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利用串联的氮杂Wittig反应方便合成3-[取代吡啶(噻唑)甲基]-1,2,3-三唑[4,5-d]嘧啶-7-酮及其除草活性
引用本文:肖琳霞,石德清. 利用串联的氮杂Wittig反应方便合成3-[取代吡啶(噻唑)甲基]-1,2,3-三唑[4,5-d]嘧啶-7-酮及其除草活性[J]. 有机化学, 2010, 30(1): 85-91
作者姓名:肖琳霞  石德清
作者单位:华中师范大学化学学院,农药与化学生物学教育部重点实验室,武汉,430079
基金项目:国家自然科学基金,湖北自然科学基金 
摘    要:
用串联的氮杂Wittig关环反应合成了一系列3-[取代吡啶(嘧啶)甲基]-1,2,3-三唑[4,5-d]嘧啶-7-酮.膦亚胺4和芳基异氰酸酯发生氮杂Wittig反应生成碳二亚胺5,继而在乙醇钠催化下与各种脂肪伯胺关环,以较好的收率得到目标产物7.初步生物活性测试结果表明:该系列部分化合物在100 mg/L的浓度下对双子叶植物油菜显示出较好的除草活性.

关 键 词:取代吡啶  噻唑  1,2,3-三唑[4,5-d]嘧啶-7-酮  氮杂Wittig反应  除草活性
收稿时间:2009-05-09
修稿时间:2009-07-06

A Convenient Synthesis of 3-[Substituted pyridyl(or thiazolyl)methyl]-1,2,3-triazolo[4,5-d]pyrimidin-7-one via the Tandem Aza-Wittig Reaction and Their Herbicidal Activity
Xiao Linxia,Shi Deqing. A Convenient Synthesis of 3-[Substituted pyridyl(or thiazolyl)methyl]-1,2,3-triazolo[4,5-d]pyrimidin-7-one via the Tandem Aza-Wittig Reaction and Their Herbicidal Activity[J]. Chinese Journal of Organic Chemistry, 2010, 30(1): 85-91
Authors:Xiao Linxia  Shi Deqing
Affiliation:(Key Laboratory of Pesticide and Chemical Biology of Ministry of Education,College of Chemistry, Central China Normal University,Wuhan 430079)
Abstract:
A series of 3-[substituted pyridyl(or thiazolyl)methyl]-1,2,3-triazolo[4,5-d]pyfimidin-7-ones were synthesized via the tandem Aza-Wittig reaction annulation.The carbodiimides 5,obtained from the aza-Wittig reaction of iminophosphorane 4 with aromatic isocyanates,reacted with a variety of primary aliphatic amines in the presence of a catalytic amount of EtONa to give the target compounds 7 in moderate yields.The preliminary bioassay indicated that some of the target compounds displayed good herbicidal activity againstBrassica campestris L at the dosage of 100 mg/L.
Keywords:substituted pyridine  thiazole  1,2,3-triazolo[4,5-d]pyrimidin-7-one  aza-Wittig reaction  herbicidal activity
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