title: Synthesis of substituted N-benzyl pyridones via an O- to N-alkyl migration.
abstract: A new LiI-promoted O- to N-alkyl migration has been developed for the conversion of O-alkylated 2-hydroxy pyridines, quinolines, and pyrimidines to the corresponding N-alkylated heterocycles in good to excellent yields (57-99%). This method serves as an efficient means for the preparation of N-benzyl pyridones, quinolones, and pyrimidones.
authors.affiliation: Department of Chemistry, Pomona College, 645 North College Avenue, Claremont, California 91711, USA.
authors.forename: Erica L
authors.initials: EL
authors.lastname: Lanni
authors.forename: Michael A
authors.initials: MA
authors.lastname: Bosscher
authors.forename: Bartel D
authors.initials: BD
authors.lastname: Ooms
authors.forename: Christina A
authors.initials: CA
authors.lastname: Shandro
authors.forename: Bruce A
authors.initials: BA
authors.lastname: Ellsworth
authors.forename: Carolyn E
authors.initials: CE
authors.lastname: Anderson
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000478:Alkylation; D001593:Benzyl Compounds / Q000138:chemical synthesis*; D007454:Iodides / Q000737:chemistry; D018020:Lithium Compounds / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry; D011728:Pyridones / Q000138:chemical synthesis*; D011743:Pyrimidines / Q000737:chemistry; D011744:Pyrimidinones / Q000138:chemical synthesis; D011804:Quinolines / Q000737:chemistry; D015363:Quinolones / Q000138:chemical synthesis
chemical_list: D000438:Alcohols; D001593:Benzyl Compounds; D007454:Iodides; D018020:Lithium Compounds; D011725:Pyridines; D011728:Pyridones; D011743:Pyrimidines; D011744:Pyrimidinones; D011804:Quinolines; D015363:Quinolones