John Christopher Schmidhauser

A new preparation of N-Alkyl-2(1H)-pyridones from 2-glycidoxypyridines

Abstract N-Alkyl-2(1H)-pyridones are prepared in high yield by the reaction of 2-glycidoxypyridines with carboxylic acids, phenols or thiophenols. These reactions proceed through an oxazolinium ion intermediate, which reacts with the acid counter ion to give the ultimate products.

Rearrangement of 2-(haloalkoxy)pyridines to N-haloalkyl-2(1H)-pyridones

Abstract 2-(Haloalkoxy)pyridines thermally rearrange to N-haloalkyl-2(1H)-pyridones in high yield. The reaction rate is accelerated by use of a more polar solvent, by bromine rather than chlorine as the halogen substituent and by a two-carbon alkoxy chain as opposed to a three or, especially, four-carbon chain. The reaction kinetics can be interpreted in terms of an oxazolium ion intermediate.