An Expeditious Method for the Preparation of 2-Hydroxy-l,4-dioxane and Its Use in Reductive Alkylation of Amines

摘要

Selective oxidation of diethylene glycol by a rutheni-um(VIII) species, obtained in situ from ruthenium(IH) chloride-sodium periodate in the presence of a catalytic quantity of water, affords a monoaldehyde in the form of the internal acetal 2-hydroxy-1,4-dioxane. This compound was used in reductive alkylations of selected primary and secondary amines, demonstrating its utility in the preparation of target structures with the 2-(2-hydroxy-ethoxy)ethylamino unit.The 2-(2-hydroxyethoxy)ethylamino unit represents a common structural element shared by many biologically active compounds of general formula 4 (Scheme 1). Our search through databases revealed about 400 structures that contain the 2-(2-hydroxyethoxy)ethylamino unit, including approximately 20 biologically active and 7 commercially available compounds. This structural unit is present in acridine derivatives with antiviral activity,1 as well as in monobenzhydrylpiperazines claimed as antihis-taminics with strong sedative action.