Synthesis of 2-Substituted Pyridines via a Regiospecific Alkylation, Alkynylation, and Arylation of Pyridine N-Oxides
Hans Andersson, Fredrik Almqvist* and Roger Olsson
*Department of Chemistry, Umeå University, SE-901 87 Umeå, Sweden, Email:
fredrik.almqvist
chem.umu.se
H. Andersson, F. Almqvist, R. Olsson, Org. Lett., 2007, 9, 1335-1337.
DOI: 10.1021/ol070184n
see article for more reactions
Abstract
Addition of Grignard reagents to pyridine N-oxides in THF at room temperature and subsequent treatment with acetic anhydride at 120°C afforded 2-substituted pyridines in good yields. By exchanging acetic anhydride for DMF in the second step, 2-substituted pyridine N-oxides were obtained, enabling the synthesis of 2,6-disubstituted pyridines.
see article for more examples
Key Words
Pyridines, N-Oxides, Microwave Synthesis, Grignard Reagents
ID: J54-Y2007-1050
