58802-11-2Relevant articles and documents
Addition of novel benzylmagnesium “ate” complexes of BnR2MgLi type to 2-(thio)pyridones and related compounds
So?nicki, Jacek G.,Idzik, Tomasz,Borzyszkowska, Aleksandra,Wróblewski, Emil,Maciejewska, Gabriela,Struk, ?ukasz
, p. 481 - 493 (2017)
Novel benzylation reagents BnR2MgLi were obtained by mixing benzylmagnesium chloride (BnMgCl) and appropriate organolithium compounds (RLi). As BnR2MgLi complexes are more nucleophilic than the parent Grignard compound they enabled regioselective C6-addition to electrophilic N-substituted 2-(thio)-pyridones and C4-addition to poorly reactive NH 2-(thio)pyridones in high and good yields, respectively. Thus, the application of these new reagents in efficient synthesis of 6-benzyl-3,6-dihydro- and 4-benzyl-3,4-dihydropyridin-2(1H)-ones is described. The prospect of wider application of BnR2MgLi in 1,4-addition to other electrophiles, comprising six-membered α,β-unsaturated systems is also presented.
Preparation of N-alkyl 2-pyridones via a lithium iodide promoted oto N-alkyl migration: Scope and mechanism
Tasker, Sarah Z.,Bosscher, Michael A.,Shandro, Christina A.,Ryu, Keun Ah,Snapper, Gregory S.,Utter, Jarrad M.,Anderson, Carolyn E.,Lanni, Erica L.,Ellsworth, Bruce A.
, p. 8220 - 8230,11 (2020/10/15)
An efficient and inexpensive LiI-promoted O- to N-alkyl migration of 2-benzyloxy-, 2-allyloxy-, and 2-propargyloxypyridines and heterocycles is reported. The reaction produces the corresponding N-alkyl 2-pyridones and analogues under green, solvent-free conditions in good to excellent yields (30 examples, 20-97% yield). This method has been shown to be intermolecular and requires heat and lithium cation to occur.
