84737-97-3Relevant academic research and scientific papers
PYRIDINES, PARTIE X - SYNTHESE DE PYRIDYL- ET QUINOLYLENAMIDINES PAR CONDENSATION ENTRE COMPOSES ORGANOLITHIENS ET BENZONITRILE. NOVEAUX INTERMEDIAIRES POUR REACTIONS D'HETEROCYCLISATION
Compagnon, Paul-Luis,Gasquez, Francoise,Compagnon, Odette,Kimny, Tan
, p. 931 - 946 (2007/10/02)
A series of methylpyridyl- and (methyl)quinolylphenylvinylbenzamidines has been synthesized by condensation of organopolylithium compounds derived from polymethylpyridines and quinolines with benzonitrile.In diethyl ether, besides the enamidines, the reaction gives enolizable ketones.Triphenylimidazole, triphenyl-s-triazine and triphenylpyrimidine are isolated in the case of benzylmagnesium chloride.Possible routes leading to the various products are suggested.In diethyl ether, the conditions wich give the enamidine derivatives in useful yields have been established.In liquid ammonia, on the contrary, no polycondensed products were isolated.The intermediate enamine and enamidine anions are trapped in diethyl ether by acetylation of the reaction mixture before hydrolysis.With benzoyl or acetyl chloride, ethyl chloroformate, various C- and N-acylated products (enolizable β-diketones, enamides, acylenamides, N-acylenamidines) and their cyclization products (pyrimidines) are obtained.The latter are also prepared from the isolated enamidines and benzoyl chlorides.
