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化学学报
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化学学报 ›› 2005, Vol. 63 ›› Issue (9): 855-860. 上一篇    下一篇

研究论文

2-甲硫基-7(5)-取代-3-吡唑并[1,5-a]嘧啶甲酸乙酯的区域选择性合成与2D NMR 研究

李明*1 2，郭维斯1，文丽荣1，钟惠民1，杨华铮2   

  1. (1青岛科技大学化学与分子工程学院 青岛 266042)
    (2南开大学元素有机化学国家重点实验室 天津 300071)
  • 投稿日期:2004-08-12 修回日期:2005-01-04 发布日期:2010-12-10
  • 通讯作者: 李明

Regioselective Synthesis and 2D NMR Research of Ethyl 2-Methyl-thio-7(5)-substituted Pyrazolo[1,5-a]pyrimidine-3-carboxylate

LI Ming*1,2, GUO Wei-Si1, WEN Li-Rong1, ZHONG Hui-Min1, YANG Hua-Zheng2   

  1. (1 College of Chemical and Molecular Technology, Qingdao University of Science and Technology, Qingdao 266042)
    (2 State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071)
  • Received:2004-08-12 Revised:2005-01-04 Published:2010-12-10
  • Contact: LI Ming

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利用3-甲硫基-4-乙氧羰基-5-氨基-1H-吡唑分别与甲基/芳基烯胺酮反应, 合成了8种新的化合物2-甲硫基-7-取代-3-吡唑并[1,5-a]嘧啶甲酸乙酯(3a～3g)和2-甲硫基-5-甲基-3-吡唑并[1,5-a]嘧啶甲酸乙酯(4a). 化合物的结构均经元素分析, IR, 1H NMR, MS所证实, 异构体3a和4a的结构进一步由13C NMR, HMQC和HMBC确认. 同时, 探讨了区域选择性合成吡唑并[1,5-a]嘧啶类化合物可能的反应机理, 并对部分化合物杀菌活性进行了测试.

关键词: 吡唑并[1,5-a]嘧啶, 二维核磁, 反应机理, 区域选择性, 合成

By the reaction of 3-methylthio-4-ethoxycarbonyl-5-amino-1H-pyrazole with substituted enaminones, eight new compounds of ethyl 2-methylthio-7-substituted pyrazolo[1,5-a]pyrimidine-3-carboxylate (3a～3g) and ethyl 2-methylthio-5-methyl pyrazolo[1,5-a]pyrimidine-3-carboxylate (4a) have been synthesized respectively. The structures of all compounds were characterized by elemental analyses, IR, 1H NMR, and MS. Structures of regioisomer 3a and 4a were further determined by 13C NMR, HMQC and HMBC. In the meantime, the plausible mechanism for regioselective synthesis of pyrazolo[1,5-a]pyrimidine was discussed. The preliminary test showed that some of the compounds had somewhat antifungal activities.

Key words: pyrazolo[1,5-a]pyrimidine, 2D NMR, reaction mechanism, regioselectivity, synthesis