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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (10): 1502-1507. 上一篇    下一篇

研究论文

4,5-二氢-1,4-二芳基-3-乙氧羰基-5-(2-苯基-1,2,3-三唑(基)羰基)吡唑的合成和表征

吴晓龙1，叶嘉炜1，杨德保2，刘方明*,1,2   

  1. (1新疆大学化学化工学院 乌鲁木齐 830046)
    (2杭州师范大学材料与化学化工学院 杭州 310036)
  • 收稿日期:2009-11-05 修回日期:2010-01-22 发布日期:2010-05-25
  • 通讯作者: 刘方明 E-mail:fmliu859@sohu.com；
  • 基金资助:

    国家自然科学基金

Synthesis and Characterization of 1,4-Diaryl-3-ethoxycarbonyl-5- (2-phenyl-1,2,3-triazoloylcarbonyl)-4,5-dihydropyrazole Derivatives

Wu Xiaolong1 Ye Jiawei1 Yang Debao2 Liu Fangming*,1,2   

  1. (1 College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046)
    (2 College of Materials and Chemical Engineering, Hangzhou Normal Univer-sity, Hangzhou 310036)
  • Received:2009-11-05 Revised:2010-01-22 Published:2010-05-25

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被引次数

7 | 1

以2-苯基-1,2,3-三唑甲酸为原料, 通过三步反应得到关键中间体4-乙酰基-2-苯基-1,2,3-三唑(1), 再与芳醛经羟醛缩合制得相应查尔酮2a～2e, 最后与(芳基肼基)氯次甲基碳酸乙酯(3a, 3b)在三乙胺作用下, 经[3＋2] 1,3-偶极环加成反应, 生成10种未见报道的新化合物4a～4j, 其结构经IR, 1H NMR 和MS及元素分析确证. 利用单晶X射线衍射法测定了化合物4i的晶体结构.

关键词: 合成, 查尔酮, 1,2,3-三唑, 4,5-二氢吡唑, 晶体结构

4-Acetyl-2-phenyl-1,2,3-triazole (1) was synthesized from 2-phenyl-1,2,3-triazolocarboxylic acid and used as stating material for preparation of substituted chalcones 2a～2e. These chalcones were converted into corresponding 4,5-dihydropyrazole derivatives 4a～4j through [3＋2] 1,3-dipolar cycloaddition with nitrileimines, generated in situ from hydrazonyl halides (3a, 3b) in the presence of Et3N. The structures of these compounds were characterized by IR, 1H NMR, mass spectra, and elemental analysis. The structure of 4i was comfirmed by X-ray diffraction analysis.

Key words: synthesis; chalcone, 1,2,3-triazole, 4,5-dihydropyrazole, crystallographic structure