H. J. Hertog, H. Plas, M. Pieterse
Sep 2, 2010
Citations
0
Influential Citations
15
Citations
Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
Reactions of 6-substituted derivatives of 2-halogenopyridines with potassium amide in liquid ammonia have been investigated. Together with aminations leading to the formation of 2-amino compounds, two unusual reactions were found to occur, i.e. reactions partially involving meta-rearrangement and conversions involving a ring transformation. The rearrangements took place in aminations of various substances (e.g. of 2-bromo-6-methylpyridine, 2-chloro-6-methylpyridine and 2-bromo-6-ethoxypyridine). Ring transformations occurred in aminations of 2,6-dibromo- and 2,6-dichloro-pyridine, 4-amino-2-methylpyrimidine being formed. The mechanism of the remarkable reaction last-mentioned is discussed.