79674-54-7Relevant articles and documents
A comparison of N- versus O-alkylation of substituted 2-pyridones under Mitsunobu conditions
Torhan, Matthew C.,Peet, Norton P.,Williams, John D.
supporting information, p. 3926 - 3928 (2013/07/26)
2-Pyridones are well-known ambident nucleophiles which are capable of reacting with electrophiles through either the nitrogen or oxygen atom to form N-alkyl-2-pyridones or 2-alkoxypyridines, respectively. It has been shown that the ratio of these products can be affected by a number of factors including the nature of the electrophile, the base used for deprotonation, and the solvent. We have now discovered a relationship between the ratio of N- and O-alkylation products and the nature of substituents on the pyridone ring when the Mitsunobu reaction is used to alkylate 2-pyridones.
