The reaction of 2-epoxyethylenepyridine 1-oxide (4), obtained by m-chloroperbenzoic acid oxidation of 2-vinylpyridine (2), with nitrogen, oxygen, and sulfur nucleophiles has been investigated. Reaction of 4 with cyclic or acyclic amines affords pyridylethanolamine 1-oxides 8 which on reductive deoxygenation using palladium-on-charcoal and hydrogen give rise to pyridylethanolamines 9. Similar reactions with sodium ethoxide and sodium thiophenol yield the respective ethyleneglycol 8f and thioethanol 8g derivatives.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.