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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (05): 670-673. 上一篇    下一篇

研究简报

系列新型硫杂杯[4]芳烃氮杂衍生物的合成

杨发福*，赵夏，杨娥，郭红玉，黄翠玉   

  1. (福建师范大学化学与材料学院 福州 350007)
  • 收稿日期:2006-09-21 修回日期:2006-09-28 发布日期:2007-05-10
  • 通讯作者: 杨发福

Syntheses of Novel Thiacalix[4]arene Aza Derivatives

YANG Fa-Fu*, ZHAO Xia, YANG E GUO Hong-Yu HUANG Cui-Yu   

  1. (College of Chemistry and Materials, Fujian Normal University, Fuzhou 350007)
  • Received:2006-09-21 Revised:2006-09-28 Published:2007-05-10
  • Contact: YANG Fa-Fu

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791

被引次数

17

在对叔丁基硫杂杯[4]芳烃的下缘1,3位引入芳醛基, 合成了硫杂杯[4]二醛基衍生物2. 化合物2与苯胺、水杨酰肼、烟酰肼、异烟酰肼等通过席夫碱缩合反应得到新型硫杂杯[4]氮杂衍生物3a～3d, 产率分别为83%, 80%, 77%和79%. 化合物2与邻苯二胺、乙二酰肼、丙二酰肼、己二酰肼等通过“1＋1”分子间缩合得到新型1,3-桥联硫杂杯[4]氮杂衍生物4a～4d, 产率53%, 51%, 59%和66%. 新化合物的结构经IR, 1H NMR, MS和元素分析等证实.

关键词: 酰肼, 席夫碱, 合成, 硫杂杯[4]芳烃

Thiacalix[4]arene bi-benzaldehyde derivative 2 was synthesized by introducing benzaldehyde groups on 1,3-position of p-tert-butylthiacalix[4]arene. Reacting compound 2 with aniline, salicylic hydrazide, nicotinic hydrazide or isonicotinic hydrazide gave series of novel thiacalix[4]arene aza derivatives 3a～3d by the Schiff-base condensation in the yields of 83%, 80%, 77% and 79%, respectively. Treatment compound 2 with o-phenylendiamine, oxalyl dihydrazide, malonic dihydrazide and adipic dihydrazide afforded novel bridged thiacalix[4]arene aza derivatives 4a～4d by “1＋1” condensation in the yields of 53%, 51%, 59% and 66%. The structures of all new compounds were characterized by IR, ESI-MS, 1H NMR spectra and elemental analyses.

Key words: hydrazide, Schiff-base, synthesis, thiacalix[4]arene