 ISSN 0235-7216 ISSN 2424-4538 (online) |
2008 m. Nr. 1 Synthesis of 3-{[2-(N1-alkylidenehydrazinocarbonyl)ethyl](4-alkoxyphenyl)amino}propanohydrazide derivatives and analysis of their isomer composition
The compounds under study were synthesized from p-methoxyaniline and p-ethoxyaniline, the reaction of which with acrylic acid resulted in the formation of 3-[(2-carboxyethyl)(4-alkoxyphenyl) amino]propanoic acids; these products were transformed into dihydrazides, which during the condensation with cyclohexanone, acetone and ethyl methyl ketone yielded 3-{[2-(N1-alkylidenehydrazinocarbonyl)ethyl](4-alkoxyphenyl)amino}propanohydrazides. The molecular structure of the synthesized compounds is interesting due to the uniform disubstitution of their amine group with different sterical arrangement of the substituents. The chain of each side consists of amide and azomethine fragments able to form isomers. The structure elucidation and the behavior of isomer formation in the solvents of different polarity are discussed and rationalized in the present work combining the elemental analysis, mass, and 1H, 13C NMR spectroscopy with molecular modeling data. Keywords: amino acids, isomerization, amides, hydrazones, NMR spectroscopy, molecular modeling |
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