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.pdfVIP

2010 年第 30 卷 有 机 化 学 Vol. 30, 2010 第 1 期, 85～91 Chinese Journal of Organic Chemistry No. 1, 85～91 ·研究论文· 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 肖琳霞 石德清* (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) 摘要 用串联的氮 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 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 Wittig 反应; 除草活性 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* (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]pyrimidin-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 ali- phatic 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 ac- tivity against Brassica campestris L at the dosage of 100 mg/L. Keywords substituted pyridi