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Synthesis of C‑4 Substituted Amido Nicotine Derivatives via Copper(I)- and (II)-Catalyzed Cross-Coupling Reactions

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journal contribution
posted on 21.10.2016, 00:00 by Jiancheng Zhu, Monica F. Enamorado, Daniel L. Comins
The syntheses of seven novel amido nicotine derivatives 1218 from (S)-nicotine are presented. (S)-Nicotine and (S)-6-chloronicotine derivatives were cross-coupled with the corresponding amides 610 at the C-4 position of the pyridine ring via copper­(I)-mediated reactions. Derivatives 1618 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.