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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (02): 228-232. 上一篇    下一篇

研究简报

水相中2-氨基-4-芳基-5,6-二氢化-4H-吡喃并[3,2-c]喹啉-5-酮衍生物的合成

王香善*,1,2,3，曾兆森1，李玉玲1,3，史达清1,3，屠树江1,3
魏贤勇2，宗志敏2   

  1. (1徐州师范大学化学系 徐州221116)
    (2中国矿业大学化学工程学院 徐州221008)
    (3江苏省药用植物生物技术重点实验室 徐州 221116)
  • 收稿日期:2005-02-23 修回日期:2005-08-05 发布日期:2006-01-21
  • 通讯作者: 王香善

Synthesis of 2-Amino-4-aryl-5,6-dihydro-4H-pyrano[3,2-c]quinolin-5-one Derivatives in Water

WANG Xiang-Shan*,1,2,3,ZENG Zhao-Sen1,3,LI Yu-Ling1,3,SHI Da-Qing1,3
TU Shu-Jiang1,3,WEI Xian-Yong2,ZONG Zhi-Min2   

  1. (1 Department of Chemistry, Xuzhou Normal University, Xuzhou 221116)
    (2 School of Chemical Engineering, China University of Mining and Tech-nology, Xuzhou 221008)
    (3 Key Laboratory of Biotechnology on Medical Plant of Jiangsu Province, Xuzhou 221116)
  • Received:2005-02-23 Revised:2005-08-05 Published:2006-01-21
  • Contact: WANG Xiang-Shan

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以芳亚甲基丙二腈或2-氰基-3-芳基丙烯酸酯和4-羟基喹啉-2-酮为原料, 水为溶剂, 在TEBA(三乙基苄基氯化铵)催化下90 ℃, 合成了2-氨基-4-芳基-5,6-二氢化-4H-吡喃[3,2-c]喹啉-5-酮衍生物. 和其它方法相比, 该反应具有反应条件温和, 产率高(87%～96%)和环境友好等优点. 产物的结构通过熔点, IR, 1H NMR和元素分析表征. 化合物3m的结构通过X单晶衍射分析确证.

关键词: 吡喃并喹啉, 水, TEBA, 合成

A series of 2-amino-4-aryl-5,6-dihydro-4H-pyrano[3,2-c]quinolin-5-one derivatives were synthesized by the TEBA (triethylbenzyl ammonium chloride) catalyzed reaction of arylmethylidenemalononitriles or 3-aryl-2-cyano-1-acrylate with 4-hydroxy-1,2-dihydroquinolin-2-one in water at 90 ℃. Compared with other synthetic methods, this method has the advantages of milder reaction conditions, high yields (87%～96%) and environmentally benign procedure. The structures of the products were characterized by melting points, IR, 1H NMR spectra and elemental analysis, and the structure of compond 3m was confirmed by X-ray diffraction analysis.

Key words: water, TEBA, synthesis, pyranoquinoline