Heterocycles from nitrile oxides. II . 1,2,4-oxadiazin-6-ones

Condensation of arylnitrile oxides with α-amino acid esters, other than those of glycine and analine, has been found to constitute a synthetic route to the hitherto unknown 1,2,4-oxadiazin-6-ones 7. α-Amino alcohols yield with nitrile oxides the corresponding acyclic N-(arylhydroxamoyl)amino alcohols, which are also accessible by borohydride reduction of compounds 7 . In contrast, the adducts formed from nitrile oxides and α-amino acids are unstable; they decompose readily into the aldehyde, derived from the amino acid, together with the aldoxime, derived from the nitrile oxide. Both decomposition products are also formed when compounds 7 are subjected to mild hydrolysis.