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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (9): 1129-1132. 上一篇    下一篇

研究简报

含2-苯基-1,2,3-三唑基单环β-内酰胺类化合物的合成

阎琴1，邵玲2，刘方明*,1,3，解正峰1，孙万赋1，李锋1   

  1. (1新疆大学化学系 乌鲁木齐 830046)
    (2南开大学元素有机化学研究所 天津 300071)
    (3杭州师范学院化学系 杭州 310012)
  • 收稿日期:2004-01-13 修回日期:2004-04-01 发布日期:2005-08-24
  • 通讯作者: 刘方明

Synthesis of Some New Monocyclic β-Lactams Containing 2-Phenyl-1,2,3-triazolyl

YAN Qin1,SHAO Ling2,LIU Fang-Ming*,1,3 XIE Zheng-Feng1
SUN Wan-Fu1,LI Feng1   

  1. (1 Department of Chemistry, Xinjiang University, Urumqi 830046)
    (2 Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071)
    (3 Department of Chemistry, Hangzhou Teacher’s Col-lege, Hangzhou 310012)
  • Received:2004-01-13 Revised:2004-04-01 Published:2005-08-24
  • Contact: LIU Fang-Ming

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寻找能口服、广谱的单环β-内酰胺类抗生素已经发展成为一个重要研究领域, 烯酮-亚胺环加成是最有效的合成方法之一. 在三乙胺与含2-苯基-1,2,3-三唑基的Schiff碱的苯溶液中逐滴加入邻苯二甲酰亚氨基乙酰氯或丙酰氯的苯溶液, 加热回流, 通过环加成反应得到含有2-苯基-1,2,3-三唑基和邻苯二甲酰亚胺基的单环β-内酰胺类化合物. 产物均为反式构型, 其结构由元素分析, IR, 1H NMR, MS以及NOESY谱得到确证.

关键词: 2-苯基-1,2,3-三唑基, 单环β-内酰胺, 环加成

Ketene-imine cycloaddition is an efficient synthetic method for monocyclic β-lactams. Under heat and reflux in benzene, a solution of the phthaloylglycyl chloride was added to a solution of triethylamine and Schiff base containing 2-phenyl-1,2,3-triazolyl. The configurations of new monocyclic β-lactams are all-trans. The structure and configuration of the compounds were confirmed by elemental analysis, IR, 1H NMR, MS and NOESY data.

Key words: 2-phenyl-1,2,3-triazolyl, cycloaddition, monocyclic β-lactam