Synthesis of C-4 Substituted Nicotine Derivatives via an N-Acylpyridinium Salt of (S)-Nicotine

Synthesis of C-4 Substituted Nicotine Derivatives via an N-Acylpyridinium Salt of (S)-Nicotine

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-...

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Veröffentlicht in:Organic letters 2005-10, Vol.7 (22), p.5059-5062
Hauptverfasser: Comins, Daniel L, King, Laura S, Smith, Emilie D, Février, Florence C
Format: Artikel
Sprache:eng
Schlagworte:
Molecular Structure
Nicotine - analogs & derivatives
Nicotine - chemical synthesis
Nicotine - chemistry
Pyridinium Compounds - chemistry
Silanes - chemistry
Sulfur - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0520469