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化学学报
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化学学报 ›› 1992, Vol. 50 ›› Issue (11): 1134-1139. 上一篇    下一篇

研究论文

低价钛引起的硝基酮还原成环反应

江建平;高炬;沈文斌;陈伟兴   

  1. 南京大学化学系
  • 发布日期:1992-11-15

Low-valent titanium induced reductive cyclization of nitroketone

JIANG JIANPING;GAO JU;SHEN WENBIN;CHEN WEIXING   

  • Published:1992-11-15

PDF

657

被引次数

22

在低价钛(TiCl~4-Zn)试剂作用下,4-硝基酮发生分子内还原成环反应,生成△'-吡咯啉.在同样条件下,4-硝基-1,7-二酮则可反应得到产率较高的8-氮杂双环[3.2.1]辛烷.该化合物具有颠茄生物碱母核结构,从而本文提供了合成这类化合物的新方法.

关键词: 氮杂二环辛烷, 四氯化钛, 颠茄碱, 硝基酮, 吡咯啉

The intramol. reductive cyclization of 4-nitro ketone with TiCl4-Zn reagent affords pyrrolines. Under the same condition, the reduction of 4-nitro-1,7-alkadione surprisingly gives in good yield the substituted 8-azabicyclo[3.2.1]octane, which has a skeleton of tropine alkaloid, therefore, this reaction provides a novel route to the tropine derivatives Thus, pyrroline I and azabicyclooctane II were prepared in 73.3 and 84.0% yield from BzCH2CH(Ph)CH2NO2 and (BzCH2CHPh)2CH2NO2, resp.

Key words: AZABICYCLOOCTANE, TITANIUM TETRACHLORIDE, BELLADONNA ALKALOIDS, NITROKETONE, PYRROLINE (=DIHYDROPYRROLE)

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