通过（S）-尼古丁的N-酰基吡啶鎓盐合成C-4取代的尼古丁衍生物。

Synthesis of C-4 substituted nicotine derivatives via an N-acylpyridinium salt of (S)-nicotine.

作者信息

Comins Daniel L, King Laura S, Smith Emilie D, Février Florence C

机构信息

Department of Chemistry, North Carolina State University, Raleigh, 27695-8204, USA.

出版信息

Org Lett. 2005 Oct 27;7(22):5059-62. doi: 10.1021/ol0520469.

DOI:10.1021/ol0520469

PMID:16235957

Abstract

[reaction: see text] A variety of novel nicotine derivatives were prepared from (S)-nicotine via a two-step sequence. Addition of a cuprate reagent to an N-acylpyridinium salt of nicotine, followed by aromatization with elemental sulfur, afforded C-4 substituted nicotines in moderate to high yield. Using this method, 4-(dimethylphenylsilyl)nicotine was prepared and oxidized to afford (S)-4-hydroxynicotine.

摘要

[反应：见正文] 通过两步反应从（S）-尼古丁制备了多种新型尼古丁衍生物。将铜酸盐试剂加到尼古丁的N-酰基吡啶鎓盐上，随后用元素硫进行芳构化反应，以中等至高产率得到C-4位取代的尼古丁。使用该方法，制备了4-（二甲基苯基甲硅烷基）尼古丁并将其氧化得到（S）-4-羟基尼古丁。