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We report here an ecient one-step synthesis of new [1,2,4]oxadiazolo [4,5-d][1,4]diazepines and [1,2,4]oxadiazolo [4,5-d][1,4]diazepine-8-spiro-5 H -isoxazolines by way of highly peri-, regioand diastereoselective 1,3-dipolar cycloadditions of mesitonitrile oxide to 1,7-dimethyl-2,3-dihydro-1H-1,4-diazepines. The structures were elucidated by spectral methods and X-ray crystallographic analysis. The regiochemistry of the cycloaddition is dictated by frontier orbital interactions.