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.

By: J. Zhu n, M. Enamorado n & D. Comins n

co-author countries: United States of America 🇺🇸
MeSH headings : Amides / chemistry; Carbon-13 Magnetic Resonance Spectroscopy; Catalysis; Copper / chemistry; Mass Spectrometry; Nicotine / chemical synthesis; Nicotine / chemistry; Proton Magnetic Resonance Spectroscopy
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.