Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (06): 744-748. Previous Articles     Next Articles

Original Articles

N-糖基-N'-酰氨基硫脲及其环合产物的合成

田添a,曹玲华*,a,b,钱兆生a   

  1. (a新疆大学化学化工学院 乌鲁木齐 830046)
    (b南开大学元素有机化学国家重点实验室 天津 300071)
  • 收稿日期:2006-08-22 修回日期:2006-10-17 发布日期:2007-05-21
  • 通讯作者: 曹玲华

Synthesis of N-Glycosyl-N'-amido Thioureas and Their RelatedHeterocyclic Compounds

TIAN Tiana, CAO Ling-Hua*,a,b, QIAN Zhao-Shenga   

  1. (a College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046)
    (b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071)
  • Received:2006-08-22 Revised:2006-10-17 Published:2007-05-21
  • Contact: CAO Ling-Hua

The starting material L-α-amino acids were converted into N-p-toluenesulfonyl-L-α-amino acid hydrazides 2 through following steps, esterification, amino protection and hydrazinolysis. The reaction of 2 with glycosyl isothio-cyanates 35 gave the novel compounds, N-glycosyl-N'-amido thioureas 68. The compounds 68 were cyclized under the system of Hg(OAc)2/EtOH to afford a series of new compounds, 2- p-toluenesulfonylaminoalkyl-5-glycosylamino-1,3,4-oxadiazoles 911. The structures of the new compounds were confirmed by IR, 1H NMR, MS spectra and elemental analysis.

Key words: amino acid hydrazide, 1,3,4-oxadiazole, glycosyl isothiocyanate, amido thiourea, L-α-amino acid