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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (02): 260-265. 上一篇    下一篇

研究论文

3-芳基-6-甲基-1,6-二氢-1,2,4,5-四嗪及其衍生物的合成和晶体结构

徐峰*,1，杨珍珍1，胡惟孝2，奚立民1   

  1. (1台州职业技术学院生物与化学工程系 台州 318000)
    (2浙江工业大学药学院 杭州 310032)
  • 收稿日期:2009-04-29 修回日期:2009-07-07 发布日期:2010-02-20
  • 通讯作者: 徐峰 E-mail:xufeng901@126.com
  • 基金资助:

    国家级.国家自然科学基金

Synthesis and Structures of 3-Aryl-6-methyl-1,6-dihydro- 1,2,4,5-tetrazines and Their Derivatives

Xu Feng*,1 Yang Zhenzhen1 Hu Weixiao2 Xi Limin1   

  1. (1 Department of Biological & Chemical Engineering, Taizhou Vocational & Technical College, Taizhou 318000)
    (2 College of Pharmaceutical Science, Zhejiang University of Technol-ogy, Hangzhou 310032)
  • Received:2009-04-29 Revised:2009-07-07 Published:2010-02-20
  • Contact: Feng Xu E-mail:xufeng901@126.com

PDF

1659

被引次数

9 | 4

以乙腈和芳基腈为原料, 经过醚化、环化和还原三步方便且有效地合成了3-芳基-6-甲基-1,6-二氢-1,2,4,5-四嗪, 并在此基础上合成了一系列新的3-芳基-6-甲基-1,6-二氢-1,2,4,5-四嗪衍生物, 通过元素分析, 1H NMR, IR和HRMS对这些化合物进行了表征. 对化合物N-邻甲基苯-3-苯基-6-甲基-1,6-二氢-1,2,4,5-四嗪-1-甲酰胺(5a)的X射线晶体衍射研究表明: 其属于单斜晶系, P21 /c空间群, 晶胞参数a＝1.3941(6) nm, b＝0.5675(2) nm, c＝2.0614(8) nm; α＝γ＝90°, β＝102.055(6)°; V＝1.5949(11) nm3, 此类化合物的四嗪环采用不对称船式结构, 且具有同芳香性.

关键词: 1,6-二氢-1,2,4,5-四嗪, 不对称, 晶体结构, 同芳香性

A convenient and effective method was developed from the starting materials acetonitrile and aryl nitrile via three steps to synthesize 3-aryl-6-methyl-1,6-dihydro-1,2,4,5-tetrazines. On the basis of which, some 3-aryl-6-methyl-1,6-dihydro-1,2,4,5-tetrazine derivatives were synthesized and characterized by elemental analysis, 1H NMR, IR and HRMS techniques. The X-ray single crystal diffraction study of 6-methyl-3-phenyl-N-(2-tolyl)-1,6-dihydro-1,2,4,5-tetrazine-1-carboxamide (5a) indicates that 5a belongs to a monoclinic system, with a＝1.3941(6) nm, b＝0.5675(2) nm, c＝2.0614(8) nm; α＝γ＝90°, β＝102.055(6)°; V＝1.5949(11) nm3. The central tetrazine ring adopts an unsymmetrical boat structure. It could be considered that the molecule had a homoaromaticity.

Key words: 1,6-dihydro-1,2,4,5-tetrazine, unsymmetry, crystal structure, homoaromaticity