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Regioselective Synthesis of 6‐Vinyl‐3,6‐dihydropyridine‐2(1 H )‐ones through Simple Addition of a Vinylmagnesium “Ate” Complex to 2‐Pyridones
Author(s) -
Sośnicki Jacek G.,
Dzitkowski Przemysław,
Struk Łukasz
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500605
Subject(s) - chemistry , regioselectivity , reagent , nucleophile , medicinal chemistry , lithium (medication) , ring (chemistry) , nitrogen atom , chloride , organic chemistry , catalysis , psychology , psychiatry
A highly nucleophilic vinylation reagent, lithium vinyldimethylmagnesate (vinylMe 2 MgLi), is obtained by mixing vinylmagnesium chloride (1 equiv.) and MeLi (in diethoxymethane; 2 equiv.). The application of this new reagent in the completely regioselective synthesis of 6‐vinyl‐3,6‐dihydro‐1 H ‐pyridin‐2(1 H )‐ones by simple 1,6‐additions to 2‐pyridones is described. Examination of the scope and limitations of the addition revealed the influence on the efficiency of the 6‐vinylation reaction of substituents on the nitrogen atom and on the 2‐pyridone ring.