Zhai Hongbin, Liu Peng, Luo Shengjun, Fang Fang, Zhao Mingyue
Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, China 200032.
Org Lett. 2002 Dec 12;4(25):4385-6. doi: 10.1021/ol026876n.
[reaction: see text] The title compound, 2, has been synthesized in 45% overall yield in six steps from 3-bromopyridine. The hexahydropyrrolo[3,2-f]pyrindine skeleton was constructed from key intermediate 5, via intramolecular azomethine ylide-alkene [3 + 2] cycloaddition. The present work constitutes a general method for rapid assembly of other related tricyclic nicotine analogues.
[反应：见正文]标题化合物2已由3-溴吡啶经六步反应合成，总产率为45%。六氢吡咯并[3,2-f]吡啶骨架是由关键中间体5通过分子内偶氮甲碱叶立德-烯烃[3+2]环加成反应构建而成。本工作构成了快速组装其他相关三环尼古丁类似物的通用方法。
