969-51-7Relevant academic research and scientific papers
Reactivity of 2-benzylpyridyl lithium toward benzonitrile derivatives: Addition versus elimination
Hao, Xiaomin,Qin, Lu,Xu, Mali,Chen, Xia
, p. 168 - 177 (2017)
This work investigated the reactivity of 2-benzylpyridyl lithium (2-Pyr)C(Ph)(R)Li (R = SiMe3, Li1; R = H, Li2) toward benzonitrile derivatives. Based on the different products, the reaction between lithium salts and nitriles might involve in addition, elimination and bimolecular coupling pathways, respectively. Treatment of Li1 with ArCN (Ar = Ph, p-Tolyl, o-Tolyl, p-OMePh) yielded an addition intermediate pyridyl-1-aza-allyl-lithium [{(2-Pyr)C(Ph)C(Ar)N(SiMe3)}Li]2 (1, Ar = Ph) and its corresponding hydrolysis product 2-benzylpyridyl-ketone 2–5, respectively, in which the reaction involved in a 1,3-shift of -SiMe3 group to form a dimeric pyridyl-1-aza-allyl-lithium then followed by acidic hydrolysis. The MeOLi elimination reaction between Li2 and p-MeO(C6H4)CN resulted in formation of 4-(2-benzylpyridyl)benzonitrile 6. The reaction of Li2 with p-Me(C6H4)CN in the presence of TMEDA generated a 1:2 hydrolysis adduct 2-benzylpyridyl-enaminone 7, however, in the absence of TMEDA it afforded a coupling product of bimolecular nitriles, 1-(4-methylphenyl)-2-cyanophenyl-ethanone 8. We speculated the reaction mechanisms in sequence. The crystal structures of 1 and 5–8 were analyzed.
α-(2-Pyridine)benzyl aryl ketones as potential hypocholesteremic agents
Hewitt,Wade,Sinsheimer,Wang,Drach,Burckhalter
, p. 1339 - 1340 (2007/10/04)
A series of α-(2-pyridine)benzyl aryl ketones were prepared as potential hypocholesteremic agents. The synthesis of these compounds was by conversion of 2-benzylpyridine to its anion with n-butyllithium and condensation of the anion with selected aromatic esters. The ketones were tested for their hypocholesteremic activity in rats, and those compounds showing activity were further tested for estrogenicity. Only those aryl ketones with substituents in the ortho position showed a statistically significant reduction in serum cholesterol. Of these compounds the tert-butyl derivative had the most favorable hypocholesteremic to estrogenic ratio.
