title: Preparation of N-alkyl 2-pyridones via a lithium iodide promoted O- to N-alkyl migration: scope and mechanism.
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.
authors.affiliation: Department of Chemistry and Biochemistry, Calvin College, 1726 Knollcrest Circle SE, Grand Rapids, Michigan 49546, USA.
authors.forename: Sarah Z
authors.initials: SZ
authors.lastname: Tasker
authors.forename: Michael A
authors.initials: MA
authors.lastname: Bosscher
authors.forename: Christina A
authors.initials: CA
authors.lastname: Shandro
authors.forename: Erica L
authors.initials: EL
authors.lastname: Lanni
authors.forename: Keun Ah
authors.initials: KA
authors.lastname: Ryu
authors.forename: Gregory S
authors.initials: GS
authors.lastname: Snapper
authors.forename: Jarrad M
authors.initials: JM
authors.lastname: Utter
authors.forename: Bruce A
authors.initials: BA
authors.lastname: Ellsworth
authors.forename: Carolyn E
authors.initials: CE
authors.lastname: Anderson
mesh_terms: D000478:Alkylation; D007454:Iodides / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007454:Iodides; D011728:Pyridones; D008094:Lithium