Synthesis and Reactivity of Azidoximes: III. 1-Azido(4-amino-1,2,5-oxadiazol-3-yl)aldoxime in the Cycloaddition Reaction

By 1,3-dipolar addition of 1-azido(4-amino-1,2,5-oxadiazol-3-yl)aldoxime to propargyl alcohol and phenylacetylene bicyclic 4-amino-1,2,5-oxadiazol-3-yl(4-R-1,2,3-triazol-1-yl)ketoximes were obtained which in reaction with acetic anhydride afforded the corresponding O-acyl derivatives. Diazotization of 4-amino-1,2,5-oxadiazol-3-yl(4-R-1,2,3-triazol-1-yl)ketoximes furnished 4-azido derivatives. The treatment of 4-amino-1,2,5-oxadiazol-3-yl(4-hydroxymethyl-1,2,3-triazol-1-yl)ketoxime with SOCl₂ resulted in 4-amino-1,2,5-oxadiazol-3-yl(4-chloromethyl-1,2,3-triazol-1-yl)ketoxime, whose chlorine atom was readily replaced by azide ion affording 4-amino-1,2,5-oxadiazol-3-yl(4-azidomethyl-1,2,3-triazol-1-yl)ketoxime.