106932-14-3Relevant articles and documents
PYRIDINES. XIII - ACYLATION DE PYRIDYL-LITHIOENAMINES PRIMAIRES. SYNTHESE DE PYRIDYL-ENAMIDES ET DE NAPHTYRIDIN-1,6 ONES-5.
Compagnon, Paul-Louis,Gasquez, Francoise,Kimny, Tan
, p. 49 - 56 (2007/10/02)
The primary lithioenamine 4a is an ambivalent nucleophile resulting from the condensation of benzonitrile with 2-s-collidyllithium.Acylation of 4a by acetyl, benzoyl, N,N-dimethylcarbamoyl chlorides, ethyl chloroformate or methyl benzoate leads to β-C-acylated 5, N-acylated 6 (enamides) and β-C,N-diacylated 7 compounds.N-acylation predominates upon C-acylation with the studied aliphatic acid chlorides, contrary to benzoylation. 4,6-Dimethyl-2-pyridyl-acetate 17 and -acetamide 18 are formed and their origin is discussed.Thermocyclization of certain enamides, carbamates 6c, 7c and urea 6d leads to 2,4-dimethyl-7-phenyl-1,6-naphthyridin-5-(6H) ones 9a and 9b, and not to pyridopyrimidones 8.