Construction of a 1,2-diazetidine core based on a multicomponent reaction of N,N′-(2,3-dimethylbutane-2,3-diyl)bis(hydroxylamine), arylglyoxals, and Meldrum's acid

Abstract

Assembly of a 1,2-diazetidine moiety on the basis of vicinal bis(hydroxylamines) was implemented for the first time. This transformation was demonstrated using the multicomponent condensation of N,N′-(2,3-dimethylbutane-2,3-diyl)bis(hydroxylamine) (BHA) with various arylglyoxals and Meldrum's acid as an example. It was found that the investigated process leads to zwitterionic 1,2-diazetidines containing a 1,3-dioxane-4,6-dione moiety. As a result of the performed research, a facile approach for the synthesis of target products was developed. We show that the application of acetonitrile as a solvent is the distinctive feature of the proposed method. A one-step synthetic protocol involving readily available starting compounds, simple reaction conditions, atom economy, and a convenient preparative procedure without chromatographic purification are advantages of the presented approach. The structure of one of the synthesized compounds was unambiguously confirmed by X-ray analysis.