2-Amino-4-aryl-1-arylideneaminoimidazoles and Acylation Products: A Multinuclear (¹H, ¹³C, ¹⁵N) NMR Study

Summary.

The structure of 2-amino-4-aryl-1-arylideneaminoimidazoles in DMSO-d₆ solution was investigated by means of NMR spectroscopic methods (¹H, ¹³C, ¹⁵N). From these data the (E)-configuration at the excocyclic C=N bond and a strong preference for the conformer with the imidazole H-5 and the N=CH proton being spatially close (s-trans regarding the N–N bond) can be concluded. Reaction of the title compounds with acetic anhydride leads to mono and diacylation at the 2-amino group, whereas treatment with pivalic anhydride exclusively affords the corresponding monoacyl product. The mono- and diacylation products exhibit similar configurational and conformational properties as the parent compounds.