Abstract
A new aci-quinone compound, 4-(aci-nitro)-2-(methoxy)-5-(3-nitro-2-(nitrooxy)propyl)-cyclohexa-2,5- dienone (2), an analog to 4-(aci-nitro)-2-(carboxymethoxy)-5-(3-nitro-2-(nitrooxy)propyl)-cyclohexa-2,5-dienone (1), was successfully synthesized and fully characterized by spectroscopic methods. The reactions of 1 and 2 with various reagents such as hydroxylamine, acetic anhydride, semicarbazide and thiosemicarbazide were examined. The structure of 11 obtained new compounds was established by IR, 1H NMR, 13C NMR, HMBC and MS spectra. It was shown that the unstable, sensitive aci-quinone structure of compounds 1 and 2 can exist in anhydrous organic solvents such as AcOEt, EtOH but in the presence of water, H+, HO- or at high temperatures, the aci-quinone structure of both 1 and 2 tendentiously transformed into the more stable nitro-phenol form.
Keywords: Aci-nitro, aci-quinone, nitrophenol, eugenol, semicarbazone, thiosemicarbazone.
Graphical Abstract
Call for Papers in Thematic Issues
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
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