1,6-二氢-S-四嗪与异氰酸酯催化重排反应的研究  

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

作　　者：胡惟孝[1] 孙雅泉[1] 袁庆[1] 杨忠愚[1] 

机构地区：[1]浙江工业大学制药工程研究所,杭州310014

出　　处：《高等学校化学学报》2002年第10期1877-1881,共5页Chemical Journal of Chinese Universities

基　　金：浙江省自然科学基金 (2 0 0 0 16)资助

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 1 4种不同的取代苯基异氰酸酯反应 ,生成 1 4种新化合物 ,产率中等 .化合物 3 i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 1 H NMR测定结果 ,对反应机理作了初步讨论 .13,6-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.

关 键 词：重排反应 1 6-二氢-S-四嗪 1 4-二氢-S-四嗪 异氰酸酯 晶体结构 抗肿瘤活性 催化反应 

分 类 号：R979.1[医药卫生—药品] R914.4[医药卫生—药学]