title: Synthesis of C-4 Substituted Amido Nicotine Derivatives via Copper(I)- and (II)-Catalyzed Cross-Coupling Reactions.
abstract: 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.
authors: Department of Chemistry, North Carolina State University , Raleigh, North Carolina 27695-8204, United States.
authors: Jiancheng
authors: J
authors: Zhu
authors: Department of Chemistry, North Carolina State University , Raleigh, North Carolina 27695-8204, United States.
authors: Monica F
authors: MF
authors: Enamorado
authors: Department of Chemistry, North Carolina State University , Raleigh, North Carolina 27695-8204, United States.
authors: Daniel L
authors: DL
authors: Comins
mesh_terms: D000577:Amides / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D013058:Mass Spectrometry; D009538:Nicotine / Q000138:chemical synthesis* / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy
chemical_list: D000577:Amides; D009538:Nicotine; D003300:Copper