高等学校化学学报 ›› 2002, Vol. 23 ›› Issue (10): 1877.

• 研究论文 • 上一篇    下一篇

1,6-二氢-S-四嗪与异氰酸酯催化重排反应的研究

胡惟孝, 孙雅泉, 袁庆, 杨忠愚   

  1. 浙江工业大学制药工程研究所, 杭州 310014
  • 收稿日期:2001-07-31 出版日期:2002-10-24 发布日期:2002-10-24
  • 通讯作者: 胡惟孝(1941年出生),男,博士,教授,博士生导师,从事有机合成和反应研究.E-mail:huyang@mail.hz.z.jcn E-mail:huyang@mail.hz.z.jcn
  • 基金资助:

    浙江省自然科学基金(200016)资助

Catalytical Rearrangement of 1,6-Dihydro-S-tetrazine with Isocyanate

HU Wei-Xiao, SUN Ya-Quan, YUAN Qing, YANG Zhong-Yu   

  1. Institute of Pharmaceutical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
  • Received:2001-07-31 Online:2002-10-24 Published:2002-10-24

摘要: 3,6-二甲基-1,6-二氢-S-四嗪与异氰酸酯反应,在N′,N-二甲基苯胺催化下生成N-苯基-3,6-二甲基-1,6-二氢-S四嗪-1-甲酰胺,在4-二甲胺基吡啶(DMAP)催化则生成一类新化合物.与14种不同的取代苯基异氰酸酯反应,生成14种新化合物,产率中等.化合物3i经X射线单晶衍射分析表明其结构为N,N′-双(邻甲苯基)-3,6-二甲基-1,4-二氢-S-四嗪-1,4-二甲酰胺,这表明发生了重排.据1H NMR测定结果,对反应机理作了初步讨论.14种化合物体外抗癌活性检测表明部分化合物有强的生物活性.

关键词: 1, 6-二氢-S-四嗪, 1, 4-二氢-S-四嗪, 异氰酸酯, 晶体结构, 重排, 抗肿瘤活性

Abstract: 3,6-Dimethyl-1,6-dihydro-S-tetrazine reacts with phenyl isocyanate over different catalysts to afford different products. When using N,N-dimethylaniline as the catalyst, N-phenyl-1,6-dihydro-3,6-dimethyl-S-tetrazine-1-cabonamide was obtained; when using 4-dimethylaminopyridine (DMAP) as the catalyst, the new kind of compound was obtained. Using 14 different substituted phenyl isocyanates, 14 new compounds were prepared with a low or medial yield. The structure of compound 3i was determined by X-ray crystal analysis as N,N′-di(o-methylphenyl)-3,6-dimethyl-1,4-dicarbonamide. It shows that the catalytical rearrangement occurred. The mechanism was discussed briefly with aid of 1H NMR results. The anticancer activity of these new compounds were tested in vitro. And the results show that some of them have good bioactivity.

Key words: 1,6-Dihydro-S-tetrazine, 1,4-Dihydro-S-tetrazine, Isocyanate, Crystal structure, Rearrangement, Antitumour activity

中图分类号: 

TrendMD: