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有机化学 ›› 2008, Vol. 28 ›› Issue (04): 680-684. 上一篇    下一篇

研究论文

2-取代氨基-6-甲基-5-氧代-4-正丁基-4,5-二氢-1,2,4-三氮唑并[1,5-a]嘧啶类衍生物的合成

张欢欢，胡秀琴*，陈永飞，刘东，许鹏飞*   

  1. (兰州大学化学化工学院 功能有机分子化学国家重点实验室 兰州 730000)
  • 收稿日期:2007-03-16 修回日期:2007-09-23 发布日期:2008-04-17
  • 通讯作者: 许鹏飞

Synthesis of 2-(Substituted amino)-4-n-butyl-6-methyl-5-oxo-4,5-dihy-dro-1,2,4-triazolo[1,5-a]pyrimidine Derivatives

ZHANG Huan-Huan,HU Xiu-Qin*,CHEN Yong-Fei,LIU Dong,XU Peng-Fei*   

  1. (State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000)
  • Received:2007-03-16 Revised:2007-09-23 Published:2008-04-17
  • Contact: XU Peng-Fei

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以2-溴丙酸甲酯、α,α-二氯甲基甲醚和胍唑为原料, 经缩合以及环化反应制得2-氨基-6-甲基-5-氧代-4,5-二氢-1,2,4-三氮唑并[1,5-a]嘧啶. 为了提高其在有机溶剂中的溶解性, 该化合物再同1-溴丁烷发生亲核取代反应得到了2-氨基-6-甲基-5-氧代-4-正丁基-4,5-二氢-1,2,4-三氮唑并[1,5-a]嘧啶, 然后与芳基醛和叔丁基异氰发生Ugi多组分反应, 合成了一系列具有潜在催吐活性的2-取代氨基-6-甲基-5-氧代-4-正丁基-4,5-二氢-1,2,4-三氮唑并[1,5-a]嘧啶类衍生物, 产品结构经质谱、核磁共振谱及元素分析确认.

关键词: 1,2,4-三氮唑并[1,5-a]嘧啶, 亲核取代, Ugi多组分反应

2-Amino-6-methyl-5-oxo-4,5-dihydro-1,2,4-triazolo[1,5-a]pyrimidine was synthesized from 2-bromopropionic acid methyl ester, α,α-dichloromethyl methyl ether and guanazole via condensation and cyclization reactions. An attempt to improve its solubility in organic solvents was achieved by the nucleophilic substitution with 1-bromobutane to give 2-amino-4-n-butyl-6-methyl-5-oxo-4,5-dihydro-1,2,4-triazolo [1,5-a]pyrimidine in a good yield. Finally, a series of 2-(substituted amino)-4-n-butyl-6-methyl-5-oxo-4,5- dihy-dro-1,2,4-triazolo[1,5-a]pyrimidines having potential emetic activity were obtained by Ugi multi-component reactions. The structures of these compounds were confirmed by MS, 1H NMR and 13C NMR spectra and elemental analysis.

Key words: nucleophilic substitution, 1,2,4-triazolo[1,5-a]pyrimidine, Ugi multi-component reaction