2016 journal article
Synthesis of C-4 Substituted Amido Nicotine Derivatives via Copper(I)- and (II)-Catalyzed Cross-Coupling Reactions
JOURNAL OF ORGANIC CHEMISTRY, 81(22), 11529–11534.
MeSH headings : Amides / chemistry; Carbon-13 Magnetic Resonance Spectroscopy; Catalysis; Copper / chemistry; Mass Spectrometry; Nicotine / chemical synthesis; Nicotine / chemistry; Proton Magnetic Resonance Spectroscopy
TL;DR:
The syntheses of seven novel amido nicotine derivatives 12-18 from (S)-nicotine are presented, providing a useful method for preparing C-4 amide-containing nicotine analogs.
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Source: Web Of Science
Added: August 6, 2018
The syntheses of seven novel amido nicotine derivatives 12-18 from (S)-nicotine are presented. (S)-Nicotine and (S)-6-chloronicotine derivatives were cross-coupled with the corresponding amides 6-10 at the C-4 position of the pyridine ring via copper(I)-mediated reactions. Derivatives 16-18 were also obtained via copper(II)-mediated reactions from (S)-nicotine containing a C-4 boronic acid pinacol ester group. The optimization of reaction conditions for both routes provided a useful method for preparing C-4 amide-containing nicotine analogs.