Facile Synthesis of 1,4,2-Dioxazines Using Aromatic Chlorooximes and 2-Chloroethanol/2-Chlorophenols

Abstract

A facile and mild strategy for the synthesis of 5,6-dihydro-1,4,2-dioxazines by the reaction of aromatic chlorooximes with 2-chloroethanol in presence of NaH at room temperature in a short period of time is developed. This strategy is further extended for the synthesis of substituted 1,4,2-dioxazines using aromatic chlorooximes and 2-chlorophenols. Similarly, 5,6-dihydro-1,4,2-dioxazepine was also synthesized using aromatic chlorooxime and 3-bromopropanol. The developed protocol is simple, efficient and produces environmentally benign byproducts.