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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (02): 269-273. 上一篇    下一篇

研究简报

2-[1-(1,2,4-三唑)甲基]-3-乙酰基-2,5-二取代芳基-1,3,4-噁二唑啉类化合物的合成

杨德保 ; 刘方明* ; 杨 春; 沈松伟;
周英雷; 徐 峰; 叶嘉炜
  

  1. (杭州师范大学材料与化学化工学院 杭州 310036)
  • 收稿日期:2008-03-24 修回日期:2008-05-30 发布日期:2009-02-20
  • 通讯作者: 刘方明

Synthesis of 3-Acetyl-2,5-di[(un)substituted phenyl]-2- (1,2,4-triazol-1-ylmethyl)-1,3,4-oxadiazoline

Yang, Debao ; Liu, Fangming*; Yang, Chun; Shen, Songwei ;
Zhou, Yinglei ; Xu, Feng ; Ye, Jiawei
  

  1. (College of Materials and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036)
  • Received:2008-03-24 Revised:2008-05-30 Published:2009-02-20
  • Contact: Liu, Fangming

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1549

被引次数

15

在冰醋酸存在下, 4-取代苯乙酮和溴素容易进行溴代反应, 得到α-溴-4-取代苯乙酮; 将其和1,2,4-三唑在丙酮中反应, 得到α-(1,2,4-三唑-1-基)-4-取代苯乙酮2; 在冰醋酸催化下, 2和4-取代苯甲酰肼1进行缩合, 得到相应酰腙衍生物3; 化合物3在乙酸酐的作用下环化生成一系列2-[1-(1,2,4-三唑)甲基]-3-乙酰基-2,5-二取代芳基-1,3,4-噁二唑啉4. 化合物4的结构经IR, 1H NMR, MS, 元素分析和单晶衍射确证.

关键词: 晶体结构, 1H-1,2,4-三唑, 1,3,4-噁二唑, 合成

In the presence of glacial acetic acid, 4-substituted acetophenone was brominated easily to afford α-bromo-4-substituted acetophenone, which was reacted with 1,2,4-triazole in acetone to get α-(1,2,4-tria-
zole-1-yl)-4-substituted acetophenone (2). Reaction of 4-substituted benzohydrazide (1) with compound 2 gave the corresponding hydrazones 3, which could be readily converted to their congener oxadiazolines 4 in good yields by treatment with acetic anhydride. Compounds 4 were confirmed by IR, 1H NMR, MS, ele-mental analysis and single crystal X-ray diffraction.

Key words: 1,3,4-oxadiazole, synthesis, crystal structure, 1H-1,2,4-triazole