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Hemi-synthesis of novel chiral benzodiazepine derivatives from Eucalyptus citriodora essential oil: 2D NMR experiments and differential scanning calorimetry study of diastereoisomers.

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An efficient in situ condensation of citronellal, the main constituent of Eucalyptus citriodora essential oil (51%), with different amine derivatives of 2,3-diaminomaleonitrile and 3-[(2-aminoaryl)amino]dimedone has led to novel chiral benzodiazepine… Click to show full abstract

An efficient in situ condensation of citronellal, the main constituent of Eucalyptus citriodora essential oil (51%), with different amine derivatives of 2,3-diaminomaleonitrile and 3-[(2-aminoaryl)amino]dimedone has led to novel chiral benzodiazepine structures. All reactions were precipitated in ethanol and pure products were obtained in good yields (58-75%) without any purification. The synthesized benezodiazepines were characterized by spectroscopic techniques, namely 1H-NMR, 13C-NMR, 2D NMR and FTIR. Differential Scanning Calorimetry (DSC) and HPLC were used to confirm the formation diastereomeric mixtures of benzodiazepine derivatives.

Keywords: eucalyptus citriodora; novel chiral; essential oil; chiral benzodiazepine; differential scanning; citriodora essential

Journal Title: Natural product research
Year Published: 2023

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