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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (12): 1570-1574. 上一篇    下一篇

研究论文

水介质中2-氨基-4-芳基-7,7-二甲基-5-氧代-4H-5,6,7,8-四氢苯并[b]吡喃-3-羧酸酯的有效合成

史达清*，张姝，庄启亚   

  1. (1徐州师范大学化学系 徐州 221116)
    (2江苏省药用植物生物技术重点实验室 徐州 221116)
  • 收稿日期:2005-03-08 修回日期:2005-06-29 发布日期:2005-11-30
  • 通讯作者: 史达清

Efficient Synthesis of 2-Amino-4-aryl-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran-3-carboxylate in Aqueous Media

SHI Da-Qing*, ZHANG Shu, ZHUANG Qi-Ya   

  1. (1 Department of Chemistry, Xuzhou Normal University, Xuzhou 221116)
    (2 Key Laboratory of Biotechnology on Medical Plants of Jiangsu Province, Xuzhou 221116)
  • Received:2005-03-08 Revised:2005-06-29 Published:2005-11-30
  • Contact: SHI Da-Qing

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水介质中在三乙基苄基氯化铵(TEBA)存在下, 芳亚甲基氰乙酸酯与5,5-二甲基-1,3-环己二酮反应为2-氨基-4-芳基-7,7-二甲基-5-氧代-4H-5,6,7,8-四氢苯并[b]吡喃-3-羧酸酯提供了一种快速、方便、高效和洁净的合成方法. 产物的结构通过红外光谱、核磁共振氢谱、元素分析和单晶X射线衍射确定.

关键词: 苯并[b]吡喃-3-羧酸酯, 水介质, 绿色合成

In aqueous media the reaction of arylmethylene cyanoacetate with 5,5-dimethyl-1,3-cyclohexandione in the presence of triethylbenzylammonium chloride (TEBA) provides a fast, efficient, high-yielding and clean access to 2-amino-4-aryl-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran- 3-carboxylate. The structures of all compounds obtained were characterized by IR, 1H NMR spectra, elemental analysis and single crystal X-ray diffractometry.

Key words: aqueous media, green synthesis, benzo[b]pyran-3-carboxylate