Synthesis of C-4 substituted nicotine derivatives via an N-acylpyridinium salt of (S)-nicotine.
[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.
Comins
Daniel L
DL
Department of Chemistry, North Carolina State University, Raleigh, 27695-8204, USA. daniel_comins@ncsu.edu
King
Laura S
LS
Smith
Emilie D
ED
Février
Florence C
FC
D015394:Molecular Structure; D009538:Nicotine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D011726:Pyridinium Compounds / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry
C512816:4-(dimethylphenylsilyl)nicotine; C512814:4-hydroxynicotine; D011726:Pyridinium Compounds; D012821:Silanes; D009538:Nicotine; D013455:Sulfur