Journal
TETRAHEDRON LETTERS
Volume 54, Issue 30, Pages 3926-3928Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.05.054
Keywords
2-Pyridone; Mitsunobu reaction; Ambident nucleophiles; N-alkylation; O-allcylation
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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. (C) 2013 Elsevier Ltd. All rights reserved.
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