The Mitsunobu reaction is well known for forming aryl ethers, and while the use of N-nucleophiles is less common, the Mitsunobu reaction has also been used to form C-N bonds using relatively acidic nitrogen-containing heterocycles such as indoles, benzimidazoles, and purines.   2-Pyridones exist as a mixture of both pyridone and hydroxypyridine tautomers, and we have observed the formation of both N- and O-alkylated products using Mitsunobu conditions.   We have investigated the factors influencing the ratio of N- and O-alkylation in the Mitsunobu reaction of 2-pyridones.  We have found that the ratio of products is strongly influenced by the substitution pattern on the pyridone ring.  The ratios of N- and O-alkylation products using various substituted pyridones will be discussed.

Comparison of <i>N</i>- vs. <i>O</i>-alkylation of 2-pyridones under Mitsunobu conditions

243rd National Meeting (2012)

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Comparison of N- vs. O-alkylation of 2-pyridones under Mitsunobu conditions