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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (02): 238-243. 上一篇    下一篇

研究论文

N-[2-(1H-吲哚-3)乙基]-2-乙酰噻唑-4-甲酰胺及其类似物的合成

李多，杨海申，谢龙观，徐效华*   

  1. (南开大学元素有机化学研究所元素有机化学国家重点实验室 天津 300071)
  • 收稿日期:2009-05-25 修回日期:2009-08-20 发布日期:2010-02-20
  • 通讯作者: 李多 E-mail:liduowjq@gmail.com
  • 基金资助:

    国家级.国家自然科学基金

Synthesis of N-[2-(1H-Indol-3-yl)ethyl]-2-acetylthiazole- 4-caboxamide and Its Analogues

Li Duo Yang Haishen Xie Longguan Xu Xiaohua*   

  1. (State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071)
  • Received:2009-05-25 Revised:2009-08-20 Published:2010-02-20
  • Contact: Li Duo E-mail:liduowjq@gmail.com

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N-[2-(1H-吲哚-3)乙基]-2-乙酰噻唑-4-甲酰胺是最近从海洋细菌中分离得到的一种新型的天然杀藻剂, 以D-丙氨酸为原料合成了该化合物, 并用类似的方法首次合成了它的类似物2, 3和4. 其关键步骤为通过将取代的4-噻唑甲酸制成混酐与色胺连接的偶联反应. 各中间体都通过1H NMR和13C NMR得到证实. 最终产品通过1H NMR, 13C NMR和HRMS证实, 与文献所报道相一致.

关键词: 天然化合物, 天然杀藻剂, 丙氨酸, 噻唑, 混酐, 色胺

The synthesis of N-(2-(1H-indol-3-yl)ethyl)-2-acetylthiazole-4-carboxamide (1), which is a new algaecide from the marine bacterium, was achieved effectively from D-alanine. Its analogues 2, 3 and 4 were firstly synthesized using the similar approach. The key step was a coupling reaction via the mixed anhydride. All structures were confirmed by 1H NMR and 13C NMR spectra. The final compounds were confirmed by 1H NMR, 13C NMR and HRMS techniques, and the results are consistent with the reported natural prod-ucts.

Key words: natural product, natural algaecide, alanine, thiazole, mixed anhydride, tryptamide