Double cyclization of O-acylated hydroxyamides generates 1,6-dioxa-3,9-diazaspiro[4.4]nonanes a new class of oxy-oxazolidinones

Abstract

An efficient synthetic route to the synthesis of a new class of oxy-oxazolidinones namely 1,6-dioxa-3,9-diazaspiro[4.4]nonanes via O-acylated α-hydroxyamides by a comparable strategy to the synthesis of cyclic orthoamides is presented. The optimum reaction conditions utilize an excess amount of each reagent to give the target molecules whereas using stoichiometric amounts of reagents with respect to the substrate furnishes silyl carbamates.