Synthesis, Structure, and Antimicrobial Activity of the Reaction Products of Chloronitro-Substituted Benzofurazanes and Benzofuroxanes with Morpholine

Abstract

New amination reactions of morpholine with a series of chloronitro-substituted benzofurazanes and -furoxanes were studied. The reactions of morpholine with 5,7-dichloro-4,6-dinitrobenzofuroxane and 4-chloro-5-nitro- and 5-chloro-4-nitrobenzofurazanes gave products of the aromatic nucleophilic substitution of the chlorine substituents in the nitrogenous heterocycles. The composition and structure of the products were established by chemical, physical, and physicochemical methods. The reaction of morpholine with 4,6-dinitrobenzofuroxane gave a stable Meisenheimer σ-complex, the structure of which was assessed by X-ray diffraction analysis. The synthesized compounds showed high antibacterial and antimycotic activities toward pathogenic human and animal microflora.