Synthesis of substituted N-benzyl pyridones via an O- to N-alkyl migration.
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.
Lanni
Erica L
EL
Department of Chemistry, Pomona College, 645 North College Avenue, Claremont, California 91711, USA.
Bosscher
Michael A
MA
Ooms
Bartel D
BD
Shandro
Christina A
CA
Ellsworth
Bruce A
BA
Anderson
Carolyn E
CE
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
D000438:Alcohols; D001593:Benzyl Compounds; D007454:Iodides; D018020:Lithium Compounds; D011725:Pyridines; D011728:Pyridones; D011743:Pyrimidines; D011744:Pyrimidinones; D011804:Quinolines; D015363:Quinolones