Zhu J1, Enamorado MF1, Comins DL1.
J Org Chem. 2016 Nov 18;81(22):11529-11534. Epub 2016 Nov 1.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.
Nizioł J1, Zieliński Z2, Leś A3, Dąbrowska M2, Rode W2, Ruman T4.
Bioorg Med Chem. 2014 Aug 1;22(15):3906-12. doi: 10.1016/j.bmc.2014.06.014. Epub 2014 Jun 16.By seeking new stable boron-containing nucleoside derivatives, potential BNCT boron delivery agents, a novel synthetic approach was tested, aimed at a boron attachment via a single bond to an aliphatic carbon of sp(3) hybridization. The latter allowed successful modification of deoxycytidine in the reaction with 2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane of the deoxynucleoside amino group. Read More