Acta Chimica Sinica ›› 2007, Vol. 65 ›› Issue (16): 1663-1669. Previous Articles     Next Articles

Original Articles

含噻二唑官能基的对叔丁基硫桥杯[4]芳烃衍生物的合成及结构

赵邦屯*,1, 王璐2, 冶保献*,2   

  1. (1洛阳师范学院化学系 洛阳 471022)
    (2郑州大学化学系 郑州 450001)
  • 投稿日期:2007-03-28 修回日期:2007-05-25 发布日期:2007-08-28
  • 通讯作者: 赵邦屯, 冶保献

Synthesis and Structure of p-tert-Butylthiacalix[4]arene Derivatives Containing Thiadiazole Functional Moieties

ZHAO Bang-Tun*,1; WANG Lu2; YE Bao-Xian*,2   

  1. (1 Department of Chemistry, Luoyang Normal University, Luoyang 471022)
    (2 Department of Chemistry, Zhengzhou University, Zhengzhou 450001)
  • Received:2007-03-28 Revised:2007-05-25 Published:2007-08-28
  • Contact: ZHAO Bang-Tun; YE Bao-Xian

The p-tert-butylthiacalix[4]arene (1) was firstly alkylated with methyl iodide to obtain thiacalix[4]arene (2), which was reacted with 1,2-dibromoethane and 1,3-dibromopropane to give thiacalix[4]arene derivatives 3 and 4 in the presence of potassium carbonate, respectively. A series of p-tert-butylthiacalix[4]arene derivatives 5a, 5b, 6a and 6b which append 1,3,4-thiadiazol-2-ylthio groups at the lower rims were easily synthesized in good yields by the reaction of di(bromoalkoxy)calix[4]arene intermediates 3 or 4 with 2-mercapto-1,3,4-thiadiazole derivatives in the presence of sodium hydroxide. All novel compounds were characterized by 1H NMR, 13C NMR, IR, MS and elemental analysis. Meanwhile, the structures of thiacalix[4]arene derivatives 3 and 5a were identified by X-ray diffraction analysis.

Key words: thiacalix[4]arene, thiadiazole, synthesis, crystal structure