Two
organic cages have been prepared in situ in water through the
2 + 3 hydrazone coupling of two pyridinium-derived trialdehydes and
oxalohydrazide. The highly water-soluble cages encapsulate and solubilize
linear neutral molecules. Such encapsulation has been applied for
the promotion of both two- or three-component hydrazone condensation
in water. For two-component reactions, the yields of the resulting
monohydrazones are increased from 5–10 to 90–96%. For
three-component reactions of hydrazinecarbohydrazide with 11 aromatic
aldehydes, in the presence of the organic cages, the bihydrazone products
can be produced in 88–96% yields. In contrast, without the
promotion of the organic cages, 9 of the reactions do not afford the
corresponding dihydrazone product.
Two
organic cages have been prepared in situ in water through the
2 + 3 hydrazone coupling of two pyridinium-derived trialdehydes and
oxalohydrazide. The highly water-soluble cages encapsulate and solubilize
linear neutral molecules. Such encapsulation has been applied for
the promotion of both two- or three-component hydrazone condensation
in water. For two-component reactions, the yields of the resulting
monohydrazones are increased from 5–10 to 90–96%. For
three-component reactions of hydrazinecarbohydrazide with 11 aromatic
aldehydes, in the presence of the organic cages, the bihydrazone products
can be produced in 88–96% yields. In contrast, without the
promotion of the organic cages, 9 of the reactions do not afford the
corresponding dihydrazone product.
Four new derivatives of 2-pyridine mono(thio)carbohydrazones were synthesized by condensation of carbaldehydes with carbohydrazide and thiocarbohydrazide following a known procedure. Compounds obtained were characterized using FT-IR, NMR, and UV-Vis spectroscopy, and their purity was determined by elemental analysis. Within the investigation of biological activity, four derivatives were subjected to antioxidative and antimicrobial studies, showing significant results. All obtained results concerning biological activity were supported by TD-DFT calculations. Comparing, monothiocarbohydrazones have shown much better activity than monocarbohydrazones. As a part of the characterization of potentially biologically active compounds ionization constants of synthesized compounds were theoretically predicted, experimentally determined and their mutual similarities i.e. differences were confirmed with NBO analysis.
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