化学学报 ›› 1998, Vol. 56 ›› Issue (1): 93-101. 上一篇    

研究论文

金属锡促进下含氮芳杂环化合物的选择性烯丙基化反应

周景尧;陈招根;贾瑜;吴世晖   

  1. 复旦大学化学系
  • 发布日期:1998-01-15

Metallic tin promoted allylation of azaaromatics in the presence of allkyl chloroformate

ZHOU JINGYAO;CHEN ZHAOGEN;JIA YU;WU SHIHUI   

  • Published:1998-01-15

本文报道了金属锡粉促进下含氮芳杂环的烯丙基化反应。在氯甲酸酯存在下, 利用烯丙基溴和金属锡原位生成的烯丙基锡试剂作为亲核试剂捕捉体系中的N-酰化季铵盐, 合成了一系列烯丙基取代N-酰基杂环衍生物。反应对于咪唑, 噻唑, 吡啶, 嘧啶等含氮含硫的杂环都适用, 并且对于巴豆基溴的反应表现出良好的区域选择性。

关键词: 氮杂环化合物, 锡, 咪唑, 嘧啶, 噻唑, 烯丙基化, 氯甲酸酯

In the presence of chloroformates, the in situ formed allylic stannanes trapped the N-alkoxycarbonyl salt of azaaromatics to give allylation products. Several kinds of azaaromatics were used as substrates, such as imidazole, benzothiazole, pyridine, pyrimidine, etc. The reaction of crotyl bromide showed high regioselectivity.

Key words: NITROGEN HETEROCYCLICS, TIN, IMIDAZOLE, PYRIMIDINE, THIAZOLE, ALLYLATION, CHLORO-CARBONIC ESTER

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