篇

研究简报

离子液体中6-(2,3-环氧丙氧基)-2(1H)-喹啉酮及其衍生物的合成

裴文*， 邓琼，王海滨，孙莉   

  1. (浙江工业大学化学工程与材料学院 杭州 310014)
  • 收稿日期:2005-05-29 修回日期:2005-09-05 发布日期:2006-02-28
  • 通讯作者: 裴文

Synthesis of 6-(2,3-Epoxypropoxy)-1,2-dihydroquinolin-2(1H)-one and Its Derivatives in Ionic Liquids

PEI Wen*,DENG Qiong,WANG Hai-Bin,SUN Li   

  1. (College of Chemical Engineering and Materials, Zhejiang University of Technology, Hangzhou 310014)
  • Received:2005-05-29 Revised:2005-09-05 Published:2006-02-28
  • Contact: PEI Wen

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6-(3-氨基-2-羟基丙基)-2-(1H)-喹啉酮衍生物被发现具有新的正性肌力的活性. 设计合成了一系列新的氨丙醇类喹啉酮化合物. 首先研究了6-羟基-2-(1H)-喹啉酮环氧化物2在离子液体中的合成, 该反应后处理简便, 收率高, 对环境友好. 然后用合成得到的2-(1H)-喹啉酮环氧化合物在离子液体中与一系列具有生物活性的有机碱反应, 合成了氨丙醇类2-(1H)-喹啉酮化合物3. 然后由6-羟基-2-(1H)-喹啉酮出发, 在离子液体中, 进行了一锅法合成氨丙醇类2-(1H)-喹啉酮化合物的研究. 制得的2b, 3b～3f 6个新化合物用IR, 1H NMR, MS和元素分析进行了结构表征.

关键词: 合成, 2-(1H)-喹啉酮, 正性肌力活性, 离子液体, 环氧化合物, 氨丙醇

6-(3-Amino-2-hydroxylpropyl)-1,2-dihydroquinolin-2(1H)-ones are important intermediates of cardiovascular drugs. Epoxypropoxy 1,2-dihydroquinolin-2(1H)-one derivatives 2 were synthesized by the reaction of 6-hydroxy-1,2-dihydroquinolin-2(1H)-one or 4-methyl-6-hydroxy-1,2-dihydroquinolin-2(1H)- one with epoxy chloropropane in ionic liquid. The new procedure for preparing 2 has the advantages of good yield, simplified operation and environ-mental benignity. Then the new 1,2-dihydroquinolin-2(1H)-one aminopropanol compound 3 was synthesized by the reaction of the epoxypropoxy 1,2-dihydroquinolin-2(1H)-one compound with organic base compounds with biological activity. One pot synthesis of the aminopropanol compounds were studied from 6-hydroxy-1,2-dihydroquinolin-2(1H)-one or 4-methyl- 6-hydroxy-1,2-dihydroquinolin-2(1H)-one in ionic liquid. The structures of the six new com-pounds (2b, 3b～3f ) were characterized by IR, 1H NMR, MS spectra and elemental analyses.

Key words: synthesis, ionic liquid, positive inotropic activity, epoxy compound, aminopropanol, 1,2-dihydroquinolin-2-one