- Preparation of N-alkyl 2-pyridones via a lithium iodide promoted O- to N-alkyl migration: scope and mechanism.
Preparation of N-alkyl 2-pyridones via a lithium iodide promoted O- to N-alkyl migration: scope and mechanism.
The Journal of organic chemistry (2012-08-30)
Sarah Z Tasker, Michael A Bosscher, Christina A Shandro, Erica L Lanni, Keun Ah Ryu, Gregory S Snapper, Jarrad M Utter, Bruce A Ellsworth, Carolyn E Anderson
PMID22928642
ABSTRACT
An efficient and inexpensive LiI-promoted O- to N-alkyl migration of 2-benzyloxy-, 2-allyloxy-, and 2-propargyloxypyridines and heterocycles is reported. The reaction produces the corresponding N-alkyl 2-pyridones and analogues under green, solvent-free conditions in good to excellent yields (30 examples, 20-97% yield). This method has been shown to be intermolecular and requires heat and lithium cation to occur.
MATERIALS