Diastereotopic effect in some N-substituted-3-methyl-4,1-benzoxazepine-2,5-diones

1H NMR assignment of seven differently N-substituted-3-methyl-4,1-benzoxazepine-2,5-diones (I) revealed that with the exception of allyl, N-methylene protons of the substituents exhibit diastereotopy due to presence of a chiral centre in the heterocyclic ring at C-3. The significant finding is that the methylenes at C-2' in the substituents n-propyl and n-butyl (Id, Ie) also show diastereotopy. However, the one closer to the chiral centre (at C-1') exhibits greater non-equivalence of its protons. The diastereotopic methylene groups reported in this study correspond to the simplest system AB on one hand and as complex as ABMM'X2 or ABMM'X3 on the other. Calculated spectra obtained from assigned set of data for most of the coupled protons were in good agreement with the observed ones.