10283-65-5Relevant articles and documents
From bipyridines to tobacco alkaloids and related compounds
Plaquevent, Jean-Christophe,Chichaoui, Ilhame
, p. 369 - 379 (2007/10/03)
Starting from structural considerations which led to the hypothesis that a chemical relationship could exist between two families of natural compounds (mainly pyridinic and pyrrolidinic alkaloids), experiments were carried out in order to establish a correlation route between the two studied classes. Of special interest was the central position of nicotine in these studies, and the main part of this work was devoted to the synthesis of nicotine starting from bipyridines. It was thus necessary to determine the conditions for selective reactions on one aromatic ring of bipyridines (N-methylation, N-oxidation and reduction of the heterocycle). Ring contraction procedure allowed us to obtain nicotine from the parent compound (3,3′-bipyridine). Complementary studies yielded various isomers of piperidinylpyridines (hexahydro derivatives of bipyridines) in a regiochemically controlled manner by means of original methods. Elsevier,.
